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Staypineapple, A Delightful Hotel, South End

3.0 star property

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Photo gallery for Staypineapple, A Delightful Hotel, South End

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

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk
$122
includes taxes & fees
Jan 19 - Jan 20, 2026

Explore the area

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

Room options

View all photos for South End Corner King

Premium bedding, down comforters, pillowtop beds, desk

South End Corner King

8.6 out of 10
Excellent
(8 reviews)
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.0 out of 10
Wonderful
(46 reviews)
  • Sleeps 2
  • 1 King Bed

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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 iPod docking stations and complimentary bottled water. 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). Additionally, rooms include coffee/tea makers and hair dryers. 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
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk

More

  • 1 building
  • 8 floors
  • Built in 1900
  • 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
  • Shower
  • 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. 618 out of 1001 reviews
Rating 8 - Good. 253 out of 1001 reviews
Rating 6 - Okay. 72 out of 1001 reviews
Rating 4 - Poor. 34 out of 1001 reviews
Rating 2 - Terrible. 24 out of 1001 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

10/10 Excellent

dana

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Sep 2025

6/10 Okay

Robert

Stayed 2 nights in Sep 2025

8/10 Good

Shaun

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Quirky little Hotel in a quiet residential area of South End. Reception staff were excellent, room was decked out in the Pineapple theme - very good. Bar on site - good but only used it once as we were here to explore. Back Bay T Station is 5 min walk & 3 stops to centre of Boston. I would recommend this hotel to anyone & everyone.
Stayed 5 nights in Sep 2025

10/10 Excellent

michelle

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this hotel!! Room only, very comfy bed and bedding - 2 duvets so you no longer have to fight for your half….. genius!!! Loved all of the little extras, silky robes, coffee maker with tea pods (I’m a tea drinker and so many places only supply coffee) free metal water bottle and fresh/chilled/gas water machine in the reception alongside free coffee all day. In the Back Bay Area which is super lovely and we walked from here into Boston which was about 20 mins and also back from Fenway Park after a game which was about 30-40 mins but was very safe. Also very close to the Avis/Budget garage when you need to collect the hire car!! Would highly recommend!
Stayed 3 nights in Sep 2025

10/10 Excellent

Jane E

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

10/10 Excellent

Tami

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
No photos sorry
Stayed 1 night in Sep 2025

8/10 Good

jacqueline

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Mitchell and Silvia were so extraordinary helpful nothing was too much trouble. The position was central and the rooms were fun ( touch of pineapples) and clean. Would highly recommend it as a less expensive place to stay
Stayed 3 nights in Sep 2025

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Sep 2025

10/10 Excellent

Jennifer

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Had everything we needed?
Stayed 3 nights in Sep 2025

2/10 Terrible

Richard

Traveled with partner
Disliked: Staff & service, amenities, property conditions & facilities
Hotel priced like a five star but rooms were the size of a closet with limited housekeeping. Our room was 60 degrees - freezing! When we asked for help to make the room warmer we were told management did not plan to turn the heat on for another week. They brought us a space heater that was loud and dangerous. We turned it off and nearly froze to death. We will never come back here at any price. Beware - the front desk did not have any concerns about our satisfaction.
Stayed 2 nights in Sep 2025

8/10 Good

steven louis

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent staff, incredible location for walking around town.
Stayed 3 nights in Sep 2025

8/10 Good

Christopher

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Sep 2025

6/10 Okay

Curtis

Traveled with family
Liked: Cleanliness, staff & service
Disliked: Amenities
Nice location. Rooms had no microwave or refrigerator. Leaky toilet was very loud, had to turn off water after each use. AC ran until too cold, needs thermostat adjustment.
Stayed 3 nights in Sep 2025

10/10 Excellent

Teresa

Stayed 1 night in Sep 2025

10/10 Excellent

Ashley

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The perfect location! Super comfy beds.
Stayed 2 nights in Sep 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
Very interesting hotel, very quiky but lovely room. Very clean. Awesome, helpful staff. Would highly recommend
Stayed 1 night in Sep 2025

10/10 Excellent

Hunter

Stayed 3 nights in Aug 2025

10/10 Excellent

Oliver

Stayed 1 night in Sep 2025

10/10 Excellent

Randall

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Enjoyed the onsite bar and other amenities. Room was comfortable. Bathroom was very tiny, but manageable. Very walkable to shopping and dining options. Decor was very nice. Would recommend.
Stayed 4 nights in Sep 2025

10/10 Excellent

Scott

Liked: Cleanliness, staff & service
Stayed 4 nights in Sep 2025

10/10 Excellent

Jeff

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

10/10 Excellent

Rebecca

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very unique. Truly delightful experience!
Stayed 2 nights in Aug 2025

10/10 Excellent

Marybeth

Liked: Cleanliness, staff & service, property conditions & facilities
Room was cozy
Stayed 2 nights in Aug 2025

8/10 Good

James

Liked: Cleanliness, staff & service
Disliked: Amenities, property conditions & facilities
Tiny toilet
Stayed 4 nights in Sep 2025

10/10 Excellent

Emily

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property was in such a great area and walkable distance to many sights in Boston. I traveled for a birthday and they accommodated decorations free of charge. The staff were on site late into the night and available to help. Room was comfortable and the Trophy Room restaurant on the bottom floor was nice and LGBTQ+ friendly.
Stayed 4 nights in Aug 2025