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From97US$ /night
Check-in
07Dec2025Select date
Check-out
08Dec2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Details

26 Chandler St, Boston, Massachusetts, United States, 02116
-
Near the Freedom Trail
Perfect
8.4
9.0
/10
4.1
4.3
/5

Staypineapple, A Delightful Hotel, South End - A boutique Boston hotel with European-style bedding, on-site dining, and arts district location

Located in the charming South End neighborhood, this 4-star Boston hotel features The Naked Experience bedding system with cloud-like European-style individual duvets and plush pillow-top mattresses. The Trophy Room restaurant and bar serves American classics until 2 AM, offering signature cocktails like the Trophy Wife with passion fruit and elderflower-laced vodka. Each room comes equipped with a flat-screen TV, iPod docking station, Keurig coffee maker, and designer bath products. Staypineapple provides complimentary bikes for city exploration and hosts daily afternoon treats with coffee in the lobby. The Berkeley Perk Café serves breakfast items including tacos and omelets. The property features genuine vintage elements like the original black painted iron staircase. Staypineapple, A Delightful Hotel sits on the border of Back Bay and South End, within walking distance to the Freedom Trail and a direct train connection to Fenway Park.

Pros

Daily complimentary afternoon treats and coffee service from 3:30 PM to 6:30 PM

The Water Bar offers unlimited cold, hot, still, and sparkling water refills

Access to the summer-to-December SoWa Open Market and monthly SoWa First Fridays art market

Corner rooms feature additional natural light and partial city views

Cons

1 mile distance to New England Aquarium and Faneuil Hall Marketplace

Limited on-site breakfast options with only café service available

View all

Select room type

Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, 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
Bay view
Shower
Coffee machine

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Facilities

Hotel has comfortable rooms, premium services, and a prime downtown location

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, indulge in a culinary experience that embraces the heart of American fare. With a modern atmosphere and thoughtfully crafted dishes, dining here is a celebration of local flavors nestled in the vibrant 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 sleek decor that blends a contemporary feel with cozy intimacy, perfect for casual gatherings or special occasions.
Key Offerings
The menu highlights delicious choices like avocado toast with braised tomatoes and goat cheese, showcasing the best of local ingredients. The Trophy Room serves brunch and dinner, inviting guests to unwind with delightful meals as they soak in the lively atmosphere.
Reservation
Recommended
Brunch: Sunday 12:00 - 20:00; Dinner: Wednesday to Saturday 16:00 - 00:00.

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 the South End
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
The nation's oldest public park offers scenic paths, historic statues, and lush lawns ideal for relaxation and picnicking.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Home to an impressive collection of art from around the world, the museum hosts special exhibitions and free admission days.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
A bustling market with shops, eateries, and street performances, perfect for experiencing Boston's vibrant culture and history.
Freedom Trail
Freedom Trail
16 minutes' walk
A 2.5-mile long path dotted with historic sites, this iconic trail offers self-guided tours through Boston's revolutionary past.
Bike Rentals Along the Charles River
20 minutes' walk
Bike rental services near the Charles River provide stunning views and numerous trails for outdoor enthusiasts of all levels.
Spa Treatments at Bella Sante
15 minutes' walk
Indulge in exceptional spa services, offering massage therapies and skin treatments in a serene environment for relaxation.
The Trophy Room
The Trophy Room
1 minute' walk
An inviting bar and restaurant featuring American comfort food and craft cocktails, perfect for a relaxed evening out.
Masa
Masa
3 minutes' walk
Serving inventive Southwestern fare, this lively spot offers a vibrant atmosphere with a blend of delicious flavors.
Cosmica
Cosmica
2 minutes' walk
A contemporary eatery focusing on Mexican-inspired cuisine, known for its fresh ingredients and cozy ambiance.
Boston Symphony Orchestra
20 minutes' walk
World-renowned orchestra offering spectacular performances, from classical to contemporary, in a stunning concert hall.
The Wilbur Theatre
12 minutes' walk
Historic venue featuring a variety of entertainment from comedy shows to concerts, catering to diverse tastes and ages.
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
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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 are the check-in and check-out times at Staypineapple, A Delightful Hotel, South End?
Check-in is at 16:00 and check-out is by 12:00.
How far is Staypineapple, A Delightful Hotel, South End from Fenway Park?
The hotel is approximately 2 km from Fenway Park.
Are there dining options on-site at Staypineapple, A Delightful Hotel, South End?
The hotel features an on-site restaurant, Trophy Room, offering an all-American menu.
What room amenities are provided at Staypineapple, A Delightful Hotel, South End?
Rooms include air conditioning, a flat-screen TV, high-speed Wi-Fi, and designer bath products.
What nearby restaurants can guests find close to Staypineapple, A Delightful Hotel, South End?
Nearby restaurants include Berkeley Perk Café (0.5 km), Masa (0.5 km), and Grill 23 & Bar (0.5 km).
How does the hotel assist guests with local transportation needs at Staypineapple, A Delightful Hotel, South End?
Guests can rent bicycles at the hotel for convenient city exploration.
What is unique about the rooms at Staypineapple, A Delightful Hotel, South End?
The hotel features a unique Naked Experience with cloud-like European-style individual duvets.
What attractions are within walking distance of Staypineapple, A Delightful Hotel, South End?
The hotel is within walking distance to the Freedom Trail and the Back Bay area.

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