Best Middlesex County Hotels
🏨Here are some hot spots in Middlesex County and top picks for places to stay - each with its own vibe to match your travel style!
1. Postcard Cabins Machimoodus
• Starts at about €176. Guests give it 9.2/10 rating from 54 reviews.
• Just 0.37 km from Camp Chomeish of New England—super convenient!
2. Inn at Middletown
• Score your stay for just €154 to €629! Rated 8.8/10 based on 98 reviews.
• You’ll love standout features like Indoor swimming pool, Skiing, and Hiking.
3. Super 8 by Wyndham Cromwell/Middletown
• Rates typically range from €53 to €208, with a 6.4/10 rating based on 95 guest reviews.
• Conveniently located just 0.9 km from TRITAC Training Center.
4. Quality Inn Old Saybrook - Westbrook
• From €85, stay at this hotel with rating of 7.7/10, based on 101 reviews.
• Enjoy easy access to Reel Cast Charters, only 0.63 km away.
5. Courtyard Hartford Cromwell
• Starts at about €182. Guests give it 8.5/10 rating from 100 reviews.
• Enjoy perks like Indoor swimming pool, Sauna, and Gym.
The above hotel prices are from Trip.com, for June 23-June 29.
Enter your dates for prices and availability of the best hotels in Middlesex County.
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Amazing 9+Great 8+Good 7+Pleasant 6+Popular filters for Middlesex County
Free cancellationSmoking roomBarbecueSuite1 double bedHotelBreakfast includedProperty Type
HotelResortApartmentCountry houseBed and breakfastVacation homeChaletInnMotelProperty facilities & services
BarbecueWi-Fi in public areasParking availableFree parkingGolf course24-hour front deskSmoking areaLuggage storagePoolBarPets welcomeGymConference roomElevatorRestaurantSpaWake-up callSaunaEV charging stationairport transfers55 Best Hotels to Stay in Middlesex County
Trip.com brings you a curated list of top accommodations in Middlesex County, complete with reviews, price insights, and amenity highlights, making it easy to find the perfect place to stay.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Middlesex County
"It was a great experience it was raining and peaceful sleep"
Great
55 reviews
9.2/10
1 night
From €126
62
Hotels in Middlesex County
Gym
Wi-Fi in public areas
Golf course
+6
"This chain hotel is very good, the facilities are better, the bedding is more comfortable, the service is good, the breakfast is quite rich, the hotel location is also very good, the parking is very convenient, good"
100 reviews
6.6/10
1 night
From €78
71
Hotels in Middlesex County
Indoor swimming pool
Skiing
Hiking
+10
"First stay, bedding has dirty things, second stay is good"
Very Good
100 reviews
8.8/10
1 night
From €152
93
Hotels in Middlesex County
Private parking
Wake-up call
Wi-Fi in public areas
+6
"Good value for money, very good"
95 reviews
7.0/10
1 night
From €73
19
Hotels in Middlesex County
Gym
Private parking
Conference room
+3
"Ii was sick so I'm trying to reschedule my date please"
Very Good
101 reviews
8.7/10
1 night
From €200
72
Hotels in Middlesex County
Private parking
Luggage storage
Wi-Fi in public areas
+4
"The hotel is near highway & gas station, Supermarket, McDonald, StartBucks !"
95 reviews
6.4/10
1 night
From €61
99+
Hotels in Middlesex County
Indoor swimming pool
Sauna
Gym
+8
"Two thousand RMB a night is really only enough for a bed in downtown New York. The room is only 6 square meters, a tiny dwelling, and does not come with breakfast. Although the subway station is nearby, the subway line is complicated and the transportation is quite time-consuming and labor-intensive. Walking is the best option."
Very Good
100 reviews
8.5/10
1 night
From €187
84
Hotels in Middlesex County
No. 1 of 4-Star Select Hotels in ConnecticutGolf course
Sunbathing area
Indoor swimming pool
+14
The Saybrook Point Resort & Marina is an ideal spot for travelers wanting to discover the city. Visitors to Old Saybrook will find that the Saybrook Point Resort & Marina is a fantastic accommodation choice. From the hotel, Madison is approximately 26km away. The nearest railway station is Madison, approximately 26km away. There is no shortage of things to see in the area, with the Pavilion at Saybrook Point, Poverty Island Beach and Fort Saybrook Monument Park all nearby. At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. This Old Saybrook hotel features parking on site. When it comes to Old Saybrook hotels, the Saybrook Point Resort & Marina is highly regarded for its excellent facilities.
Amazing
99 reviews
9.6/10
1 night
From €296
56
Hotels in Middlesex County
Private parking
Wi-Fi in public areas
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park. This hotel is 1.9 mi (3.1 km) from Saybrook Country Barn and 2 mi (3.3 km) from Stay and Play LLC.
Make use of convenient amenities such as complimentary wireless internet access, a picnic area, and barbecue grills.
The front desk is staffed during limited hours. Free self parking is available onsite.
Make yourself at home in one of the 50 guestrooms featuring refrigerators and microwaves. 44-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include desks and coffee/tea makers, and housekeeping is provided on request.
Very Good
100 reviews
8.0/10
1 night
From €88
71
Hotels in Middlesex County
Private parking
Gym
Luggage storage
+6
"Dingy hallways detracted from an otrherwise excellent stay. Thank you!"
Good
101 reviews
7.7/10
1 night
From €100
Find your unique stays in Middlesex County
Immerse yourself in the vibrant atmosphere of Middlesex County with our handpicked accommodation options
Most-booked Middlesex County hotels
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Check out these top-booked hotels from the past 30 days!
8.3/10
59 reviewsCopper Beech Inn
Hotel near Essex
A popular choice among guests booking hotels in Essex
When you stay at Copper Beech Inn in Ivoryton, you'll be on a river, within a 5-minute drive of Ivoryton Playhouse and Museum of Fife and Drum. This hotel is 1.6 mi (2.5 km) from Essex Steam Train and 1.6 mi (2.5 km) from Connecticut Valley Railroad State Park Trail.
Pamper yourself with onsite massages or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, wedding services, and tour/ticket assistance.
Enjoy a satisfying meal at Copper Beech Inn serving guests of Copper Beech Inn. Wrap up your day with a drink at the bar/lounge. A complimentary full breakfast is served daily from 8:00 AM to 10:00 AM.
Featured amenities include a business center, luggage storage, and a safe deposit box at the front desk. Planning an event in Ivoryton? This hotel has 500 square feet (46 square meters) of space consisting of conference space and meeting rooms. Free self parking is available onsite.
Make yourself at home in one of the 22 guestrooms. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with separate bathtubs and showers feature complimentary toiletries and hair dryers. Conveniences include phones, as well as coffee/tea makers and irons/ironing boards.
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6.7/10
78 reviewsBest Way Inn
Hotel near Middlefield
A popular choice among guests booking hotels in Middlefield
Located in Rockfall, Best Way Inn is within a 5-minute drive of Kidcity Children's Museum and Wesleyan University. This motel is 2.8 mi (4.5 km) from Van Vleck Observatory and 2.9 mi (4.7 km) from Wadsworth Mansion.
Make use of convenient amenities, which include complimentary wireless internet access and a vending machine.
Take advantage of the motel's 24-hour room service.
Featured amenities include a 24-hour front desk and a vending machine. Free self parking is available onsite.
Make yourself at home in one of the 24 air-conditioned guestrooms. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Bathrooms with bathtubs or showers are provided. Conveniences include desks and irons/ironing boards, and housekeeping is provided daily.
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8.6/10
96 reviewsSolano Inn
Hotel near Portland
A popular choice among guests booking hotels in Portland
With a stay at Solano Inn in Portland, you'll be within a 15-minute walk of Connecticut River and Arrigoni Winery. This hotel is 3.4 mi (5.5 km) from Chris Cote's Toptracer Golf Range and Performance Center and 3.9 mi (6.2 km) from Brownstone Exploration & Discovery Park.
Make use of convenient amenities such as complimentary wireless internet access, a television in a common area, and a picnic area.
Featured amenities include express check-out, a 24-hour front desk, and laundry facilities. Free self parking is available onsite.
Make yourself at home in one of the 49 individually furnished guestrooms, featuring kitchenettes. 55-inch Smart televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include desks and separate sitting areas, and housekeeping is provided daily.
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8.8/10
97 reviewsWater's Edge Resort & Spa
Hotel near Westbrook
A popular choice among guests booking hotels in Westbrook
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets. This beach resort is 3.7 mi (6 km) from Harvey's Beach and 6 mi (9.7 km) from Essex Steam Train.
Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. You can soak up the sun at the private beach or enjoy other recreational amenities including outdoor tennis courts and an indoor pool. Additional features at this resort include complimentary wireless internet access, concierge services, and an arcade/game room.
Enjoy Italian cuisine at Dattilo's Fine Dining, one of the resort's 3 restaurants, or stay in and take advantage of the room service (during limited hours). Snacks are also available at the coffee shop/cafe. Unwind at the end of the day with a drink at the bar/lounge or the beach bar. Cooked-to-order breakfasts are available daily from 7 AM to 11 AM for a fee.
Featured amenities include a 24-hour business center, express check-out, and dry cleaning/laundry services. Planning an event in Westbrook? This resort has 30000 square feet (2787 square meters) of space consisting of a conference center and 8 meeting rooms. Free valet parking is available onsite.
Make yourself at home in one of the 190 guestrooms featuring refrigerators and iPod docking stations. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have designer toiletries and hair dryers. Conveniences include laptop-compatible safes and desks, as well as phones with free local calls.
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6.5/10
1 reviewsPassport Inn and Suites - Middletown
Hotel near Middletown
A popular choice among guests booking hotels in Middletown
Accommodations come equipped with all the conveniences required for a restful night's slumber.A selection of rooms at Passport Inn and Suites Middletown come furnished with air conditioning to cater to your needs and comfort.
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9.5/10
30 reviewsThe Bevin House Bed & Breakfast
Hotel near East Hampton
A popular choice among guests booking hotels in East Hampton
Located in East Hampton, The Bevin House Bed & Breakfast is in the historical district, within a 10-minute drive of Connecticut River and Comstock Bridge. This bed & breakfast is 2.6 mi (4.2 km) from Day Pond State Park and 4.2 mi (6.7 km) from Salmon River State Forest.
Take advantage of recreation opportunities such as a seasonal outdoor pool or take in the view from a terrace and a garden. Additional features at this Victorian bed & breakfast include complimentary wireless internet access, a fireplace in the lobby, and a picnic area.
A complimentary full breakfast is served daily from 8:30 AM to 10:00 AM.
Featured amenities include express check-out, complimentary newspapers in the lobby, and a library. This bed & breakfast has 3 meeting rooms available for events. Free self parking is available onsite.
Make yourself at home in one of the 5 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers. Conveniences include coffee/tea makers and complimentary bottled water, and housekeeping is provided once per stay.
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8.6/10
99 reviewsClinton Motel
Hotel near Clinton
A popular choice among guests booking hotels in Clinton
The Clinton Motel is an ideal spot for travelers wanting to discover the city. The Clinton Motel is an ideal choice for travelers who want to take in the sights and sounds of Clinton.
With Madison just 8km away and Tweed New Haven Airport only 34km away, transportation is very convenient. There is no shortage of things to see in the area, with the Clinton Bible Fellowship, Rock and Roll Charters and Vox Church all nearby.
At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. This Clinton hotel provides parking on site.
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9.6/10
99 reviewsThe Captain Stannard
Hotel near Westbrook
A popular choice among guests booking hotels in Westbrook
Located in Westbrook (Westbrook Center), The Captain Stannard is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets. This bed & breakfast is 3.1 mi (4.9 km) from Clinton Plaza Shopping Center and 3.5 mi (5.6 km) from Chalker Beach.
Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional features at this Georgian bed & breakfast include a television in a common area, a picnic area, and bike parking.
A complimentary continental breakfast is served daily from 8:30 AM to 9:30 AM.
Featured amenities include express check-out and refrigerator in a common area. Guests may use a roundtrip airport shuttle for a surcharge, and free self parking is available onsite.
Make yourself at home in one of the 11 air-conditioned rooms featuring iPod docking stations. Complimentary wireless internet access is available to keep you connected. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include complimentary bottled water, and housekeeping is provided on request.
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9.8/10
51 reviewsWestbrook Inn B&B
Hotel near Westbrook
A popular choice among guests booking hotels in Westbrook
The Westbrook Inn B&B provides a great place for travelers to relax after a busy day. The Westbrook Inn B&B offers a pleasant stay in Westbrook for those traveling for business or leisure.
The hotel is conveniently located just 15km from Madison and 39km from Tweed New Haven Airport. With multiple attractions nearby including Stewart B. McKinney National Wildlife Refuge - Salt Meadow Unit, Stannard Beach and Westbrook Parks & Recreation, guests will find plenty to keep themselves occupied.
When guests have some time on their hands they can make use of the onsite facilities. This Westbrook hotel provides parking on site.
There's never a dull moment at this hotel, our guests indicate that the facilities are excellent.
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6.4/10
78 reviewsLamplighter Motel - Clinton, Connecticut
Hotel near Clinton
A popular choice among guests booking hotels in Clinton
With a stay at Lamplighter Motel - Clinton, Connecticut in Clinton, you'll be a short 5-minute walk from Clinton Plaza Shopping Center and within 2 minutes by car from Adam Stanton House and General Store Museum. This motel is 1.5 mi (2.5 km) from Clinton Town Beach and 1.6 mi (2.5 km) from Indian River Marina.
Free self parking is available onsite.
Make yourself at home in one of the 15 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and toothbrushes and toothpaste.
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Handpicked budget hotels in Middlesex County
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Affordable stays in Middlesex County, selected for value, comfort, and convenient locations.
10/10
15 reviewsSpacious Yard and View of Long Island Sound- Walk to Secluded Beach!
Hotel near Westbrook
Relaxing 4 Bedroom house with two baths and an outdoor shower on a double lot. Sleeps 8 comfortably. The house is surrounded by blueberry bushes which will supply berries for breakfast many summer mornings in July and August!! Walk to the beach just down the sidewalk - only seven houses away!! The beach is private for the community. There are also rocks to crab and dive from. The beach is self contained in a cove. House includes a dining room and a screened porch for game playing and reading. Many games and puzzles are available in the book shelves. The large yard provides room for a fire pit, games such as corn hole, croquet, frisbee etc. In the winter the fireplace is available for use with permission.
The house includes a washer and dryer, two Smart TV's and fast internet. The house is located near Water’s Edge resort, fine restaurants and excellent shopping. The house is only a short distance from Essex and Old Saybrook by car. Both historic towns to visit and enjoy. The train to New York and Boston is nearby via the stations in Westbrook and Old Saybrook. The town of Mystic is only 30 miles away to the East. Mystic is the home of the Mystic Seaport and Mystic Aquarium. 20 miles to the West is Yale University and the city of New Haven. Famous Wooster Street is worth a visit by car. Home of the birthplace of American Pizza.
About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Smoking allowed in yard.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
The house includes a washer and dryer, two Smart TV's and fast internet. The house is located near Water’s Edge resort, fine restaurants and excellent shopping. The house is only a short distance from Essex and Old Saybrook by car. Both historic towns to visit and enjoy. The train to New York and Boston is nearby via the stations in Westbrook and Old Saybrook. The town of Mystic is only 30 miles away to the East. Mystic is the home of the Mystic Seaport and Mystic Aquarium. 20 miles to the West is Yale University and the city of New Haven. Famous Wooster Street is worth a visit by car. Home of the birthplace of American Pizza.
About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Smoking allowed in yard.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
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9.8/10
0 reviewsLake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Hotel near Haddam
Lakefront! Look no further than our tranquil home on beautiful Hidden Lake! What a gem! Relax with the whole family as you sit by the fire pit and enjoy the sights and sounds of nature on the lakefront.
It's the perfect waterfront getaway, only a short distance from CT's most popular attractions: the CT River, Gilette Castle, The Goodspeed Opera House, and the world famous Mohegan Sun and Foxwoods Casinos.
With plenty of space for everyone, come have a vacation you won't forget.About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Paddle boat limited to 350lbs combined maximum weight load Kayaks limited to one passenger at a time.Do not keep windows and / or doors to the outside or the to the enclosed porch open during winter stays or while the heating system is running.,Please do not allow children to play / climb on the retaining wall and fence.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
It's the perfect waterfront getaway, only a short distance from CT's most popular attractions: the CT River, Gilette Castle, The Goodspeed Opera House, and the world famous Mohegan Sun and Foxwoods Casinos.
With plenty of space for everyone, come have a vacation you won't forget.About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Paddle boat limited to 350lbs combined maximum weight load Kayaks limited to one passenger at a time.Do not keep windows and / or doors to the outside or the to the enclosed porch open during winter stays or while the heating system is running.,Please do not allow children to play / climb on the retaining wall and fence.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
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10/10
24 reviewsSummer at the Haddam House
Hotel near Haddam
You cannot miss this beautifully renovated waterfront cottage in Haddam with stunning views of the East Haddam Swing Bridge, Goodspeed Opera House and The Gelston House. Watch float planes come in and out from the certified landing strip on the CT RIver. There is a deep water dock for larger boats and a "No Wake" zone to further enhance the peace and tranquility of your private spot. Enjoy your own private beach, patio with firepit and step down dock for provided kayak and your own jetskis. If you would like to bring your boat and or jetskis and use the deep water dock please inquire to the availability of doing so.
The cottage comes equipped with central air, Kureg brewing station and wifi to help with modern day essentials. Bordering Eagle Landing State Park, this is a nature lover's dream. Enjoy a cup of coffee on your own private dock while the fish jump and the Eagles soar. Step back in time at the Goodspeed Station, browse their many items and take a ride on The Essex Steam Train. If the water suits your fancy, hop on one of the many river cruise offerings all with in a short walk from you home away from home. We welcome you to our "Haddam House" where there is so much to see and do!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Quiet hours between 10:30pm and 7:00am..No guests besides the ones renting the property. No firewood is provided but can be purchased locally.,Parking for 2 cars in front of house..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
The cottage comes equipped with central air, Kureg brewing station and wifi to help with modern day essentials. Bordering Eagle Landing State Park, this is a nature lover's dream. Enjoy a cup of coffee on your own private dock while the fish jump and the Eagles soar. Step back in time at the Goodspeed Station, browse their many items and take a ride on The Essex Steam Train. If the water suits your fancy, hop on one of the many river cruise offerings all with in a short walk from you home away from home. We welcome you to our "Haddam House" where there is so much to see and do!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Quiet hours between 10:30pm and 7:00am..No guests besides the ones renting the property. No firewood is provided but can be purchased locally.,Parking for 2 cars in front of house..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
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9.8/10
40 reviewsAuthentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Hotel near Old Saybrook
Gather your people at our 1795 historic homestead near Coastal Connecticut, ideal for reunions, retreats & wedding weekends. Cook & linger in the well-stocked kitchen, read fireside or spread out across the private lawn and porches. A character-rich, memory-making home!
⭐ “Full of character, spacious and comfortable—our family loves coming back.” – Stephen
🏜 HIGHLIGHTS
✓ Authentic 1795 historic estate
✓ Private grounds, porches, firepit
✓ Well-stocked kitchen & cozy fireside spaces
THE SPACE
***Message us for weddings or other large events!***
Historic charm with private grounds, fireside rooms, porches, and a cook-ready kitchen.
🏷 Main Floor
Kitchen & Dining Room
∙ FULLY stocked kitchen w/plenty of counterspace for at-home baking and cooking
coffee maker, tea kettle, blender and toaster
∙ Cooking oils and seasoning essentials
∙ Abundance of dishware, glassware and silverware, including children’s
∙ Full-sized fridge and freezer
∙ Gas stove and oven
∙ Microwave
∙ Dishwasher
∙ Blender
∙ Slow cooker
∙ Dining room table, seating for 4
Living Room
∙ Smart TV
∙ Netflix, Prime Video, Disney Plus, Hulu, HBO and more
∙ Sound system
∙ Fireplace
∙ Board games
∙ Books
∙ Toys
Bedroom #1 (Primary Bedroom)
∙ King size bed
∙ Premium mattress and comforter
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books
∙ Mirror
Bedroom #2
∙ Queen size bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
Bedroom #3
∙ 2 Double beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books
Bathroom #1 and Laundry Room
∙ GE high-efficiency washer/dryer
∙ Tide Free and Gentle
∙ Shower
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth
Bathroom #2
∙ Shower
∙ Bathtub
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth
🏷 2nd Floor
Bedroom #4
∙ Double bed
∙ Single bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
Bedroom #5
∙ Queen size bed
∙ 2 Single beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Ceiling fan
∙ Full-length mirror
Hallway
∙ Office table and chair
🏷 Outdoor Space(s)
Sunroom
∙ Large glass roof for natural sunlight
∙ Comfortable sofa
∙ Rocking chair
Backyard
∙ Firepit
∙ Outdoor seating
∙ Play area
∙ Picnic tables and umbrella
Balcony
∙ Outdoor seating
∙ Coffee table
Porch
∙ Enclosed porch
∙ Outdoor seating
🏷 Parking
∙ Room for 6 vehicles but can hold up to 50+ for large events (contact us for details)
🚘 Nearby
Main Street Shops & Boutiques (walking ~3 min): Charming local shopping, antiques, galleries and cafés in the heart of Old Saybrook.
Ashlawn Farm Coffee (drive ~2 min): Local favorite café with specialty coffee, pastries, sandwiches and outdoor seating.
Monkey Farm (drive ~3 min): Popular bar & grill with classic fare and laid-back vibe.
Paperback Cafe (drive ~3 min): Cozy breakfast/brunch spot with community favorites.
Swell (drive ~3 min): Highly rated acai & healthy café option on Main Street.
James Pharmacy Bed & Breakfast and Gelateria (drive ~4 min): Historic gelato and coffee stop with old-town charm.
Fresh Salt (drive ~5 min): Upscale seafood dining with seasonal and local offerings.
Cafe Toscana (drive ~4 min): Casual coffee & tea spot for daytime breaks.
Otter Cove Restaurant & Bar (drive ~7 min): Stylish gastropub with seasonal local menus.
Saybrook South Green & Historic Sites (drive ~5 min): Historic district featuring the Humphrey Pratt Tavern and heritage architecture.
The Kate – Katharine Hepburn Cultural Arts Center (drive ~4 min): Live theater, arts and tribute exhibits to the legendary actress.
Saybrook Breakwater Light (drive ~6 min): Iconic sparkplug lighthouse and peaceful waterfront setting.
Lynde Point Light (drive ~6 min): Historic Long Island Sound lighthouse ideal for photography and scenic views.
Old Saybrook Town Beach (drive ~7 min): Saltwater beach with seasonal swimming and sunbathing.
Harvey’s Beach (drive ~9 min): Popular sandy shore and summer gathering spot on Long Island Sound.
Crystal Lake Town Park (drive ~5 min): Community park with playgrounds, trails and open recreational space.
Tanger Outlets Westbrook (drive ~7 min): Outlet shopping with over 150 brands for fashion and gifts.
Rocky Neck State Park (drive ~15 min): Beach, camping, hiking and nature trails.
Hammonasset Beach State Park (drive ~26 min): Connecticut’s largest shoreline park with miles of sandy beach and boardwalk.
Essex Village (drive ~20 min): Historic small town with antique shops, riverfront views and dining (great half-day trip).
💡 Other things to note
✓ This is a true historic home, full of charm and character, which means you may notice older-home quirks that come with a property from the late 1700s.
✓ The home sits near a main road, so you may hear some traffic at times, though the yard and grounds feel private once you’re settled in.
✓ The beach is ~5 minute drive from the property.
✓ Some areas on the property are reserved for caretaking and maintenance use and aren’t accessible to guests.About pets:No pets allowed, service animals permitted.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No smoking in the house or green house.Please keep the door to the house shut, either A/C,Please put things back where you have found them..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 50.
⭐ “Full of character, spacious and comfortable—our family loves coming back.” – Stephen
🏜 HIGHLIGHTS
✓ Authentic 1795 historic estate
✓ Private grounds, porches, firepit
✓ Well-stocked kitchen & cozy fireside spaces
THE SPACE
***Message us for weddings or other large events!***
Historic charm with private grounds, fireside rooms, porches, and a cook-ready kitchen.
🏷 Main Floor
Kitchen & Dining Room
∙ FULLY stocked kitchen w/plenty of counterspace for at-home baking and cooking
coffee maker, tea kettle, blender and toaster
∙ Cooking oils and seasoning essentials
∙ Abundance of dishware, glassware and silverware, including children’s
∙ Full-sized fridge and freezer
∙ Gas stove and oven
∙ Microwave
∙ Dishwasher
∙ Blender
∙ Slow cooker
∙ Dining room table, seating for 4
Living Room
∙ Smart TV
∙ Netflix, Prime Video, Disney Plus, Hulu, HBO and more
∙ Sound system
∙ Fireplace
∙ Board games
∙ Books
∙ Toys
Bedroom #1 (Primary Bedroom)
∙ King size bed
∙ Premium mattress and comforter
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books
∙ Mirror
Bedroom #2
∙ Queen size bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
Bedroom #3
∙ 2 Double beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books
Bathroom #1 and Laundry Room
∙ GE high-efficiency washer/dryer
∙ Tide Free and Gentle
∙ Shower
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth
Bathroom #2
∙ Shower
∙ Bathtub
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth
🏷 2nd Floor
Bedroom #4
∙ Double bed
∙ Single bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
Bedroom #5
∙ Queen size bed
∙ 2 Single beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Ceiling fan
∙ Full-length mirror
Hallway
∙ Office table and chair
🏷 Outdoor Space(s)
Sunroom
∙ Large glass roof for natural sunlight
∙ Comfortable sofa
∙ Rocking chair
Backyard
∙ Firepit
∙ Outdoor seating
∙ Play area
∙ Picnic tables and umbrella
Balcony
∙ Outdoor seating
∙ Coffee table
Porch
∙ Enclosed porch
∙ Outdoor seating
🏷 Parking
∙ Room for 6 vehicles but can hold up to 50+ for large events (contact us for details)
🚘 Nearby
Main Street Shops & Boutiques (walking ~3 min): Charming local shopping, antiques, galleries and cafés in the heart of Old Saybrook.
Ashlawn Farm Coffee (drive ~2 min): Local favorite café with specialty coffee, pastries, sandwiches and outdoor seating.
Monkey Farm (drive ~3 min): Popular bar & grill with classic fare and laid-back vibe.
Paperback Cafe (drive ~3 min): Cozy breakfast/brunch spot with community favorites.
Swell (drive ~3 min): Highly rated acai & healthy café option on Main Street.
James Pharmacy Bed & Breakfast and Gelateria (drive ~4 min): Historic gelato and coffee stop with old-town charm.
Fresh Salt (drive ~5 min): Upscale seafood dining with seasonal and local offerings.
Cafe Toscana (drive ~4 min): Casual coffee & tea spot for daytime breaks.
Otter Cove Restaurant & Bar (drive ~7 min): Stylish gastropub with seasonal local menus.
Saybrook South Green & Historic Sites (drive ~5 min): Historic district featuring the Humphrey Pratt Tavern and heritage architecture.
The Kate – Katharine Hepburn Cultural Arts Center (drive ~4 min): Live theater, arts and tribute exhibits to the legendary actress.
Saybrook Breakwater Light (drive ~6 min): Iconic sparkplug lighthouse and peaceful waterfront setting.
Lynde Point Light (drive ~6 min): Historic Long Island Sound lighthouse ideal for photography and scenic views.
Old Saybrook Town Beach (drive ~7 min): Saltwater beach with seasonal swimming and sunbathing.
Harvey’s Beach (drive ~9 min): Popular sandy shore and summer gathering spot on Long Island Sound.
Crystal Lake Town Park (drive ~5 min): Community park with playgrounds, trails and open recreational space.
Tanger Outlets Westbrook (drive ~7 min): Outlet shopping with over 150 brands for fashion and gifts.
Rocky Neck State Park (drive ~15 min): Beach, camping, hiking and nature trails.
Hammonasset Beach State Park (drive ~26 min): Connecticut’s largest shoreline park with miles of sandy beach and boardwalk.
Essex Village (drive ~20 min): Historic small town with antique shops, riverfront views and dining (great half-day trip).
💡 Other things to note
✓ This is a true historic home, full of charm and character, which means you may notice older-home quirks that come with a property from the late 1700s.
✓ The home sits near a main road, so you may hear some traffic at times, though the yard and grounds feel private once you’re settled in.
✓ The beach is ~5 minute drive from the property.
✓ Some areas on the property are reserved for caretaking and maintenance use and aren’t accessible to guests.About pets:No pets allowed, service animals permitted.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No smoking in the house or green house.Please keep the door to the house shut, either A/C,Please put things back where you have found them..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 50.
Select dates to view prices
10/10
18 reviewsFamily Stays: Middletown, CT
Hotel near Middletown
Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our space is perfect for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you’re exploring Middletown or nearby Connecticut towns, you’ll have the entire home to yourself for a fantastic experience.
The space:
Bedrooms: 4 bedrooms - 2 Queen beds on the 1st floor, 2 Twin beds on the 2nd floor, and 1 Queen bed on the 2nd floor.
Bathrooms: Full bathrooms on each floor.
Living Room: Ample space and a large Smart TV with Roku.
Kitchen: Well-equipped with appliances and cookware.
Dining Area: Seats 6 comfortably. Can accommodate up to 8 people with the table extension.
Climate Control: Mitsubishi Electric Split A/C units in bedrooms, living room, and dedicated workspace.
Laundry: Washer and dryer in the basement.
Family-Friendly: High chairs, toddler booster seat, Pack 'n Play, and playpen available for young guests. Shower chair is also available.
Outdoor Relaxation: Enclosed back porch and deck facing the backyard.
Guest access
- Enjoy the full use of the home, including a fenced backyard that borders the woods, providing an ideal space for children to play and run around.
- Self check-in key code entry.
- A 2-car garage and a spacious driveway for extra vehicles.
Other things to note.
Registered guests:
Only those listed on the reservation are permitted to stay overnight at the property.
Maximum Guests: 8 adults.
Reservation and Extra Guests Compliance:
Failure to adhere to our reservation limit or undisclosed additional guest policy will result in full extra guest charges per night, plus an additional 25% penalty.
Safety Measures:
Our property features Ring security cameras. These cameras are external and outward-facing, ensuring privacy within interior spaces. They record video and sound when activated by motion.
Smoking Policy:
Smoking or vaping is not allowed inside the house. A $500 cleaning fee will be assessed for deep cleaning to remove any smoke odor before the next guest checks in. However, you’re welcome to smoke outside in the breezeway - an attached room by the garage. Please use the provided ashtray.
Location and neighborhood:
Our home is conveniently located near the downtown area and the recently updated Veterans Memorial Park swimming pool with a splash pad.
Abundant restaurants, grocery stores, and pharmacies are within easy walking distance.
The home is available for short-term rentals and mid-term stays.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
The space:
Bedrooms: 4 bedrooms - 2 Queen beds on the 1st floor, 2 Twin beds on the 2nd floor, and 1 Queen bed on the 2nd floor.
Bathrooms: Full bathrooms on each floor.
Living Room: Ample space and a large Smart TV with Roku.
Kitchen: Well-equipped with appliances and cookware.
Dining Area: Seats 6 comfortably. Can accommodate up to 8 people with the table extension.
Climate Control: Mitsubishi Electric Split A/C units in bedrooms, living room, and dedicated workspace.
Laundry: Washer and dryer in the basement.
Family-Friendly: High chairs, toddler booster seat, Pack 'n Play, and playpen available for young guests. Shower chair is also available.
Outdoor Relaxation: Enclosed back porch and deck facing the backyard.
Guest access
- Enjoy the full use of the home, including a fenced backyard that borders the woods, providing an ideal space for children to play and run around.
- Self check-in key code entry.
- A 2-car garage and a spacious driveway for extra vehicles.
Other things to note.
Registered guests:
Only those listed on the reservation are permitted to stay overnight at the property.
Maximum Guests: 8 adults.
Reservation and Extra Guests Compliance:
Failure to adhere to our reservation limit or undisclosed additional guest policy will result in full extra guest charges per night, plus an additional 25% penalty.
Safety Measures:
Our property features Ring security cameras. These cameras are external and outward-facing, ensuring privacy within interior spaces. They record video and sound when activated by motion.
Smoking Policy:
Smoking or vaping is not allowed inside the house. A $500 cleaning fee will be assessed for deep cleaning to remove any smoke odor before the next guest checks in. However, you’re welcome to smoke outside in the breezeway - an attached room by the garage. Please use the provided ashtray.
Location and neighborhood:
Our home is conveniently located near the downtown area and the recently updated Veterans Memorial Park swimming pool with a splash pad.
Abundant restaurants, grocery stores, and pharmacies are within easy walking distance.
The home is available for short-term rentals and mid-term stays.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Select dates to view prices
10/10
1 reviewsBest of Both Worlds
Hotel near Old Saybrook
Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park!
The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun.
We’ve made great memories there over the years and are now looking to share it with others!
The space
The house is quaint with lots of sunlight- a mix of old and new!
Other things to note
Beach Access:
If you plan on driving to the beach you can either pay a daily fee or if you are staying for at least 1 week you can purchase a beach pass to access Harvey’s beach! Renters staying at least 1 week can purchase a 2 week beach pass starting April 15th, 2021. I will send instructions directly to renters once you have confirmed your stay!
If you walk or bike to the beach it is free.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun.
We’ve made great memories there over the years and are now looking to share it with others!
The space
The house is quaint with lots of sunlight- a mix of old and new!
Other things to note
Beach Access:
If you plan on driving to the beach you can either pay a daily fee or if you are staying for at least 1 week you can purchase a beach pass to access Harvey’s beach! Renters staying at least 1 week can purchase a 2 week beach pass starting April 15th, 2021. I will send instructions directly to renters once you have confirmed your stay!
If you walk or bike to the beach it is free.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Select dates to view prices
9.6/10
0 reviewsDriftwood Cottage @ Saybrook Point Marina, 2 King Beds
Hotel near Old Saybrook
Nestled between the Long Island Sound and the Connecticut River, Cove Street Cottage is your luxury getaway. You won’t have to pack a thing when you stay at this fabulous cottage-- linens, bikes, and chairs are all included. The charming upstairs master suite has a full bathroom and king bed, while the downstairs hosts two (2) additional bedrooms. Cozy up in the backyard by the fire pit, or adventure right across the street to the Saybrook Point Resort and Marina. Whether you are docking for the weekend or attending an event, you are just steps away. Ideal for 4 people, but can fit up to 6.
Soak up the friendliness of this small town, the breathtaking marina vistas, and glimpses of rich history throughout the area. Enjoy the many amenities of the resort on your doorstep, including its spa or award-winning dining at Fresh Salt. Beaches, Main Street, shopping and historic stops are all nearby. Come enjoy this coastal treasure!About pets:Pets allowed: limit 2 total.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Soak up the friendliness of this small town, the breathtaking marina vistas, and glimpses of rich history throughout the area. Enjoy the many amenities of the resort on your doorstep, including its spa or award-winning dining at Fresh Salt. Beaches, Main Street, shopping and historic stops are all nearby. Come enjoy this coastal treasure!About pets:Pets allowed: limit 2 total.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Select dates to view prices
10/10
25 reviewsBeach House steps to private beaches in sought after location!
Hotel near Old Saybrook
You will fall in love with this beautiful beach house in the sought-after Indian Town beach. Beautiful views of Harvey Beach, a comfortable outdoor area to relax and spend time with your family, two private beaches with a harbor that has panoramic views of Long Island Sound less than a 2-minute walk away!
Enjoy the small-town feel of a great community where you can walk bike, swim. Spectacular low tides await you!
Restaurants, outlets, and attractions all nearby. Perfect location to explore the Ct Shoreline.
This home is our happy place, and we look forward to sharing it with you!
Important - House is Fema Certified, so the living area is on the upper level. There is not ground-level living space, and there is an exterior staircase.
Small well-trained pet welcome! An additional deposit/cleaning fee,
Important Note: Garage is storage, not for parking guest automobiles.
Golf cart is not available for use.About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Traveler must engage in a conversation with the host about their group upon booking request..About checkIn:Check in after 4:30 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Enjoy the small-town feel of a great community where you can walk bike, swim. Spectacular low tides await you!
Restaurants, outlets, and attractions all nearby. Perfect location to explore the Ct Shoreline.
This home is our happy place, and we look forward to sharing it with you!
Important - House is Fema Certified, so the living area is on the upper level. There is not ground-level living space, and there is an exterior staircase.
Small well-trained pet welcome! An additional deposit/cleaning fee,
Important Note: Garage is storage, not for parking guest automobiles.
Golf cart is not available for use.About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Traveler must engage in a conversation with the host about their group upon booking request..About checkIn:Check in after 4:30 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Select dates to view prices
10/10
1 reviewsHistoric Essex Home w/ Large Yard Near Downtown!
Hotel near Essex
The Historic Essex Home w/ Large Yard Near Downtown! is an ideal spot for travelers wanting to discover the city. The Historic Essex Home w/ Large Yard Near Downtown! is an ideal choice for travelers who want to take in the sights and sounds of Essex.
In terms of transportation, Madison is approximately 23km away. Traveling to and from the railway station is easy with Madison located approximately 23km away. There is no shortage of things to see in the area, with the Essex Indoor Golf Center, essex park and Essex Steam Train & Riverboat all nearby.
At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. This Essex hotel provides parking on site.
When it comes to Essex hotels, the Historic Essex Home w/ Large Yard Near Downtown! is highly regarded for its excellent facilities.
Select dates to view prices
10/10
2 reviewsDowntown Essex Apartment - Steps to River!
Hotel near Essex
The Downtown Essex Apartment - Steps to River! provides a great place for travelers to relax after a busy day. The Downtown Essex Apartment - Steps to River! is an ideal choice for travelers who want to take in the sights and sounds of Essex.
Madison is the closest major transportation option, approximately 24km away. The nearest railway station is Madison, approximately 24km away. There is no shortage of things to see in the area, with the Osage Trails, Pratt House Museum - Essex Historical Society and Essex Town all nearby.
When guests have some time on their hands they can make use of the onsite facilities. This Essex hotel offers parking on site.
When it comes to Essex hotels, the Downtown Essex Apartment - Steps to River! is highly regarded for its excellent facilities.
Select dates to view prices
FAQs About Middlesex County Hotels
What are the best places to stay in Middlesex County?
Some of the best places to stay in Middlesex County are near popular attractions like Saybrook Point Marina, offering easy access to key sights and amenities.
What are the top hotels in Middlesex County near Saybrook Point Marina?
Some of the top hotels in Middlesex County near Saybrook Point Marina include Saybrook Point Resort & Marina (from €323), Quality Inn Old Saybrook - Westbrook (from €85) and Liberty Inn Old Saybrook (from €77), all offering easy access to Saybrook Point Marina, making them ideal for visitors looking to explore the area.
Which hotels are the best hotels to stay at in Middlesex County?
Middlesex County has many popular hotels. Whether you're looking for a business stay or a vacation hotel, Postcard Cabins Machimoodus (from €176), Super 8 by Wyndham Cromwell/Middletown (from €53) and Inn at Middletown (from €154) are best choices.
What are the best hotels with a spa in Middlesex County?
Plan a peaceful trip? Spa can be a wonderful experience when traveling. Inn at Middletown (from €154), Copper Beech Inn (from €280) and Saybrook Point Resort & Marina (from €323) provide highly rated spa services.
What hotels in Middlesex County provide swimming pools?
Inn at Middletown (from €154), Courtyard Hartford Cromwell (from €182) and Saybrook Point Resort & Marina (from €323) are hotels with swimming pools. Book now and enjoy your swimming pool!
Which hotels in Middlesex County have the best breakfast?
Copper Beech Inn (from €280),Saybrook Point Resort & Marina (from €323) and Inn at Middletown (from €154) offer high-quality breakfast. Enjoy your wonderful journey with delicious breakfast!
What hotel deals are available in Middlesex County?
Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.
Middlesex County Hotels Info
Number of reviews
2,192
Total properties
55
Weekday Avg. Price
€215
Weekend Avg. Price
€255
Trending hotel
Postcard Cabins Machimoodus
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