Staypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photo
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From97US$ /night
Check-in
14Jun2026Select date
Check-out
15Jun2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116
Great
8.5
9.0
/10
4.1
4.2
/5

Boutique hotel in Boston's South End featuring the exclusive Naked Experience bedding

Amenities

Staypineapple, A Delightful Hotel, South End offers a Daily Amenity Fee that covers coffee, signature pineapple treats during Daily Afternoon Delights, and unlimited still, sparkling, or hot water from the Water Bar. Guests receive a refillable metal water bottle upon arrival and can use complimentary bicycles to explore the city. The hotel also provides high-speed Wi-Fi and streaming-capable flat-screen TVs in every room.

Rooms

Each guest room includes the exclusive Naked Experience bedding with European-style individual duvets and a walk-in marble shower. Rooms are equipped with a flat-screen TV, iPod docking station, and a work desk with telephone. The hotel features genuine vintage fittings and clean, stylish decor with upscale amenities.

Dining

On-site dining is available at the Trophy Room, which serves an all-American menu in a lively bar setting. Guests can enjoy complimentary coffee and signature pineapple treats during the Daily Afternoon Delights in the lobby. The bar also offers a welcome drink for guests upon check-in.

Location

The hotel is centrally located on the border of Back Bay and the South End, within walking distance of Fenway Park, Back Bay station, and Boston Center for the Arts. Scenic Back Bay and Newbury Street's shops and restaurants are less than a 10-minute walk away. The Boston Common and Amtrak station are also easily reachable on foot.

Pet-Friendly

Staypineapple is a pet-friendly hotel with specialized dog amenities including pet baskets and pet bowls in the lobby. The hotel partners with a local dog rescue organization and welcomes dogs with treats and water bowls. Guests can also enjoy the friendly presence of the general manager's Bernedoodle, Goofy, during their stay.

Highlights

Location: Border of Back Bay and South End, 10 min walk to Newbury Street

Rooms: Naked Experience bedding with European-style individual duvets

Dining: Trophy Room with all-American menu and welcome drink

Amenities: Daily Amenity Fee covers coffee, treats, and water bar

Pet-Friendly: Dog amenities, pet baskets, bowls, and rescue partnership

Transport: Complimentary bicycles for city exploration

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Select your room type

Staypineapple, A Delightful Hotel, South End offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
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

Price and Room Availability Calendar

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Facilities

Experience a variety of amenities at the boutique hotel, crafted to ensure your comfort and unforgettable moments
Facilities: Great
8.4/10Review score

General

  • No smoking on site
  • 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

Staypineapple, A Delightful Hotel, South End 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
Getting around
City Centre
Boston20 min  ·  1.0 mi
Airports
Logan (BOS)13 min  ·  5.3 mi
Worcester Regional (ORH)116 min  ·  47.7 mi
Train
Boston South Station17 min  ·  4600 ft
Underground
Back Bay Metro Station5 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
Wireless 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

Reviews and Ratings

Feedback about Staypineapple, A Delightful Hotel, South End from previous guests about their experience.
Review score
Based on 917 verified reviews
8.7/10
Great
85%
Recommend
Breakfast
7.5/10
Cleanliness
8.9/10
Comfort
8.8/10
Facilities
8.4/10
Free Wi-Fi
7.6/10
Location
9.2/10
Paid Wi-Fi
7.6/10
Staff
9.2/10
Value for money
8.1/10
Guest reviews
based on 61 reviews
3.5/5
based on 879 reviews
8.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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Check-in
14Jun2026Select date
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15Jun2026Select date
Rooms and Guests2 Guests, 1 Room