See all properties

Staypineapple, A Delightful Hotel, South End

3.0 star property

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Lobby sitting area
Bar (on property)
Premium bedding, down comforters, pillowtop beds, desk
Reception

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk
The current price is $179
includes taxes & fees
Jun 7 - Jun 8

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Square
    ‪6 min walk‬
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Boston Common
    ‪10 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪6 min drive‬

Room options

View all photos for South End Corner King

Premium bedding, down comforters, pillowtop beds, desk

South End Corner King

8.8 out of 10
Excellent
(9 reviews)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.2 out of 10
Wonderful
(51 reviews)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

Similar properties

Lobby sitting area
The Revolution Hotel
South End
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 2,623 reviews
The Revolution Hotel

About this property

Staypineapple, A Delightful Hotel, South End

3-star hotel in South End
This smoke-free hotel features a restaurant, a bar/lounge, and coffee/tea in a common area. Additionally, free use of bicycles, concierge services, and a 24-hour front desk are onsite. Housekeeping is available on request.
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with complimentary bottled water and coffee/tea makers. Pillowtop beds feature down comforters and premium bedding. 50-inch flat-screen televisions come with satellite channels.

Bathrooms include showers, bathrobes, designer toiletries, and complimentary toiletries. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided on request.

Recreational amenities at the hotel include complimentary bicycles.
The hotel offers a restaurant. A bar/lounge is on site where guests can unwind with a drink. This business-friendly hotel also offers multilingual staff, tour/ticket assistance, and coffee/tea in a common area.

Staypineapple, A Delightful Hotel, South End is a smoke-free property.

Trophy Room - This restaurant specializes in American cuisine and serves brunch and dinner. Guests can enjoy drinks at the bar.

Property amenities

Internet

  • Available in all rooms: Free internet

Parking and transportation

  • No onsite parking available

Food and drink

  • A bar/lounge
  • A restaurant
  • Coffee and tea in common areas

Restaurants on site

  • Trophy Room

Things to do

  • Free bicycle rentals

Conveniences

  • 24-hour front desk
  • Luggage storage
  • Water dispenser

Guest services

  • Concierge services
  • Housekeeping (on request)
  • Multilingual staff
  • Tour and ticket assistance

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Elevator
  • Hardwood flooring in room
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk
  • Wheelchair-accessible restaurant

More

  • 1 building
  • 8 floors
  • Built in 1900
  • Fireplace in lobby
  • No plastic water bottles
  • Smoking not allowed
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Down comforter
  • Hypo-allergenic bedding
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 50-inch flat-screen TV with cable/satellite channels
  • iPod dock
  • Streaming services

Food and drink

  • Coffee/tea maker
  • Free bottled water

More

  • Air conditioning (climate-controlled)
  • Desk
  • Free local calls
  • Heating (climate-controlled)
  • Iron/ironing board on request
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4 PM; Check-in end time: midnight
Minimum check-in age: 18

Check-out

Check-out before noon
Contactless check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 29.95 per pet, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Specific rooms only, restrictions apply; pet-friendly rooms can be requested by contacting the property at the number on the booking confirmation
Food and water bowls are available

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 29.06 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • In-room bottled water
  • In-room coffee
  • Internet access
  • Sporting facilities or equipment

We have included all charges provided to us by the property.

Optional extras

  • Pet fee: USD 29.95 per pet, per night
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Tax ID - C0014880350
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a smoke detector
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property

We should mention

This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

Property is also known as

Chandler Inn Hotel Boston
Chandler Boston
Staypineapple A Delightful Hotel South End
"Staypineapple A Delightful Hotel South End"
Staypineapple, A Delightful Hotel, South End Hotel
Staypineapple, A Delightful Hotel, South End Boston
Staypineapple, A Delightful Hotel, South End Hotel Boston

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 646 out of 1000 reviews
Rating 8 - Good. 226 out of 1000 reviews
Rating 6 - Okay. 71 out of 1000 reviews
Rating 4 - Poor. 31 out of 1000 reviews
Rating 2 - Terrible. 26 out of 1000 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.8/10

Property conditions & facilities

Reviews

6/10 Okay

moonshine

Liked: Cleanliness, amenities, property conditions & facilities
There’s doesn’t seem to be any soundproofing I got stuck with noisy neighbors unfortunately otherwise the front desk staff was very friendly and informative
Stayed 2 nights in Feb 2026

8/10 Good

daniel

Stayed 1 night in Feb 2026

10/10 Excellent

Morgan

Stayed 2 nights in Feb 2026

6/10 Okay

Jeanne

Traveled with pets
Liked: Cleanliness
Disliked: Amenities
The bed was hard, the front desk makes no sense and was very awkward to use. The room was clean but you could hear the music from the bar upstairs on the second floor. It was just an ok place, I booked it based on the reviews and I can agree with it being clean but that's pretty m much it really. I also did NOT appreciate the stuffed dog in the bed, my dog immediately went right for it and I had to pay $30 for an over priced stuffed dog that clearly was worth only $10 at the most. They should or those stuffed animals where a dog cannot get to it and allow the visit to decide whether or not to buy it. I felt it was a very sneaky move on their end and again I didn't appreciate it at all. The good at the restaurant was really good, but I will not be staying here again based on the comfort level, the stuffed animal situation and the rooms are super tiny.
Stayed 1 night in Feb 2026

10/10 Excellent

Rod

Liked: Cleanliness, staff & service, amenities
Yes it was spotless and well organized.
Stayed 1 night in Jan 2026

10/10 Excellent

Kenneth

Stayed 1 night in Feb 2026

10/10 Excellent

Tevin

Stayed 1 night in Feb 2026

10/10 Excellent

Simeng

Liked: Cleanliness, property conditions & facilities
the staff is excellent!
Stayed 3 nights in Feb 2026

10/10 Excellent

Christopher

Stayed 1 night in Feb 2026

10/10 Excellent

kevin

Stayed 3 nights in Feb 2026

8/10 Good

Karen

Liked: Cleanliness, staff & service, amenities
Great location cute bar. Room small but good use of space
Stayed 1 night in Feb 2026

6/10 Okay

Jesse, New York

Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
Charged a $29 amenity fee that was not disclosed when I checked in. Heat was on way too high with no way to control it. The bathroom sink is tiny. I also did not appreciate when the man who checked me in made a remark how my name sounded like a martial arts movie star (I’m Chinese). I come to Boston frequently and have stayed at many local hotels and would not stay here again.
Stayed 1 night in Feb 2026

10/10 Excellent

Joy

Liked: Cleanliness, amenities, property conditions & facilities
Loved this hotel. Convenient to everything, nice staff , rooms had everything you could need and the bed was very cozy. Loved the free reusable water bottle and the complimentary cocktail at the bar . Highly recommend
Stayed 2 nights in Feb 2026

10/10 Excellent

Rebecca

Stayed 1 night in Feb 2026

10/10 Excellent

Kenneth

Stayed 1 night in Feb 2026

8/10 Good

Mikita

Liked: Cleanliness, amenities, property conditions & facilities
Room was spotless but would be nice if they offer extra bottles of water
Stayed 5 nights in Jan 2026

10/10 Excellent

Hortencia

Liked: Cleanliness, staff & service, amenities
Clean and great location. Wonderful service. Really enjoyed our stay and will return.
Stayed 3 nights in Nov 2025

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities
The cleanliness of the entire property was above average, the friendliness was fantastic
Stayed 1 night in Feb 2026

10/10 Excellent

Jillian

Stayed 2 nights in Jan 2026

10/10 Excellent

Skyler

Liked: Cleanliness, amenities, property conditions & facilities
Everyone was very kind and accommodating! Rooms were so cozy and clean. Would definitely stay again.
Stayed 1 night in Jan 2026

10/10 Excellent

Fernando

Wonderful stay
Stayed 1 night in Jan 2026

10/10 Excellent

Faigy

Stayed 3 nights in Jan 2026

10/10 Excellent

Chantel, Bronx

Stayed 1 night in Jan 2026

10/10 Excellent

Geraldine

Stayed 1 night in Jan 2026

10/10 Excellent

Aimee

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Super cute room staff was great
Stayed 1 night in Jan 2026