Staypineapple, A Delightful Hotel, South End
Select date
-
Select date
1 night
Staypineapple, A Delightful Hotel, South End

Meet your Boston getaway: Staypineapple, A Delightful Hotel, South End. This 3-star standout has earned a 8.6/10 rating from 124 travelers, proving you don't have to compromise on quality for a great price, starting from $140.

Rooms

Deluxe King Room

Other

Deluxe King Room

Check-In & Check-Out

From 16:00 until 12:00

Nearby Attractions

Trinity Church: 0.53 km away

Boston | CamelPhat Concert: 0.54 km away

Boston | Sex Pistols 2026 Concert: 0.54 km away

Hotel Features

Dining & Drinks: Restaurant, Bar, Lobby bar

Staypineapple, A Delightful Hotel, South End

Show on map
We Price Match
Highlights
Bar
Ideal location
Pets welcome
Amenities
All amenities
Property Description
Show more
This hotel is cute! 
Surroundings
Commercial area: Downtown Boston
(1.0 mile)
Attraction: Chinatown
(600 ft)
Train station: Back Bay Station
(2050 ft)
Attraction: Boston Common
(2850 ft)
Attraction: Berklee College of Music
(4800 ft)
View on map
1

Deluxe King Room

1 King bed
Has window
Non-smoking
Air conditioning
Private toilet
Slippers
Desk
Room Details
Check Availability
10

Back Bay King

1 King bed
Non-smoking
TV
Video streaming services
Bedding: Down duvet
Bedding: Blanket or quilt
Room Details
Check Availability
8

South End Corner King

1 King bed
Non-smoking
Video streaming services
LCD TV
Bedding: Down duvet
Bedding: Blanket or quilt
Room Details
Check Availability

This property hasn't received any negative reviews in the past 10 months.
Average for similar properties in Boston
Guest User
May 13, 2026
Great location, safe neighborhood, clean and excellent service. The hotel is a bit old, but I'd definitely stay here again if I have the chance.
Original TextTranslation provided by AI
Guest User
April 18, 2026
Participated in a Boston field trip. There was a mix-up with my Revolution Hotel booking, and it got cancelled. However, the quick resolution and change of trip plans were excellent. Top-notch! And a big thank you to the Pineapple Hotel for their bar service!
Original TextTranslation provided by AI
Guest User
February 17, 2026
This hotel is cute! 
Guest User
May 18, 2026
Highly recommend, 10/10! 🏅 Staying at the Millennium Times Square New York for a couples' trip was an absolute dream! The location is unbeatable – just a few minutes' walk to Times Square, Broadway theaters, and Rockefeller Center. You step right out into the vibrant heart of New York, making it incredibly convenient for sightseeing and dining without rushing. Pure bliss! ✨ The cleanliness and attention to detail were top-notch. The room was spotless, and the floor-to-ceiling windows offered incredible views, whether it was the city skyline or the Hudson River; it was mesmerizing. Plus, the soundproofing was surprisingly good; we weren't bothered by any street noise or traffic, ensuring a peaceful night's sleep. 👍 Service was impeccable. The front desk staff were warm and attentive, even helping us plan our sightseeing routes. The food at the hotel's Beast & Butterflies restaurant was exquisite and delicious, and the rooftop terrace offered stunning panoramic views of Times Square at night – perfect for photos! 📸 Overall, it was a perfect experience for a couple. Finding such convenient and comfortable accommodation in pricey New York was truly the biggest surprise of our trip! I strongly recommend it to any couples visiting New York!
Original TextTranslation provided by AI
sofiia Shokhina
February 26, 2026
The hotel itself was clean, the bed was very comfortable, and the housekeeping staff was especially kind and attentive - we truly appreciated their work and hospitality. However, we experienced a serious issue regarding the resort fee policy, which left us feeling confused and misled as international guests. During online booking, the resort fee was listed as $25 per night, but important information about additional mandatory charges only appeared after payment was completed, when cancellation was no longer possible, wich is disappointing. Upon arrival, we were charged $200, which was later explained as $25 per person per night - something that was not clearly communicated during the booking process or at check-in. Initially, we believed this payment was a refundable deposit, as no clear explanation was provided. What felt particularly unacceptable was the way additional fees appeared in multiple stages: 1. extra charges becoming visible only after payment and confirmation, 2. additional payments required again upon arrival at the hotel, and 3. further unexplained charges after checkout - in our case, an additional $16 was withdrawn without clear justification. A staff member kindly explained that the resort fee includes Wi-Fi, water, and tea in the room, which we did use as they are standard services normally included in hotel stays worldwide. The fee also covered additional optional amenities such as bicycle parking and a complimentary alcoholic drink at the bar. However, we did not use these extra amenities, as they were not relevant to our stay. Since these services are optional by nature, it was unclear why guests are not given the choice to opt out instead of being required to pay for them regardless of usage. Even more concerning is that these mandatory resort fees are presented as payment for comfort and amenities, yet the overall stay did not fully reflect this. The soundproofing in the hotel is very poor, and we could clearly hear the neighbour’s television. The manual heating system in our room also did not function properly. We chose not to report these issues at the time because we spent little time in the hotel and did not expect the final cost of the stay to become so high. In hindsight, considering the total amount paid, these comfort issues become more significant. We strongly believe that all mandatory taxes and service fees should be transparently included in the total hotel price from the beginning. When fees continue to appear after payment, during check-in, and even after departure, guests understandably feel uncomfortable and misled. Because the final amount paid was much higher than expected, we realized that for the same total price we could have chosen a better hotel without additional hidden fees - which we in fact did for our following stay. We kindly ask the hotel to review these charges and consider a partial refund, as greater transparency and fairness in pricing would greatly improve trust and the overall guest experience
Guest User
April 25, 2026
Everything was amazing, our stay was very short but priceless. They borrow us bikes that we join to know as much as possible from the city, they offer us a spirit in the bar, and all of them are super easygoing and kind people!
Guest User
January 18, 2026
Location was central to Newbury St, Copley Square and not too far away to Boston Commons. Rooms were decent but the windows did not do much to keep the noise out. So you would be hearing a lot of noise that may disrupt your sleep. Toilet were a bit small so we'd need to balance out toiletries across various ledges and railings. Also, the window of our room was broken so we couldn't lift the window. The water pressure in the toilet were inconsistent. Front desk was helpful to hold our bags before and after check-in and the free drinks for the rooms were neat.
laozhanghehe2002
May 4, 2026
The room was clean, though a bit small. It was pretty quiet at night.
Original TextTranslation provided by AI
Guest User
April 22, 2025
Love it. I come here for Boston Marathon. It is so convenient that I walk like turtle after race and arrive the hotel within 15 minutes. I can rest and take a nap immediately after race.

Services & Amenities

Restaurant
No additional info available

Property Policies

Check-in and Check-out Times
Check-in: After 16:00
Check-out: Before 12:00

Front desk hours: 24/7

Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cribs and Extra Beds
For all room types, cribs cannot be added. Extra bed policies vary according to room type. Please refer to the relevant room type policy.

Pets
Pets are allowed on requestAdditional charge
Types of pets allowed: dogs
Fee: Contact the property for details

Service animals
Service animals are allowed on request

Age Requirements
The main guest checking in must be at least 18 years old

Paying at the hotel

  • Cash

Property Description

Local hotel name: Staypineapple, A Delightful Hotel, South End
  • Renovated: 2011
  • Number of Rooms: 56
Phone:+1-857-4446111
Email:INFO@STAYPINEAPPLE.COM

You might be wondering

What landmarks are near Staypineapple, A Delightful Hotel, South End?

Nearby attractions to Staypineapple, A Delightful Hotel, South End include Trinity Church, just 1750 ft from your search (straight-line distance) away.

Does Staypineapple, A Delightful Hotel, South End have a pool?

No, Staypineapple, A Delightful Hotel, South End doesn’t have a pool.

Does Staypineapple, A Delightful Hotel, South End serve breakfast?

No, Staypineapple, A Delightful Hotel, South End doesn’t serve breakfast.

Where is Staypineapple, A Delightful Hotel, South End located?

The hotel is located at 26 Chandler St.

Are pets allowed at Staypineapple, A Delightful Hotel, South End?

Yes, pets are welcome at Staypineapple, A Delightful Hotel, South End, but we suggest calling ahead to confirm details.

How much does it cost to stay at Staypineapple, A Delightful Hotel, South End?

Room rates at Staypineapple, A Delightful Hotel, South End vary based on dates, hotel policy, and other factors. Enter your travel dates to check current prices.

What are the check-in and check-out times at Staypineapple, A Delightful Hotel, South End?

Check-in at Staypineapple, A Delightful Hotel, South End starts at 16:00, and check-out is at 12:00.

About This Property

Nearest AirportBoston Logan International Airport
Distance to Airport8KM
Nearest Train StationBack Bay Station
Distance to Train Station0.59KM
Nearest Subway StationBack Bay
Distance to Subway Station0.61KM
Average Price FromUSD386
Hotel Star Rating3