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Staypineapple, A Delightful Hotel, South End
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73 photos

Staypineapple, A Delightful Hotel, South End, Boston

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Check rooms and rates
From97US$ /night
Check-in
01Feb2026Select date
Check-out
02Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116
Great
8.4
9.0
/10
4.1
4.2
/5
“The hotel is perfectly situated just a short stroll from the train station, making it super convenient to explore the charming neighborhood.”view full review

Staypineapple, A Delightful Hotel, South End offers a modern hotel experience, featuring unique touches like The Naked Experience and a vibrant on-site restaurant. This award-winning Boston hotel is located at the intersection of Back Bay and South End, providing convenient access to local attractions.

Rooms & Amenities

Staypineapple features thoughtfully designed rooms with plush pillow-top beds, European-style double duvets, and upscale amenities like high-speed Wi-Fi and designer bath products. The South End Corner King provides added quiet and natural light, while the Back Bay King room is perfect for travelers seeking comfort with its walk-in shower.

Dining & Refreshments

On-site dining is offered at the Trophy Room, which serves an American menu with options for brunch, dinner, and drinks. Guests can enjoy signature pineapple treats and local coffee during Afternoon Delights in the lobby.

Leisure & Local Area

Staypineapple provides complimentary bikes for exploring the city and is situated within walking distance to the Boston Public Garden, Fenway Park, and entertaining events at the Boston Center for the Arts. The location also offers convenient access to public transportation including Arlington Station for direct trains to Fenway Park.

Services & Accessibility

Additional services include a 24-hour front desk, high-speed internet access, and help-yourself coffee in the lobby. The hotel also features the DOG FRIENDLY Pineapple Pup Package, making it suitable for pet owners.

View all

Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
South End Corner King
South End Corner King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Back Bay King
Back Bay King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
room details

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences
Charming Design!
“The room decor was innovative and thoughtfully curated, making our stay a good visual experience.” view full review
Cozy Comfort
“The bed was exceptionally cozy, and the room included unique space-saving features that enhanced our comfort.” view full review
Spotless & Cute
“The bathroom was not only immaculate but also had charming details that made it a pleasure to use.” view full review
Convenient Amenities
“The provision of tea, coffee, and complimentary bottled water in the room made our stay even more enjoyable and convenient.” view full review

General

  • No smoking on site
  • Free Wi-Fi
  • 24-hour reception
  • Pets allowed
  • Luggage storage
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access

Services

  • Pet amenities available
  • Housekeeping

Dining

  • Restaurant
  • Bar/ Lounge area

Room features

  • Air conditioning
  • Heating
  • Tea and coffee facilities
  • Ironing facilities

Media

  • Flat-screen TV
Show more

Location

26 Chandler St, Boston, Massachusetts, United States, 02116
Map view
26 Chandler St, Boston, Massachusetts, United States, 02116
City landmarks
Stadium
Fenway Park
1.4 mi
Landmark
Boston Common
3900 ft
Market
Faneuil Hall Marketplace
1.4 mi
Park
Boston Public Garden
4100 ft
Landmark
Freedom Trail
4200 ft
Museum
Museum of Fine Arts
1.3 mi
Aquarium
New England Aquarium
1.4 mi
Museum
Museum of Science
1.4 mi
Museum
Boston Tea Party Ships & Museum
1.3 mi
Library
Boston Public Library
2900 ft
Parking area
Skywalk Observatory
3700 ft
Square
Copley Square
2600 ft
Landmark
North End
1.5 mi
Spa Centre
Newbury Street
3900 ft
Landmark
Freedom Trail walk
1.6 mi
Church
Trinity Church
2200 ft
Cemetery
Granary Burying Ground
5100 ft
Landmark
Boston Children's Museum
1.5 mi
Tower
John Hancock Tower
2100 ft
Monument
New England Holocaust Memorial
1.3 mi
Monument
Bunker Hill Monument
2.1 mi
Museum
The Paul Revere House
1.4 mi
Landmark
Beacon Hill
1.2 mi
Museum
Isabella Stewart Gardner Museum
1.6 mi
Landmark
Quincy Market
1.3 mi
Museum
The Institute of Contemporary Art
1.5 mi
Public Building
Old State House
1.2 mi
Museum
USS Constitution Museum
2.0 mi
Theatre
Boston Symphony Hall
5100 ft
Landmark
Back Bay
3100 ft
Nearby
Boston Public Garden Facing the Arlington Street Entrance
George Washington Statue
1400 ft
Arlington Street Boston Public Garden
Ether Monument
1400 ft
Church
Arlington Street Church
1400 ft
Restaurants
The Trophy Room
0 ft
26 Chandler Street
Wink & Nod
500 ft
3 Appleton St
Masa
600 ft
439 Tremont Street
Cosmica
600 ft
40 Berkeley St Located in the Revolution Hotel
Bootleg Special
700 ft
400 Tremont St
Club Cafe
1000 ft
209 Columbus Ave
Flour Bakery & Cafe
1300 ft
131 Clarendon St
Barcelona Wine Bar
1100 ft
525 Tremont Street
Citrus & Salt
900 ft
142 Berkeley St
The Beehive
1300 ft
541 Tremont St
Getting around
City Centre
Boston20 min  ·  1.0 mi
Airports
Logan International Airport (BOS)13 min  ·  5.3 mi
Worcester Regional Airport (ORH)116 min  ·  47.7 mi
Train
Boston South Station17 min  ·  4600 ft
Underground
Back Bay5 min  ·  1400 ft
Bus
Bus stop2 min  ·  400 ft
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Property information and rules
Check-in
from 16:00-23:59
Check-out
until 12 pm
Guest Parking
No parking available.
Internet
is available in for free.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are allowed on request.
Year renovated:
2011
Number of floors:
8
Number of rooms:
56
Former name
Chandler Inn Hotel

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Check-in
01Feb2026Select date
Check-out
02Feb2026Select date
Rooms and Guests2 Guests, 1 Room
  • Overview
  • Rooms
  • Price calendar
  • Facilities
  • Location
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