Book with us
—up to 10% cheaper
than on Booking.com
Check rooms and rates
From97US$ /night
Check-in
13Jan2026Select date
Check-out
14Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

Offering a location within 500 metres of Blue Man Group, Staypineapple, A Delightful Hotel, South End Boston offers 56 rooms. One will enjoy a coffee bar or a shared lounge and various recreational opportunities, while this hotel also boasts prime setting within a few blocks of the Trinity Church.

Location

The baseball stadium "Fenway Park" is 2.3 km from the comfortable hotel, and Museum of Science is located a 10-minute drive away. You'll be 450 metres from The Lagoon.

Boston Common Public Park is a 15-minute walk away, and Back Bay is a few steps from the Staypineapple.

Guests will find themselves 2.8 km from Beacon Street train station and just 250 m from Arlington city rail.

Rooms

The rooms include ironing equipment, along with such modern comforts as a flat-screen TV with satellite channels.

Eat & Drink

Serving American dishes, Grill 23 & Bar lies a stone's throw from the 4-star Staypineapple, A Delightful Hotel, South End.

Leisure & Business

Guests may also participate in bicycle usage.

“Staypineapple charms with its playful pineapple theme and thoughtful perks like complimentary bikes; its location on the Back Bay-South End border puts much of Boston within easy reach. I especially appreciate the pet-friendly vibe and the unique 'Naked Experience' bedding, promising a cozy night's sleep. It's a fun, well-situated base for exploring the city.”
Hotel logo
James DavidEditor-in-Chief at Dogfriendly-hotels
View all

Select your room type

The hotel provides many room choices—family rooms, doubles, and pet-friendly suites—with breakfast, free cancellation, and special offers
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

Rates & availability calendar

See current prices and availability for your chosen dates!

Facilities

Hotels feature amenities designed to keep both you and your pet comfortable

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, dining is a charming exploration of modern American flavors. Guests can indulge in a vibrant atmosphere with locally-inspired dishes and the warmth of the South End neighborhood, making every meal a memorable experience.
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 cheerful atmosphere with a contemporary design, perfect for both casual gatherings and intimate dinners.
Key Offerings
Discover a delightful array of offerings, including a standout avocado toast topped with braised tomatoes and goat cheese, ideal for brunch or dinner alongside a selection of craft cocktails.
Reservation
Reservations are 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
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
The oldest city park in the U.S., featuring expansive green spaces, walking paths, and historical monuments.
Boston Public Garden
Boston Public Garden
15 minutes' walk
Famous for its swan boats and vibrant flowerbeds, this tranquil garden offers picturesque views and relaxation spots.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Home to a vast collection of artistic masterpieces, with free admission days available for visitors. Worth a visit.
Freedom Trail
Freedom Trail
16 minutes' walk
A 2.5-mile-long path through historic Boston, featuring 16 significant sites that tell America's Revolutionary history.
Biking along the Charles River
10 minutes' drive
Scenic biking paths perfect for all levels. Rentals available nearby. Ideal for active travelers.
Yoga at Boston Common
15 minutes' walk
Outdoor yoga sessions provide relaxation amidst nature. Check seasonal schedules for classes.
Visit Newbury Street
15 minutes' walk
Shopping and culture merged on this famous street, featuring boutique stores and coffee shops.
The Trophy Room
The Trophy Room
1 minute' walk
Casual eatery with an eclectic menu. Famous for its burgers and craft cocktails. Reservations recommended.
Masa
Masa
3 minutes' walk
New Mexican cuisine in a vibrant setting. Signature dishes include enchiladas and tacos. Great for families.
Wink & Nod
Wink & Nod
2 minutes' walk
Innovative cocktails and unique dishes in a cozy vibe. Ideal for couples' nights out. Reservations suggested.
The Wilbur Theatre
10 minutes' drive
A historic venue hosting live performances, including comedy shows and concerts. Check the schedule for events.
House of Blues
15 minutes' drive
Famous music venue featuring a vibrant nightlife atmosphere with live bands. Great for music lovers.
Laugh Boston
10 minutes' drive
Comedy club offering stand-up performances. Perfect for a fun night out with friends, suitable for all ages.
Local transport and travel 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
Want access to early-bird pet-friendly hotel deals?
Access exclusive discounts today!
Check Rates
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 time is check-in and check-out at Staypineapple, A Delightful Hotel, South End?
Check-in is from 16:00 and check-out is by 12:00.
How far is Staypineapple, A Delightful Hotel, South End from Boston Logan International Airport?
The hotel is approximately 7 km from Boston Logan International Airport, which takes about 15 minutes by car.
What dining options are available at Staypineapple, A Delightful Hotel, South End?
The on-site Trophy Room offers a lively dining scene with an all-American menu.
Are there any notable attractions near Staypineapple, A Delightful Hotel, South End?
Nearby attractions include Fenway Park (1 km), Museum of Fine Arts (2 km), and the Freedom Trail (1 km).
Does Staypineapple, A Delightful Hotel, South End offer parking facilities?
The hotel provides limited on-site parking for a fee.
What amenities can guests expect in the rooms at Staypineapple, A Delightful Hotel, South End?
Rooms feature a flat-screen TV, free Wi-Fi, air conditioning, a work desk, and upscale designer bath products.
Is breakfast available at Staypineapple, A Delightful Hotel, South End?
While the hotel does not serve breakfast, the nearby Berkeley Perk Café is 0.5 km away and offers breakfast options.
Does Staypineapple, A Delightful Hotel, South End provide any business services?
The hotel has a 24-hour front desk and offers free Wi-Fi throughout the property.
Are there recreational activities available at Staypineapple, A Delightful Hotel, South End?
Guests can use the complimentary bicycles provided by the hotel to explore the city.

Next best alternative

Consider them for your next trip.
Check-in
13Jan2026Select date
Check-out
14Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near Staypineapple, A Delightful Hotel, South End
The Revolution Hotel Boston Interior photo
Mobile-only price

The Revolution Hotel Boston

8.4
Great4281 reviews
119m from property
USD 103USD 92
per night
Hotel Aka Back Bay Boston Room photo
Mobile-only price

Hotel Aka Back Bay Boston

8.8
Great813 reviews
282m from property
USD 204USD 183
per night
Raffles Boston Hotel Exterior photo
Mobile-only price

Raffles Boston Hotel

9.2
Perfect118 reviews
359m from property
USD 580USD 522
per night