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Staypineapple, A Delightful Hotel, South End

3.0 star property

Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Premium bedding, down duvets, pillow-top beds, desk
Reception
Bar (on property)
Lobby sitting area

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air-conditioning
  • Bar
  • 24/7 front desk

Explore the area

View 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 duvets, pillow-top 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 duvets, pillow-top beds, desk

Back Bay King

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

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About the area

Boston

With a stay at Staypineapple, A Delightful Hotel, South End, you'll be centrally located in Boston, a 9-minute walk from Copley Square and 13 minutes by foot from Boston Common. .This boutique hotel is 1.7 mi (2.7 km) from New England Aquarium and 1.9 mi (3.1 km) from TD Garden.

What's nearby

  • Copley Place - 6 min walk - 0.6 km
  • Newbury Street - 8 min walk - 0.7 km
  • Copley Square - 8 min walk - 0.7 km
  • The Shops at Prudential Center - 10 min walk - 0.9 km
  • Boston Common - 13 min walk - 1.1 km

Getting around

  • Back Bay Station - 6 min walk
  • Arlington Station - 8 min walk
  • Boston, MA (BNH-Boston Harbor Seaplane Base) - 17 min drive

Restaurants

  • ‪Club Café - ‬3 min walk
  • ‪The Friendly Toast - ‬4 min walk
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪Trophy Room - ‬1 min walk
  • ‪Berkeley Perk Cafe - ‬1 min walk

About this property

Staypineapple, A Delightful Hotel, South End

Hotel with a restaurant, 9-minute walk to Copley Square
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.
Make yourself at home in one of the 56 guestrooms featuring iPod docking stations and flat-screen televisions. Your pillowtop bed comes with down comforters and premium bedding. Satellite television is provided for your entertainment. Private bathrooms with showers feature designer toiletries and hair dryers.
This smoke-free hotel features complimentary bicycles on site.
Enjoy a satisfying meal at Trophy Room serving guests of Staypineapple, A Delightful Hotel, South End. Quench your thirst with your favorite drink at the bar/lounge.
Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage.
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 transport

  • No on-site 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.
  • Lift
  • 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
  • Smoke-free property
  • Water dispenser usage encouraged

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Dressing gowns
  • 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

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 1003 reviews
Rating 8 - Good. 253 out of 1003 reviews
Rating 6 - Okay. 73 out of 1003 reviews
Rating 4 - Poor. 35 out of 1003 reviews
Rating 2 - Terrible. 24 out of 1003 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

Tami

Travelled 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

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

2/10 Terrible

Richard

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great area & hotel

Loved the hotel, gay friendly area as well. Super cute, will stay again!
Stayed 2 nights in Aug 2025

10/10 Excellent

Michael, Washington

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Aug 2025

6/10 Okay

shelley, Newport Beach

Liked: Cleanliness, staff & service
Disliked: Amenities
Rooms are very small, restaurant bar was just below our room and open til 1am-very loud, restaurant for breakfast has very limited menu and coffee is terrible.
Stayed 1 night in Aug 2025

4/10 Poor

Tico

Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
The guest “amenity” charge is outrageous, especially at $24.95 per day. I used no amenities aside from the one water bottle that states it’s complimentary on the tag and the three coffee pods that were provided. I didn’t have housekeeping come into my room, so nothing was replenished, so what exactly am I being charged for at such a rate times three? What amenities? Quite frankly, $24.95 a day is exorbitant for what is "provided." And especially when all I had is the water and three coffee pods for all three days/nights. I would much rather pay for what I actually use than be charged for what I don't under the guise of friendly service/convenience. But it is what it is. Now I know not to stay at another one of thrse locations during my next travels. Very disappointing. Because I did like the hotel, but what I don't like is the pretense of"pineappley" service when it's just blatant highway robbery.
Stayed 3 nights in Aug 2025

8/10 Good

maria elena sanchez

Liked: Cleanliness
Stayed 2 nights in Jul 2025