Kent County

Kent County Homestays

Book Homestays Kent County for local life and cozy charm.

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Popular Homestays in Kent County

Book Kent County Homestays for authentic vibes.
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Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Kent County
When you stay at Inn at Huntingfield Creek in Rock Hall, you'll be on the waterfront, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. This spa bed & breakfast is 1.7 mi (2.8 km) from The Mainstay and 2.2 mi (3.5 km) from Rock Hall Harbor. Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area. A complimentary local cuisine breakfast is served daily from 8:30 AM to 9:00 AM. Free self parking is available onsite. Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.
Outstanding
58 reviews
9.8/10
1 night
From $161
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76
Hotels in Kent County
Featured facilities: Clothes dryer, Parking
Good
48 reviews
7.8/10
1 night
From $132
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28
Hotels in Kent County
Featured facilities: Kitchen, Washing machine
Outstanding
20 reviews
10/10
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24
Hotels in Kent County
Featured facilities: Clothes dryer
Outstanding
10/10
Check availability
26
Hotels in Kent County
Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round. Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.During your stay you will have exclusive access to the following rooms and spaces:- Bedroom- Full bathroom- Kitchenette- Living room- Dining area- PatioAdditionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.Here's what some of our recent guests have said about their stay:"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - CarlaWe're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you. Book now to secure your spot!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.While not child friendly, we can accommodate..About customRules:There is a maximum stay of one month for Instant Bookings. For longer stays, please message the host first. Otherwise, your booking may be cancelled..The max number of guests is two people. If you are two adults traveling with a child under 5, we can accommodate but you must let us know at booking..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
45 reviews
10/10
Check availability
10
Hotels in Kent County
Lovely bayside Bungalow on a quiet street on Swan Creek with an indoor dry Swedish sauna and views of the cheseapeake Bay.Private entrance. Bikes and beach chairs provided. Microwave and small refrigeratorAbout 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 events:No events allowed.
Outstanding
45 reviews
10/10
Check availability
14
Hotels in Kent County
Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liquor store and grocery.We are a 15-minute ride to Chestertown, home of Washington College and host to wonderful restaurants, lovely shops, galleries and more!The spaceYour suite will be clean and ready for your arrival with everything you need for a comfortable stay. WIFI is included and information on the area will be in your room. Fresh ice, water, coffee, tea and snacks will also be provided. You will also have access to a lounge, which is a comfortable place to read a book, have a conversation or watch TV.Guest accessYou have your bedroom and bathroom to yourself. The lounge is shared. Please note, the bedroom suite is on the second floor. Access is by stairs.During your staySomeone will be available in person or by phone or text to answer any questions you have about the house or area. Your separate entrance opens digitally and is changed with each new occupant, so you will be able to come and go independently.We include a few snacks, water and self-service breakfast items plus coffee, tea, etc. Unlike a B and B, this is self-service and you may even use the microwave to heat things. There is also a small refrigerator in the suite. If you need something that is not provided in the list, please ask. We will do whatever we can, within reason, to accommodate.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.
Amazing
9.6/10
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22
Hotels in Kent County
Featured facilities: Kitchen, Washing machine
Outstanding
8 reviews
10/10
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16
Hotels in Kent County
Featured facilities: Washing machine
Amazing
67 reviews
9.6/10
Check availability
34
Hotels in Kent County
Featured facilities: Kitchen, Washing machine
Outstanding
13 reviews
9.8/10
Check availability
See More Homestays in Kent County

Frequently Asked Questions

What are some of the best Homestays in Kent County?

Whether you are traveling to Kent County for business or tourism, The Lodge at Great Oak Landing (from $137) and Inn at Huntingfield Creek (from $178) are good options.

How much for staying Homestays in Kent County?

For Homestays in Kent County, the average price is $294 on weekdays, and $352 on weekends (Friday–Saturday).

Do any Homestays in Kent County have a pool?

Want to enjoy a swimming pool during your trip? There are many Homestays in Kent County with a pool. The Lodge at Great Oak Landing (from $137) and Inn at Huntingfield Creek (from $178) are very popular.

Which Homestays in Kent County offer a gym?

Among Homestays in Kent County, The Lodge at Great Oak Landing (from $137) has great fitness facilities.

Do any Homestays in Kent County offer breakfast?

Inn at Huntingfield Creek (from $178) provides high-quality breakfast.

Which Homestays in Kent County provide parking spaces?

Kent County Homestays Information

Total properties12
Number of reviews212
Weekend Avg. Price$352
Weekday Avg. Price$294