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Staypineapple, A Delightful Hotel, South End

City-center hotel within easy reach of Copley Square

  • Free WiFi

Image gallery

  • Staypineapple, A Delightful Hotel, South End
  • Staypineapple, A Delightful Hotel, South End
  • South End Corner King - Bathroom
  • South End Corner King - Bathroom
  • Staypineapple, A Delightful Hotel, South End
Staypineapple, A Delightful Hotel, South End. Image 1 of 28.
1 / 28Staypineapple, A Delightful Hotel, South End
26 Chandler St, Boston, 02116, MA, United States of America
8.4.Very good.
  • Great hotel, fantastic location, beautiful , typical old Boston neighborhood,

    Jul 24, 2021

  • Staff were friendly and accommodating, good location

    Jul 23, 2021

See all 366 reviews

Guests rated location

Dining options
  • Free WiFi
  • Parking available
  • Non-smoking
  • Air Conditioning

Property highlights

Main amenities

  • 56 smoke-free guestrooms
  • Daily housekeeping
  • Free use of bicycles
  • 24-hour front desk
  • Coffee/tea in a common area
  • Laundry service

For families

  • Private bathroom
  • Television
  • Free toiletries
  • Daily housekeeping
  • Hair dryer
  • Coffee/tea maker

What’s around

  • In South End
  • Copley Square - 8 min walk
  • Copley Place - 10 min walk
  • The Freedom Trail - 15 min walk
  • Boston Common - 15 min walk
  • Boston Opera House - 15 min walk

Book this property and collect stamps after your stay

Remember, collect 10 stamps, get 1 reward* night

Enter dates for 2 guests

  • South End Corner King
  • Back Bay King

What’s around


  • In South End
  • Copley Square - 8 min walk
  • Copley Place - 10 min walk
  • The Freedom Trail - 15 min walk
  • Boston Common - 15 min walk
  • Boston Opera House - 15 min walk
  • Prudential Tower - 16 min walk
  • Hynes Convention Center - 18 min walk
  • Northeastern University - 23 min walk
  • Boston Harbor - 25 min walk
  • Massachusetts General Hospital - 26 min walk

Getting around

  • Logan International Airport (BOS) - 7 min drive
  • Boston, MA (BNH-Boston Harbor Seaplane Base) - 15 min drive
  • Portsmouth, NH (PSM-Portsmouth Intl.) - 68 min drive
  • Norwood, MA (OWD-Norwood Memorial) - 32 min drive
  • Bedford, MA (BED-Laurence G. Hanscom Field) - 31 min drive
  • Beverly, MA (BVY-Beverly Municipal) - 33 min drive
  • Lawrence, MA (LWM-Lawrence Municipal) - 36 min drive
  • Boston-Back Bay Station - 7 min walk
  • Boston 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
See on map
26 Chandler St, Boston, 02116, MA, United States of America

At a glance

Hotel size

  • This hotel has 56 rooms
  • This hotel is arranged over 8 floors


  • Check-in time 4 PM-midnight
  • Check-out time is noon

Restrictions related to your trip

  • COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Special check-in instructions

Front desk staff will greet guests on arrival.

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


  • No cribs (infant beds)


  • Pets allowed (dogs only)*
  • Specific rooms only, restrictions apply*
  • 2 per room


  • Free WiFi in public areas
  • Free WiFi in rooms

Other information

  • Smoke-free property
*See small print for additional details or extra charges

In the hotel

Food and drink

  • Coffee/tea in a common area

Things to do

  • Free bicycles on site


  • 24-hour front desk
  • Concierge services
  • Tours/ticket assistance
  • Dry cleaning/laundry service
  • Luggage storage
  • Multilingual staff


  • Number of buildings/towers - 1
  • Year Built - 1900
  • Elevator


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

Languages Spoken

  • Arabic
  • English
  • French
  • Spanish

In the room

Home comforts

  • In-room climate control (air conditioning)
  • Coffee/tea maker
  • Bathrobes
  • Iron/ironing board (on request)

Sleep well

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

Freshen up

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

Be entertained

  • 50-inch flat-screen TV
  • Satellite TV channels
  • IPod docking station

Stay connected

  • Desk
  • Free WiFi
  • Free local calls

Food and drink

  • Free bottled water


  • Daily housekeeping

Small print

Also known as

  • Chandler Inn Hotel 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
  • Chandler Boston

Optional extras

Pets are allowed for an extra charge of USD 25.00 per pet, per night


State tax ID - C0014880350

For details on pet restrictions and to request pet-friendly rooms, contact the property at the number on the booking confirmation.

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).

Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.

This property accepts credit cards. Cash is not accepted.

Mandatory fees

You’ll be asked to pay the following charges at check-in or check-out:
  • Resort fee: USD 17.17 per accommodation, per night

Resort fee inclusions:

  • Sporting facilities or equipment
  • Internet access (may be limited)

We have included all charges provided to us by this property. However, charges can vary, for example, based on length of stay or the unit you book.


  • Yes, Staypineapple, A Delightful Hotel, South End does have fully refundable rooms available to book on our site, which can be cancelled up to a few days before check-in. Just make sure to check this property's cancellation policy for the exact terms and conditions.
  • No, unfortunately, but there's discounted parking nearby.
  • Yes, dogs are welcome, with a limit of 2 per room. There's a charge of USD 25.00 per pet, per night.
  • You can check in from 4 PM - midnight. Check-out time is noon.
  • Yes. Nearby restaurants include Grill 23 & Bar (4-min walk), Barcelona Wine Bar (4-min walk), and The Friendly Toast (4-min walk).
  • No, this hotel doesn't have a casino, but Encore Boston Harbor (6-min drive) is nearby.
  • Have fun during the warmer months with activities such as cycling.
8.4.Very good.
  • 8.0.Very good

    - Fantastic location. - Staff was amazingly helpful, especially Helena. - Only problem was that drains for sink and shower drained slowly

    1 night trip, Jun 23, 2021

    Verified guest review

  • 2.0.Poor

    They should update their website as food wasn’t open as described. We were right next to exit door on floor and we heard lots of loud bangs all night. Bed was nice, but wouldn’t recommend.

    1 night romance trip, Apr 16, 2021

    Verified Expedia guest review

  • 10.0.Exceptional

    It was beautifully decorated and felt bright and happy.

    1 night family trip, Apr 1, 2021

    Verified Expedia guest review

  • 10.0.Exceptional

    I liked that the property was close to public transportation, centrally located in the South End and very close to Back Bay. The staff, especially the manager, Edward, were all great. Check in and out was a breeze, great bed, plenty of storage, and out room was a corner king, so furthest from the elevator and had the most windows.

    3 night trip with friends, Mar 12, 2021

    Verified Expedia guest review

  • 10.0.Exceptional

    Very cute hotel the pineapple decor is just lovely. Staff super friendly.

    R.estrellla, 1 night family trip, Oct 23, 2020

    Verified Expedia guest review

  • 8.0.Very good

    Good Pineapple in Boston

    Not as nice as Pineapples in Chicago, Seattle or Portland, but stll very good. Small rooms. Somewhat isolated area. The manager was exceptionally nice.

    STEVEN, 1 night family trip, Oct 9, 2020

    Verified guest review

  • 2.0.Poor

    Very clean and cute besides no fridge or anything tv in my room didn’t work and also had a very unpleasant experience with one of the workers there. Horrible experience.

    Danielle, 2 night family trip, Aug 25, 2020

    Verified Expedia guest review

  • 10.0.Exceptional

    Dog-friendliest hotel, warm staff, great location

    I stayed here for a few weeks and I honestly haven’t felt more welcome at a hotel. They are also incredibly accommodating to pets (will bring dog bed, bowls, treats, baggies), making it my top choice when traveling with my pet. The location is stellar: Berkeley peek around the corner has great breakfast sandwiches, an amazing restaurant scene is two blocks away on Tremont St, and the shops on Newbury St are a short walk away. I love this business and their staff

    Evanthia E, 2 night trip, Aug 13, 2020

    Verified guest review

  • 10.0.Exceptional

    Safe and convenient location, friendly and considerate staff, cute and clean room- just enough space. Also affordable! Highly recommended.

    Emily, 1 night family trip, Aug 5, 2020

    Verified Expedia guest review

  • 6.0.Good

    Lovely hotel if its 70 degrees or cooler

    This hotel was recently remodeled with a beautiful room design. The rooms have incredibly comfirtable beds! A big plus. For a traveler that isnt going to do any work (theres no desk or table), and is just looking to sleep in their hotel, this is a good spot. Service is fantastic-the team is very attentive. My only gripe is the AC. If you like your room really cold, you wont get that on a really hot day. There is no central AC. That wouldnt have been an issue if it was cooler than 70 degrees. I will definaty stay here again but only between October and April to avoid hotter weather.

    1 night business trip, Jun 18, 2020

    Verified guest review

See all 366 reviews