Staypineapple, A Delightful Hotel, South End

Boutique hotel with restaurant, near Copley Square

Choose dates to view prices

Mon 8 Dec
Fri 12 Dec
December 2025
6
January 2026
Interior - Staypineapple, A Delightful Hotel, South End (Boston)
Reception - Staypineapple, A Delightful Hotel, South End (Boston)
Lobby sitting area - Staypineapple, A Delightful Hotel, South End (Boston)
Premium bedding, down duvets, pillow-top 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)
  • Restaurants 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
  • Lift
  • In-room climate control (air conditioning)
  • Premium bedding
£122
includes taxes & fees
4 Jan - 5 Jan 2026

Room options

Showing 2 of 2 rooms
Shower, designer toiletries, hair dryer, bathrobes
Premium bedding, down duvets, pillow-top beds, desk
Premium bedding, down duvets, pillow-top beds, desk
Premium bedding, down duvets, pillow-top beds, desk

South End Corner King

Excellent

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
Down duvet
Premium bedding
Designer toiletries
Hairdryer
  • Sleeps 2
  • 1 King Bed
Shower, designer toiletries, hair dryer, bathrobes
Premium bedding, down duvets, pillow-top beds, desk
Premium bedding, down duvets, pillow-top beds, desk
Premium bedding, down duvets, pillow-top beds, desk

Back Bay King

Wonderful

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
Down duvet
Premium bedding
Designer toiletries
Hairdryer
  • 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 a short 10-minute walk of Copley Square and Copley Place. For a bite to eat, guests can visit 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 travellers love the helpful staff and location. Public transportation is only 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

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 cots (infant beds)

Pets

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

Parking

    • No on-site 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 bike hire

Facilities

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

Accessibility

  • Lift
  • 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 duvet
  • Premium bedding
  • Pillow-top mattress

Freshen up

  • Private bathroom
  • Shower only
  • Designer toiletries
  • Hairdryer
  • Towels

Stay connected

  • Desk
  • Free local calls

Food and drink

  • Free bottled water

More

  • Housekeeping on request

Special features

Dining

Trophy Room – This restaurant specialises 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 checkout. 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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Guests can rest easy knowing that 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.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

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 that you 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 on-site 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 on-site 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. Travellers 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.

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

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

8/10 Very good

A fun, friendly and comfortable hotel

A quirky hotel in a great location. Our bed was really comfortable and the staff were very friendly. It was nice to be given a refillable bottle on arrival that could be topped up with icy cold still or sparkling water in reception, along with two vouchers for further drinks from the fridge in reception. We had a fantastic stay!
Jack, 4-night trip

10/10 Exceptional

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.
Emily, 4-night trip

10/10 Exceptional

Friendly Staff

Both the staff at the hotel and the Trophy Room restaurant were absolutely amazing!! Beds were very comfortable and we liked the location
Holly, 3-night trip

8/10 Very good

Great staff and great location, convenient to trains and subway. Fun bar in the lobby connected to the hotel. Very comfy beds.
Karen, 3-night trip

10/10 Exceptional

It’s in a nice location and the hotel is really cute. Severe able to walk to our event at the Wang and felt safe. The staff was very nice and there was a cute dog in residence.
Brigid, 1-night trip

10/10 Exceptional

This hotel is so cute! It was a great location to everything!
Caitlin, 3-night trip

6/10 Good

Most of the staff was great, especially Cynthia! It would be great if there was food available more than between the hours of 4-11. The bar staff could also be a bit kinder to women who are staying in the hotel. Everyone was great with my dog but the communication was pretty poor. I was told that I was booked through Thursday night by one person and then had to scramble for somewhere to stay on my last night in town with less than an hour notice. The person who told me this wasn’t very kind and i got locked out of my room while my dog was in there. There was no one at the desk and it was all very stressful. Overall, it was okay but I would stay somewhere else next time.
Jill, 5-night trip

10/10 Exceptional

Food is great here... Rooms are super cute.
Cyndie, 6-night trip

10/10 Exceptional

had a wonderful experience. Very cozy and comfortable love the ambience like The Restaurant was attached to it totally recommend.
Carrie, 4-night trip

10/10 Exceptional

Friendly, knowledgeable and accommodating staff. A very cute room!!
Jill, 3-night trip

10/10 Exceptional

Very quaint, fun hotel. Staff was very friendly, accomodating, and helpful. The room was compact, but comfortable, very European design. The pineapple theme throughout was fantastic. The towels, linens, etc were great quality. I would definitely stay again.
Shannon, 2-night trip

8/10 Very good

The rooms are small, but very clean and comfortable.
Brian, 1-night trip

10/10 Exceptional

Very kind staff. Awesome bar connected and great food. Would stay again!
Helen, 1-night trip

8/10 Very good

Great time in the south end

We had a great stay at Staypineapple Boston! The staff was truly amazing—friendly, helpful, and made us feel very welcome. The location is fantastic, perfect for exploring the city. A couple of small issues like holes in the blinds and some city noise at night, but overall, a really enjoyable experience.
Brett, 4-night trip

10/10 Exceptional

Loved this quirky boutique hotel. It has great character, very clean, great walkable location. In south end - convenient to shopping and Fenway!
Linda, 1-night trip

10/10 Exceptional

Absolutely amazing bedding - very comfortable! We will definitely stay again - very walkable to the Boston Commons, shopping, restaurants and theater. Staff were very nice and personable. A wonderful stay.
Barbara, 2-night trip

10/10 Exceptional

Great location, friendly staff, and comfortable rooms. Yes, the rooms are smaller than average, but only if you're expecting American-style hotel rooms (which waste a lot of space). It was plenty spacious, and very comfortable.
Ryan, 4-night trip

8/10 Very good

Rooms are small. People are nice .
Justin, 3-night trip

10/10 Exceptional

Loved the decor and the bikes to ride around the city!
Andrea, 1-night trip

10/10 Exceptional

Great hotel with a good location..Every staff member provided us and amazing service ;)))