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From97US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

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

Rooms: Naked Experience

Staypineapple Boston features rooms with plush pillow top beds, European-style double duvets, and high-speed Wi-Fi. Each room includes a flat-screen TV, an iPod docking station, a work desk, and a telephone with 24-hour front desk access. Rooms also provide your choice of coffee or tea for the in-room Keurig. The Naked Experience includes two fluffy duvets, soft white linens, and a cushiony mattress topper. The South End Corner King offers added quiet.

Dining: Trophy Room & Café

The Trophy Room is a long room lined with windows overlooking the street. It features a menu of familiar favorites and original cocktails, including the Trophy Wife, made with passion fruit and elderflower laced vodka. The adjacent Berkeley Perk Café serves cooked items, such as breakfast tacos and omelettes. Guests can enjoy signature pineapple treats. Quick Bites & Bevvies offers snacks, beer, wine, and other refreshments.

Leisure & Hotel Amenities

Guests can use help-yourself coffee in the lobby. High-speed wireless Internet access is available on unlimited devices. Water Bar is available for refills. Each afternoon, the hotel offers pineapple treats and coffee in the lobby. The Trophy Room often features a football game or trivia. Beach cruisers are available for guests to explore the city.

Location & Transportation

Staypineapple Boston is on the border of Back Bay and South End. It is near the Freedom Trail, Boston Public Library, and Boston Public Garden. Fenway Park is 2 km away. The hotel is within a 10-minute walk to Arlington Station for Green Line D access to Fenway Park. The summer-to-December SoWa Open Market and SoWa First Fridays are nearby. It's in Downtown Boston, home to Freedom Trail sites like the Old State House and Faneuil Hall Marketplace.

Services & Conveniences

The hotel includes a 24-hour front desk. Bikes are available. A reusable PATH water bottle is provided. The Daily Amenity Fee covers access to amenities. The CORE Welcome Drink includes a choice of house wine, beer, or non-alcoholic beverages. The hotel is dog-friendly, with the Pineapple Pup Package available.

“In my opinion, Staypineapple distinguishes itself with its playful pineapple theme and dog-friendly atmosphere. I found the location, bordering Back Bay and South End, especially appealing. Its quirky charm is enhanced by the Naked Experience bedding and complimentary bikes, making it a memorable stay.”
Hotel logo
Harper CollinsEditor, UsBoston
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Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
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

Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

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 in South End, culinary experiences await just steps from the historic heart of the city. The onsite dining options feature modern American cuisine in a vibrant setting, perfect for travelers seeking both comfort and flavor.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

Modern American
Ambiance
A chic and contemporary space with an inviting atmosphere, ideal for socializing and relaxing.
Key Offerings
Highlights include delightful brunch options and savory dinner selections, with signature dishes like avocado toast topped with braised tomatoes and goat cheese.
Reservation
Recommended for dinner to ensure a table.
Wednesday to Saturday from 4:00 PM to Midnight, and Sunday from 12:00 PM to 8:00 PM.

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
Explore Boston
Explore Boston's Best
Top Attractions
Activities
Dining
Entertainment
Boston Common
15 minutes' walk
America's oldest public park features lush landscapes and historical significance, perfect for a leisurely stroll or picnic.
Faneuil Hall Marketplace
25 minutes' walk
A bustling hub for shopping and dining, known for its vibrant atmosphere and street performers. A must-visit landmark.
Museum of Fine Arts
25 minutes' walk
Renowned for its vast collection, this museum offers a unique look at art from around the world, with special exhibits often.
Freedom Trail
16 minutes' walk
A 2.5-mile path that connects 16 historical sites, ideal for history enthusiasts and self-guided tours.
Cycle along the Charles River
15 minutes' drive
Bike rentals available near the river, offering scenic views and peaceful pathways for active exploration.
Relax at Boston Public Garden
15 minutes' walk
Stunning flowerbeds and swan boats provide a tranquil escape. Great for picnics or leisurely walks.
The Trophy Room
1 minute walking
Casual eatery with American fare and a friendly atmosphere. Known for burgers and craft beers.
Masa
3 minutes' walk
A trendy Mexican restaurant offering delicious tacos and margaritas in a lively setting. Reservations recommended.
Laugh Boston
15 minutes' drive
A comedy club featuring local talents and headliners, making it a fun night out for all ages.
Royal Boston Theatre
12 minutes' walk
Showcasing various performances from theater to music events. A great spot for family-friendly entertainment.
Local transportation
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
FAQs
About Staypineapple, A Delightful Hotel, South End

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