Welcome to Staypineapple, A Delightful Hotel, South End – Boston

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From97US$ /night
Check-in
10Dec2025Select date
Check-out
11Dec2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

Amenities

Staypineapple, A Delightful Hotel offers the distinctive Naked Experience, featuring cloud-like European-style individual duvets and cozy robes. Afternoon Delights provide guests with signature pineapple treats and local coffee from 3:30 PM to 6:30 PM. The hotel also promotes sustainability with reusable PATH water bottles and a Water Bar for unlimited refills on purified water.

Rooms

The hotel accommodates various guests with room types like the Back Bay King, which includes a plush king bed and high-definition streaming-enabled TV. Each room offers complimentary high-speed Wi-Fi and a marble-tiled bathroom featuring a walk-in shower. Corner rooms provide additional natural light and partial views of the city skyline.

Location

Situated in Boston's South End neighborhood, the hotel is steps away from Back Bay and numerous historical sites. Guests can explore the nearby Boston Center for the Arts and enjoy local boutiques and cafes within walking distance. Quick access to Arlington Station allows easy transportation to Fenway Park and other iconic attractions.

Dining

Trophy Room, the hotel's on-site bar and restaurant, serves a menu that combines classic American favorites and original cocktails. Breakfast offerings and lively weekend performances create an inviting atmosphere for both locals and travelers. Evening dinner options also cater to a wide range of palates, making it a hub for dining in the South End.

Pet-Friendly Policies

Staypineapple welcomes pets with its Pineapple Pup Package, offering dog treats and essential amenities. Guests receive a collapsible water bowl and waste bag dispenser as part of the package. Dogs are allowed in designated areas, ensuring an accommodating stay for pet owners.

Highlights

Location: Steps away from Back Bay

Dining: Trophy Room with American favorites

Amenities: The Naked Experience bedding

Pet-Friendly: Pineapple Pup Package available

Must-do experiences

  • Visit the Isabella Stewart Gardner Museum for stunning art and architecture.
  • Savor the lobster roll at James Hook & Co. for a local seafood delight.
  • Stroll through the Boston Public Market for fresh, local produce.
  • Take in a Red Sox game at Fenway Park for a classic Boston experience.
  • Explore the historic North End and enjoy authentic Italian pastries.
View all

Select your room type

Choose from doubles, suites, or family rooms, many with breakfast, flexible cancellation, and promotional rates
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

Boutique hotels design their amenities with your relaxation and unique travel experiences in mind

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 options invite guests to indulge in modern American cuisine in a lively atmosphere. Enjoy flavorful dishes and locally inspired choices that celebrate the vibrant culinary scene of Boston's charming South End.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American
Ambiance
A modern and stylish setting perfect for relaxation after a day of exploration, the Trophy Room features sleek decor and a welcoming vibe.
Key Offerings
Signature menu highlights include scrumptious avocado toast paired with braised tomatoes and goat cheese, making it a perfect stop for brunch or dinner with friends.
Reservation
Recommended
Wednesday to Saturday from 4:00 PM to midnight, 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
Local Highlights
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
America's oldest public park features expansive lawns and walking trails, perfect for a leisurely stroll or a picnic.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
One of the largest art museums in the US, showcasing impressive collections and special exhibitions throughout the year.
Fenway Park
Fenway Park
25 minutes' walk
Home of the Boston Red Sox, this iconic baseball park offers guided tours and thrilling game-day experiences.
New England Aquarium
New England Aquarium
25 minutes' walk
A marine exhibit featuring sea turtles, penguins, and IMAX films; great for families looking for fun and education.
Freedom Trail Walk
30 minutes' walk
The 2.5-mile historic trail connects 16 significant sites; ideal for history buffs and casual walkers alike.
Bike Rentals at Charles River
15 minutes' walk
Explore scenic views with bike rentals along the Charles River; a relaxing way to enjoy the outdoors.
Yoga in the Park
15 minutes' walk
Morning yoga sessions at Boston Common offer serenity and relaxation amidst beautiful natural surroundings.
Kayaking the Charles River
15 minutes' drive
Adventurous kayaking experience on the Charles River, providing stunning urban panoramas; seasonal availability.
The Trophy Room
The Trophy Room
1 minute' walk
An upscale eatery with a casual atmosphere; try their famous burgers and innovative cocktails.
Masa
Masa
3 minutes' walk
Southwestern-inspired cuisine in a vibrant space, famous for its excellent brunch and flavorful entrees.
Wink & Nod
Wink & Nod
2 minutes' walk
A creative cocktail bar known for its unique small plates and inventive drinks; reservations suggested.
Cosmica
Cosmica
2 minutes' walk
A warm atmosphere featuring traditional Mexican fare prepared with locally sourced ingredients; vegetarian options available.
Laugh Boston
15 minutes' walk
A comedy club featuring local and national talents; great for a night of laughs with friends or family.
Scullers Jazz Club
10 minutes' drive
Renowned for its live jazz performances and intimate setting; a perfect spot for music lovers.
Berklee Performance Center
10 minutes' drive
A vibrant venue hosting concerts and performances by talented students and renowned artists; family-friendly events available.
The Castle at Park Plaza
15 minutes' walk
Showcases various performances including theater and live music; a unique venue for a memorable night out.
Getting around
City Centre
Boston20 min  ·  1.6 km
Airports
Logan (BOS)13 min  ·  8.6 km
Worcester Regional (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
Looking for special rates when booking early?
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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 at 16:00 and check-out is by 12:00.
What nearby restaurants can guests find around Staypineapple, A Delightful Hotel, South End?
Nearby restaurants include Grill 23 & Bar (0.5 km), Masa (0.5 km), and The Friendly Toast (0.5 km).
What facilities are available for guests at Staypineapple, A Delightful Hotel, South End?
Facilities include free Wi-Fi, a bar/lounge area, an on-site restaurant, and a coffee station.
What amenities are provided in the rooms at Staypineapple, A Delightful Hotel, South End?
Rooms feature air conditioning, a flat-screen TV, a coffee maker, and designer bath products.
Does Staypineapple, A Delightful Hotel, South End offer bicycle rentals?
Bicycles are available for guest use at the hotel.
How far is Staypineapple, A Delightful Hotel, South End from the Museum of Fine Arts?
The museum is located 1 km from the hotel.
What dining options does Staypineapple, A Delightful Hotel, South End have?
The hotel features an on-site restaurant, Trophy Room, serving a variety of American dishes.
What types of breakfast are available at Staypineapple, A Delightful Hotel, South End?
Guests can enjoy breakfast items at the adjacent Berkeley Perk Café, including options such as breakfast tacos and omelettes.
What are the nearby attractions to Staypineapple, A Delightful Hotel, South End?
Nearby attractions include Fenway Park (2 km), the scenic Back Bay area (1 km), and the Freedom Trail (1 km).

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