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

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • 24/7 front desk
  • Bar
  • Air conditioning
$122
includes taxes & fees
Jan 4 - Jan 5, 2026

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Place
    ‪6 min walk‬
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Copley Square
    ‪8 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. 617 out of 1002 reviews
Rating 8 - Good. 253 out of 1002 reviews
Rating 6 - Okay. 73 out of 1002 reviews
Rating 4 - Poor. 35 out of 1002 reviews
Rating 2 - Terrible. 24 out of 1002 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

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

10/10 Excellent

Verified traveler

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

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic spot for the price, it was super clean and cute! Only downside is no parking, but there was plenty of spots near it to park at. 10/10 experience and staff was super nice
Stayed 1 night in Aug 2025

8/10 Good

Candice

Business traveler
Liked: Staff & service
Stayed 4 nights in Aug 2025

8/10 Good

Hailey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was nice
Stayed 3 nights in Aug 2025

6/10 Okay

james

Liked: Cleanliness, staff & service, room comfort
Stayed 3 nights in Jul 2025

10/10 Excellent

Scott

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

10/10 Excellent

Taylor

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

What a fun, lovely, independent hotel.

What a cute hotel! Great location, clean rooms, love all the attention to details, plus the free reusable water bottle is amazing! Omg and the bed is SO COMFY. I would stay here in a heartbeat, and actually added another night at the hotel instead of staying with friends it’s that good.
Stayed 1 night in Aug 2025

10/10 Excellent

Ryan

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