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From97US$ /night
Check-in
07Jan2026Select date
Check-out
08Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview

26 Chandler St, Boston, Massachusetts, United States, 02116
-
Close to Copley Square
Great
8.4
9.0
/10
4.1
4.3
/5

Staypineapple, A Delightful Hotel, South End - Modern hotel with The Naked Experience near Back Bay

Located on the border of Back Bay and South End, Staypineapple Boston offers a central location within walking distance of historical sites, restaurants, and Fenway Park. The hotel features The Naked Experience, which includes European-style duvets, cozy robes, and oversized towels. Guests have access to high-speed Wi-Fi, designer bath products, and in-room Keurig coffee makers. The Trophy Room bar serves cocktails like the Trophy Wife (vodka with passion fruit and elderflower) and is open until 2am daily. The adjacent Berkeley Perk Café provides breakfast options like omelets and tacos. The hotel is steps from the SoWa Open Market and SoWa First Fridays art market.

Additional perks of the hotel

Free lobby coffee and pineapple treats in the afternoon

Complimentary use of yellow beach cruiser bikes

Reusable PATH water bottles with refill stations in the lobby

Dog-friendly accommodations with Pineapple Pup Package available

24-hour front desk service and streaming-capable HDTVs in rooms

Rooms

All rooms include plush pillow-top beds with European-style double duvets, high-speed Wi-Fi, and designer bath products. The Back Bay King features a king-size bed and walk-in shower. The South End Corner King offers additional natural light and partial city views. Rooms are equipped with 50-inch HDTVs with streaming capability, iPod docking stations, and work desks. Charging points are integrated into bedside tables with crystal lamps.

Other conveniences

Marble-tiled bathrooms with walk-in showers

Signature lightweight robes

Unlimited in-room Keurig coffee and tea service

Ironing facilities and air conditioning

Flat-screen TVs with streaming services

Must-do experiences

  • Visit the Boston Tea Party Ships for a fun, historical reenactment.
  • Try a classic lobster roll at Neptune Oyster in the North End.
  • Stroll through the hidden Arnold Arboretum for serene nature trails.
  • Explore the exhibits at the Isabella Stewart Gardner Museum.
  • Don't miss the vibrant Boston Public Market for local artisan foods.
View all

Choose Your Room

Our listed hotels offer a variety of room types—double rooms, family suites, or deluxe options—all with features like breakfast, flexible cancellation policies, and exclusive deals.
South End Corner King
2 persons
18 m² 
1 King-size bed
Shower
Coffee machine
Back Bay King
2 persons
18 m² 
1 King-size bed
Shower
Coffee machine

Room Rates & Availability Tracker

Find Deals for Your Travel Dates

Amenities

Thoughtful hotel amenities for a comfortable 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

Staypineapple, A Delightful Hotel, South End offers a distinctive dining experience that captures the essence of modern American cuisine. Guests can savor dishes prepared with care in a stylish, inviting ambiance that reflects the vibrant spirit of the charming 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 and inviting, the Trophy Room features a sleek design that fosters a relaxed yet chic dining atmosphere.
Key Offerings
Delight in weekend brunch featuring tempting options like avocado toast topped with braised tomatoes and goat cheese. The dinner menu emphasizes comfort food reimagined, ensuring every bite is a pleasure.
Reservation
Recommended
Brunch on Sunday from 12:00 PM to 8:00 PM; Dinner Wednesday to Saturday from 4:00 PM to midnight.

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
400 m
Arlington Street Boston Public Garden
Ether Monument
400 m
Church
Arlington Street Church
400 m
Restaurants
The Trophy Room
0 m
26 Chandler Street
Wink & Nod
150 m
3 Appleton St
Masa
170 m
439 Tremont Street
Cosmica
160 m
40 Berkeley St Located in the Revolution Hotel
Bootleg Special
200 m
400 Tremont St
Club Cafe
280 m
209 Columbus Ave
Flour Bakery & Cafe
390 m
131 Clarendon St
Barcelona Wine Bar
320 m
525 Tremont Street
Citrus & Salt
270 m
142 Berkeley St
The Beehive
390 m
541 Tremont St
Explore Boston
Local Highlights
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
A historic park featuring scenic paths and the iconic Frog Pond; perfect for family picnics and seasonal events.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Housing an extensive art collection from around the world; offers special exhibitions and free admission days.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
A vibrant market with shops and eateries, famous for street performances and local foods; vibrant atmosphere every day.
Freedom Trail
Freedom Trail
16 minutes' walk
A 2.5-mile historic walking trail featuring significant sites from the American Revolution; guided tours available.
Biking the Charles River
15 minutes' walk
Enjoy scenic views overlooking the river with bike rentals available nearby; a rejuvenating experience for all.
Boston Tea Party Ships & Museum
Boston Tea Party Ships & Museum
25 minutes' walk
An interactive experience where visitors can relive the famous event; includes guided tours and historical reenactments.
The Trophy Room
The Trophy Room
1 minute' walk
An upscale pub atmosphere offering comfort food and craft cocktails; ideal for casual meals or special occasions.
Wink & Nod
Wink & Nod
2 minutes' walk
A speakeasy-style bar with innovative cocktails and small plates; a cozy spot for date nights or laid-back gatherings.
House of Blues
15 minutes' walk
A renowned live music venue featuring performances across genres; check the schedule for all-ages shows.
The Wilbur Theatre
25 minutes' walk
Historic theater hosting comedy, live music, and performances; offers a captivating experience in an elegant setting.
Transportation Tips
City Centre
Boston20 min  ·  1.6 km
Airports
Logan International Airport (BOS)13 min  ·  8.6 km
Worcester Regional Airport (ORH)116 min  ·  76.7 km
Train
Boston South Station17 min  ·  1.4 km
Underground
Back Bay5 min  ·  400 m
Bus
Bus stop2 min  ·  100 m
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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
Is there a parking option nearby, and what are the costs associated?
01 November 2024
There is a parking garage located at 100 Clarendon Street, with an overnight rate of $36 plus taxes.
Can luggage be stored before check-in or after check-out?
05 January 2025
A secure area is available for guests to store their luggage before check-in and after check-out.
Are elevators available in the hotel for easy access?
12 February 2025
Yes, there are elevators throughout the hotel for guest convenience.
What is the 'Naked Experience' at Staypineapple all about?
20 March 2025
The Naked Experience promises a cozy, luxurious night with freshly laundered bedding and cloud-like European-style duvets for a restful sleep.
Is Wi-Fi available in the hotel for work-related needs?
23 April 2025
Wi-Fi is available throughout the hotel and in all guest rooms for your connectivity needs.
Is the hotel accommodating to pets?
30 May 2025
The hotel is pet-friendly with a nightly fee of $25, which includes a dog bed, treats, waste bags, and bowls.
Are there breakfast options available near the hotel?
15 June 2025
While the on-site restaurant is currently closed for breakfast, there are several nearby restaurants that serve breakfast.
How can guests reach the airport from the hotel?
22 July 2025
Ride-share services like Uber or Lyft are convenient options for getting to the airport.
Do all rooms have private bathrooms for guest convenience?
09 August 2024
Yes, each room is equipped with a private bathroom ensuring comfort and privacy.
Are coffee and tea making facilities available in the rooms?
03 September 2025
In-room Keurig machines are provided, which can also dispense hot water for tea, along with various coffee options.
Is there a way to include additional names on an existing reservation?
14 October 2024
Adding a name to an existing reservation is possible and easily arranged.

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