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From97US$ /night
Check-in
09Feb2026Select date
Check-out
10Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview and Details

26 Chandler St, Boston, Massachusetts, United States, 02116
-
Close to the Boston Public Garden
Great
8.4
9.0
/10
4.1
4.2
/5

Amenities

Staypineapple Boston provides The Naked Experience, featuring cloud-like individual duvets and daily Afternoon Delights with coffee and signature pineapple treats. The daily amenity fee simplifies access to various services and activities that enhance the guest experience. Guests can utilize high-speed wireless Internet on unlimited devices, stream on high-definition TVs, and refill water bottles at the Water Bar in the lobby.

Rooms

The hotel's rooms include the Back Bay King, furnished with a king-sized bed and a spacious walk-in shower. The South End Corner King offers extra natural light and partial city views. Each room features a PATH water bottle pre-filled with purified drinking water and unlimited refills at the lobby Water Bar.

Location

Staypineapple Boston is located in the South End, steps away from Back Bay and many historic sites. The hotel is within walking distance to unique boutiques, trendy restaurants, and the Boston Center for the Arts. Arlington Station, just a 10-minute walk away, provides easy access to Fenway Park and other attractions via the Green Line.

Dining

Trophy Room, the on-site restaurant, offers a menu of American classics with options for breakfast and dinner. Guests can enjoy lively weekend breakfasts with performances at Trophy Room. Quick Bites & Bevvies provides snacks, drinks, and locally sourced craft beer available for purchase in the lobby.

Pet-Friendly

The hotel welcomes pets through the Pineapple Pup Package, which includes treats and a collapsible water bowl. Dogs can enjoy accommodations while their owners explore the city. This package supports local businesses focused on creating jobs for military veterans and women.

Highlights

Location: South End, steps from Back Bay

Dining: Trophy Room offers American classics

Rooms: The Naked Experience with luxury linens

Pet-Friendly: Pineapple Pup Package available

Must-do experiences

  • Stroll along the historic Freedom Trail for a slice of American history.
  • Indulge in a lobster roll at James Hook & Co. for local flavors.
  • Visit the Isabella Stewart Gardner Museum for stunning art and gardens.
  • Explore the bustling Boston Public Market for local crafts and food.
  • Catch a game at Fenway Park for an unforgettable sports experience.
View all

Choose Your Room Category

The hotel offers a range of accommodations including doubles, family rooms, and suites—plus breakfast, free cancellation, and special rates.
South End Corner King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
Back Bay King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine

Room Availability and Pricing Calendar

Find available rooms and check today's best prices!

Facilities

This hotel provides premium amenities for a memorable and relaxed stay

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

Dining Onsite

At Staypineapple, A Delightful Hotel, South End, guests can indulge in the vibrant flavors of American cuisine at the Trophy Room, where modern decor meets a casual atmosphere. Enjoy a delightful brunch or dinner while surrounded by the charm of the lovely South End neighborhood.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American
Ambiance
Modern with a welcoming vibe
Key Offerings
Signature dishes include rich avocado toast with braised tomatoes and goat cheese, paired with a selection of craft cocktails. Enjoy the charm of South End's trendy neighborhood while dining.
Reservation
Recommended
Wednesday to Saturday: 4:00 PM - 12:00 AM; Sunday: 12:00 PM - 8:00 PM.

Hotel Location

26 Chandler St, Boston, Massachusetts, United States, 02116
Map view
26 Chandler St, Boston, Massachusetts, United States, 02116
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
Explore Boston
Explore Boston's Best
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
The oldest public park in the U.S., featuring lush landscapes and walking paths, perfect for a relaxing stroll.
Freedom Trail
Freedom Trail
16 minutes' walk
A historic 2.5-mile route showcasing Boston's significant sites, ideal for history enthusiasts and guided tours.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Home to an extensive collection of artworks, this museum offers guided tours and free admission on designated days.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
A vibrant marketplace featuring shops and eateries, where you can enjoy street performances and seasonal events.
Yoga at Boston Common
15 minutes' walk
Outdoor yoga sessions held in the park, offering relaxation amidst nature for all skill levels; check for seasonal offerings.
Biking the Esplanade
10 minutes' drive
Rent a bike and explore the scenic Charles River Esplanade, perfect for thrill-seeking cyclists; rental services available nearby.
The Trophy Room
The Trophy Room
1 minute' walk
A casual eatery with an American menu; try the signature burgers and local brews. Reservations recommended during peak times.
Masa
Masa
3 minutes' walk
A vibrant atmosphere featuring Southwestern cuisine; known for its margaritas and fresh ingredients. Dietary options available.
Laugh Boston
10 minutes' drive
Comedy club featuring national headliners and local talent; family-friendly shows available. Reservations are advised for popular nights.
House of Blues
15 minutes' walk
Live music venue with a lively atmosphere; hosts a variety of musical acts and themed nights. Perfect for all ages.
Navigating city
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
Questions of the users
About Staypineapple, A Delightful Hotel, South End
Are there any parking options available in the vicinity of the hotel, and if so, what is the cost?
10 November 2024
A recommended parking option nearby is the Clarendon Garage at 100 Clarendon Street, which charges $36 per night.
Does the hotel provide a luggage storage service for guests before check-in or after check-out?
12 December 2024
Guests can store their luggage in a secure area prior to checking in or after checking out.
Is there an elevator in the hotel for easy access to different floors?
5 January 2025
Yes, the hotel is equipped with an elevator for guest convenience.
What does the term 'Naked Experience' refer to, and what can guests expect from it?
15 February 2025
The Naked Experience offers a cozy, luxurious night's sleep with freshly laundered bedding and cloud-like European-style duvets.
Can guests rely on Wi-Fi access during their stay, and is there any laundry service available nearby?
20 March 2025
High-speed Wi-Fi is available throughout the hotel, including in all rooms. Laundry services are accessible from nearby providers.
Is the hotel welcoming to guests traveling with pets, and what are the associated fees?
25 April 2025
The hotel is dog-friendly and charges a pet fee of $25 per night, which includes amenities such as a dog bed and treats.
What is the breakfast arrangement for guests during their stay?
30 May 2025
Currently, the hotel does not provide a continental breakfast, but several local restaurants nearby offer breakfast options.
What is the best way to reach the airport from Staypineapple?
5 June 2025
Ride-share services such as Uber or Lyft are recommended for convenient transportation to the airport.
Are the bathrooms in the guest rooms private, or are they shared?
10 July 2024
All rooms feature private bathrooms for the comfort and privacy of guests.
What amenities are provided in the bathrooms, specifically concerning hair dryers?
15 August 2025
Every room is equipped with a blow dryer for guest convenience.
Is there a facility to prepare hot beverages like tea in the rooms?
20 September 2025
Keurig machines in the rooms can produce hot water, allowing guests to enjoy tea or coffee at their convenience.
Can a name be added to an existing reservation if needed?
25 October 2025
Yes, it is possible to add a name to an existing reservation.

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