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From97US$ /night
Check-in
09Jan2026Select date
Check-out
10Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

Amenities

Staypineapple, A Delightful Hotel, offers The Naked Experience, which includes cloud-like European-style individual duvets and cozy robes. Guests enjoy Afternoon Delights from 3:30 PM to 6:30 PM, featuring local coffee and signature pineapple treats. A monthly daily amenity fee provides access to various offerings at a greater value.

Rooms

Guest rooms include plush pillow top beds and upscale amenities like marble tiled bathrooms with walk-in showers. The Back Bay King room accommodates two guests and features the comforts of The Naked Experience. Corner rooms offer additional natural light and partial views of the Boston skyline.

Location

Located in the South End, the hotel is just steps from the Back Bay and significant historical sites. Guests can explore unique boutiques, trendy restaurants, and parks nearby. With Arlington Station a 10-minute walk away, Fenway Park is easily accessible via a short subway ride.

Dining

On-site dining at Trophy Room delivers an all-American menu with classic favorites and original cocktails. Guests can start their day with breakfast in a lively atmosphere. The option for grab-and-go snacks is available throughout the day with locally sourced craft beer and wine.

Pet-Friendly Policies

Staypineapple welcomes pets with its Pineapple Pup Package, which includes dog amenities and treats. Guests can enjoy spacious accommodations while traveling with their pets. Dogs receive a collapsible water bowl and dog waste bag dispenser during their stay.

Highlights

Location: Historic South End, steps from Back Bay

Rooms: The Naked Experience bedding

Dining: Trophy Room with American favorites

Pet-Friendly: Pineapple Pup Package available

Must-do experiences

  • Savor clam chowder at Legal Sea Foods for an iconic treat.
  • Stroll through the Boston Public Market for local flavors and crafts.
  • Visit the Isabella Stewart Gardner Museum for art and beautiful gardens.
  • Catch a Red Sox game at Fenway Park for an unforgettable experience.
  • Explore the vibrant street art in the South End for colorful snapshots.
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
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

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

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, culinary adventures await within the inviting Trophy Room. With a focus on modern American flavors, guests can indulge in a delightful brunch or a cozy dinner in a stylish atmosphere, all just steps from the charm of the South End.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

Modern American
Ambiance
A contemporary yet warm setting, the Trophy Room offers a blend of comfort and sophistication, perfect for relaxing after a day of exploration.
Key Offerings
Brunch delights like avocado toast topped with braised tomatoes and goat cheese, alongside a selection of craft cocktails and wines for dinner.
Reservation
Recommended
Wednesday to Saturday from 4:00 PM to 12:00 AM, and Sunday from 12:00 PM to 8:00 PM.

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
Explore South End
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
Historic park offers lush greenery, walking trails, and the perfect spot for picnics and relaxation in the heart of Boston.
Boston Public Garden
Boston Public Garden
15 minutes' walk
Iconic gardens featuring the famous swan boats and vibrant floral displays, ideal for leisurely strolls and enjoying nature.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
Vibrant shopping and dining hub with historical significance, offering diverse food options and unique shops.
Freedom Trail
Freedom Trail
16 minutes' walk
National Historic Trail running through Boston's iconic sites, showcasing the city's rich Revolutionary history.
Bike Rentals along the Charles River
15 minutes' walk
Biking along the scenic Charles River Esplanade takes you through beautiful parks; rentals available nearby.
Spa Day at Bliss Spa
10 minutes' drive
Indulge in relaxation with massages and treatments at Bliss Spa, providing a serene escape just a short drive away.
Boston Duck Tours
25 minutes' walk
Unique amphibious vehicle tours highlighting Boston's landmarks, providing a fun and thrilling sightseeing experience.
The Trophy Room
The Trophy Room
1 minute' walk
Casual eatery known for American comfort food, featuring a lively atmosphere and classic burgers.
Masa
Masa
3 minutes' walk
Mexican cuisine blends tradition with modern flair in a vibrant setting; famous for their creative cocktails.
Wink & Nod
Wink & Nod
2 minutes' walk
Eclectic cocktail bar with a hidden lounge, offering artisanal drinks and a cozy atmosphere perfect for couples.
House of Blues
20 minutes' walk
Live music venue hosting a range of genres; known for its vibrant atmosphere and Southern-inspired menu.
The Wilbur Theater
20 minutes' walk
Historic theater featuring comedy shows and concerts, known for its charming interior and engaging events.
Laugh Boston
10 minutes' drive
Comedy club specializing in stand-up; offers a fun night out with local and renowned comedians performing regularly.
Getting around
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
FAQs
About Staypineapple, A Delightful Hotel, South End
What is the check-in and check-out policy at Staypineapple, A Delightful Hotel, South End?
Check-in is from 16:00 and check-out is by 12:00.
What are the distances to nearby attractions from Staypineapple, A Delightful Hotel, South End?
Popular attractions include Fenway Park (1 km), the Museum of Fine Arts (2 km), and the Freedom Trail (1 km).
Is there on-site dining available at Staypineapple, A Delightful Hotel, South End?
The hotel's on-site restaurant, Trophy Room, serves an all-American menu for brunch, dinner, and late drinks.
Does Staypineapple, A Delightful Hotel, South End offer free Wi-Fi?
Guests can enjoy complimentary high-speed Wi-Fi throughout the hotel.
What amenities are available in the rooms at Staypineapple, A Delightful Hotel, South End?
Rooms feature air conditioning, a flat-screen TV, coffee maker, and designer bath products.
Which restaurants are located near Staypineapple, A Delightful Hotel, South End?
Nearby dining options include Berkeley Perk Café (0.5 km), Masa (0.5 km), and Grill 23 & Bar (0.5 km).
Are there any recreational activities offered at Staypineapple, A Delightful Hotel, South End?
Bicycles are available for rent, allowing guests to explore the city with ease.
Does Staypineapple, A Delightful Hotel, South End have any notable features?
The hotel features the unique Naked Experience, which includes European-style individual duvets and cozy robes.
What are the hotel highlights of Staypineapple, A Delightful Hotel, South End?
Highlights include a bar/lounge area, 24-hour reception, luggage storage, and vintage fittings throughout.

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