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Staypineapple, A Delightful Hotel, South End

Boutique hotel with restaurant, near Copley Square

Choose dates to view prices

Sun, Dec 7
Wed, Dec 10
December 2025
5
January 2026
Interior - Staypineapple, A Delightful Hotel, South End (Boston)
Lobby sitting area - Staypineapple, A Delightful Hotel, South End (Boston)
Reception - Staypineapple, A Delightful Hotel, South End (Boston)
Premium bedding, down comforters, pillowtop beds, desk - Staypineapple, A Delightful Hotel, South End (Boston)
Bar (on property) - Staypineapple, A Delightful Hotel, South End (Boston)
In the heart of South End, Staypineapple, A Delightful Hotel, South End offers a haven of relaxation. With a bar and restaurant on site, you can unwind with your favorite drink or meal. Explore the nearby Copley Place and Newbury Street on two wheels with free bicycle rentals or get insider tips from the multilingual staff.
VIP Access
Wonderful

Popular amenities

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

Main amenities (10)

  • Housekeeping (on request)
  • Restaurant and bar/lounge
  • Free use of bicycles
  • 24-hour front desk
  • Coffee/tea in a common area
  • Water dispenser
  • Multilingual staff
  • Concierge services
  • Luggage storage
  • Tour/ticket assistance

Feel at home (6)

  • Private bathroom
  • Cable/satellite TV service
  • Coffee/tea maker
  • Elevator
  • In-room climate control (air conditioning)
  • Premium bedding
CA $149
CA $215 total
includes taxes & fees
Dec 17 - Dec 18

Room options

Showing 2 of 2 rooms
Shower, designer toiletries, hair dryer, bathrobes
Premium bedding, down comforters, pillowtop beds, desk
Premium bedding, down comforters, pillowtop beds, desk
Premium bedding, down comforters, pillowtop beds, desk

South End Corner King

Excellent

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
Down duvet
Premium bedding
Designer toiletries
Hair dryer
  • Sleeps 2
  • 1 King Bed
Shower, designer toiletries, hair dryer, bathrobes
Premium bedding, down comforters, pillowtop beds, desk
Premium bedding, down comforters, pillowtop beds, desk
Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

Wonderful

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
Down duvet
Premium bedding
Designer toiletries
Hair dryer
  • Sleeps 2
  • 1 King Bed

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About the area

Map
26 Chandler St, Boston, MA, 02116

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

  • Logan International Airport (BOS) - 7 min drive
  • Boston, MA (BNH-Boston Harbor Seaplane Base) - 17 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 33 min drive
  • Norwood, MA (OWD-Norwood Memorial) - 35 min drive
  • Bedford, MA (BED-Laurence G. Hanscom Field) - 35 min drive
  • Lawrence, MA (LWM-Lawrence Municipal) - 36 min drive
  • Portsmouth, NH (PSM-Portsmouth Intl.) - 72 min drive
  • Back Bay Station - 6 min walk
  • South Station - 21 min walk
  • Boston Ruggles Station - 25 min walk
  • Arlington Station - 8 min walk
  • Tufts Medical Center Station - 9 min walk
  • Copley Station - 10 min walk

Restaurants

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

About this property

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End offers a great location, putting you within just a 10-minute walk of Copley Square and Copley Place. For a bite to eat, guests can check out Trophy Room, which serves American cuisine and is open for dinner. Other highlights at this boutique hotel include a bar/lounge and free bike rentals. Fellow travelers love the helpful staff and location. Public transportation is just a short walk: Arlington Station is 8 minutes and Tufts Medical Center Station is 9 minutes.

At a glance

Hotel size

    • 56 rooms
    • Arranged over 8 floors

Arriving/Leaving

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

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 18

Children

    • No cribs (infant beds)

Pets

    • Pets allowed (dogs only, 2 total)*
    • Service animals welcome
    • Specific rooms only, restrictions apply*
    • Food and water bowls available

Parking

    • No onsite parking

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Restaurant
  • Bar/lounge
  • Coffee/tea in a common area
  • Water dispenser

Services

  • 24-hour front desk
  • Concierge services
  • Tour/ticket assistance
  • Luggage storage
  • Multilingual staff
  • Free bicycle rentals

Facilities

  • 1 building/tower
  • Built in 1900
  • No plastic water bottles
  • Water dispenser

Accessibility

  • Elevator
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible registration desk

Room amenities

Be entertained

  • 50-inch flat-screen TV
  • Satellite TV channels
  • Streaming services

Home comfort

  • Climate-controlled air conditioning and heating
  • Coffee/tea maker
  • Bathrobes
  • Iron/ironing board (on request)

Sleep well

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

Freshen up

  • Private bathroom
  • Shower only
  • Designer toiletries
  • Hair dryer
  • Towels

Stay connected

  • Desk
  • Free local calls

Food and drink

  • Free bottled water

More

  • Housekeeping on request

Special features

Dining

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

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or check-out. Fees may include applicable taxes:
  • Resort fee: USD 29.06 per accommodation, per night
  • Resort fee inclusions:
    • Additional inclusions
    • In-room bottled water
    • In-room coffee
    • Internet access (may be limited)
    • Sporting facilities or equipment

Pets

  • Service animals exempt from fees
  • Pets are allowed for an extra charge of USD 29.95 per pet, per night

Policies

Guests can rest easy knowing there's a smoke detector on site.
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover, Diners Club, Union Pay
Cashless transactions are available.
State tax ID - C0014880350
Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.

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

Frequently asked questions

Does Staypineapple, A Delightful Hotel, South End offer free cancellation for a full refund?

Yes, Staypineapple, A Delightful Hotel, South End does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

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

Yes, dogs are welcome, with a limit of 2 total. There's a charge of USD 29.95 per pet, per night. Service animals are exempt from fees. Food and water bowls are available. Some restrictions may apply, so please contact the property for more details.

Is parking offered on site at Staypineapple, A Delightful Hotel, South End?

Sorry, there's no onsite parking at Staypineapple, A Delightful Hotel, South End.

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

Check-in start time: 4 PM; Check-in end time: midnight. Check-out time is noon. Contactless check-out is available.

Is there an onsite casino at Staypineapple, A Delightful Hotel, South End?

No, this hotel doesn't have a casino, but Encore Boston Harbor (9-min drive) is nearby.

What is there to do at Staypineapple, A Delightful Hotel, South End and nearby?

Have fun during the warmer months with activities such as cycling.

Are there restaurants at or near Staypineapple, A Delightful Hotel, South End?

Yes, Trophy Room offers American cuisine.

What's the area around Staypineapple, A Delightful Hotel, South End like?

Staypineapple, A Delightful Hotel, South End is in South End, a short 7-minute drive from Logan International Airport (BOS) and 9 minutes' walk from Copley Square. Travelers say that the hotel is in a great location.

Have a question?

Get instant answers with AI powered search of property information and reviews.

Staypineapple, A Delightful Hotel, South End Reviews

9.0

Wonderful

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Popular mentions

RoomService staffLocationBedRestaurantBarBathroomShowerParkingAmenities

What guests liked

  • The property's restaurant and nearby dining options were highly praised for their quality, variety, and convenience. (10 reviews)
  • The property has a welcoming and dog-friendly atmosphere with helpful staff and accessible pet access. (3 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

8/10 Very good

Really cute hotel and good restaurant. On a cool Boston night room was warm and comforting. Enjoyed our visit Would go back again.
Rod, 1-night trip

10/10 Exceptional

Nice little hotel located in Back Bay. Friendly staff and nicely decorated rooms
JEAN-CHRISTOPHE, 3-night trip

10/10 Exceptional

Wonderful staff service! Appreciated the amenities and super cute aesthetic of the property.
Susan, 1-night trip

10/10 Exceptional

Great area & hotel

Loved the hotel, gay friendly area as well. Super cute, will stay again!
2-night trip

10/10 Exceptional

This is a great little hotel.
Gayle, 4-night trip

10/10 Exceptional

Great location
Clelia Maria, 5-night trip

10/10 Exceptional

We really enjoyed the stay here. Very clean, friendly staff, good location. Highly recommend.
Nick, 4-night trip

10/10 Exceptional

Just thought was excellent location.
Derek, 2-night trip

8/10 Very good

The staff was nice
Hailey, 3-night trip

8/10 Very good

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
jacqueline, 3-night trip

8/10 Very good

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.
Shaun, 5-night trip

10/10 Exceptional

Room was small but felt so good. Room was clean and staff was super friendly
David, 2-night trip

10/10 Exceptional

Great location hotel with great atmosphere

The room was...cozy. The hotel was had a great atmosphere, comfortable bed, and was walking distance to many restaurants and sights. Would highly recommend.
Francis, 2-night trip

10/10 Exceptional

Friendly staff
Giovanna, 3-night trip

10/10 Exceptional

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
Nick, 1-night trip

8/10 Very good

nice place to stay but the bedding was odd
Michael, 2-night trip

10/10 Exceptional

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.
Taylor, 1-night trip

10/10 Exceptional

Loved this property. A lot of detail has gone into the decor. Staff very welcoming.
Tim, 2-night trip

10/10 Exceptional

Room was nice and clean. In a nice and safe location.
Jonathan, 3-night trip

8/10 Very good

Great option within walking distance to downtown
Walter, 3-night trip

8/10 Very good

This is very cute hotel nestled in a quiet residential area next to everything.
Fullando, 3-night trip

10/10 Exceptional

Great value for the price
Rajesh, 2-night trip

10/10 Exceptional

We loved our stay here! The hotel is great & the bar was super fun! The location was great, an easy walk to wherever you want go!
Melissa, 2-night trip

10/10 Exceptional

Worked out really well from 3 days in Boston
Mark, 3-night trip

10/10 Exceptional

Super cute boutique hotel, staff were incredibly friendly and helpful. Rooms were small but cozy, the separate duvets were a great touch. Would definitely return!
Laura, 3-night trip