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From97US$ /night
Check-in
26Mar2026Select date
Check-out
27Mar2026Select 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
8.5
9.0
/10
4.2
4.2
/5

Rooms: Naked Experience

Staypineapple Boston rooms feature plush pillow top beds, European-style double duvets as part of the signature Naked Experience, high-speed Wi-Fi, and bath products. Each room includes a flat-screen TV and iPod docking station. Guests have a choice of coffee or tea for the in-room Keurig. The yellow bedside shelf tables have charging points. The Back Bay King has a king bed and a walk-in shower. The South End Corner King provides more light and quiet.

Options for dining

The Trophy Room, the hotel's restaurant, features a long room lined with windows overlooking the street, serving American cuisine. The menu includes avocado toast with braised tomatoes and goat cheese. The bar is open until 2 AM and serves cocktails. The adjacent Berkeley Perk Café serves breakfast tacos and omelettes. Afternoon delights include coffee and pineapple treats in the lobby from 3:30 PM to 6:30 PM.

Leisure and Activities

Guests have access to beach cruisers for city exploration. The hotel provides high-speed wireless Internet. The lobby offers help-yourself coffee. Guests can purchase snacks, beer, wine, and other refreshments. The hotel is near the summer-to-December SoWa Open Market and SoWa First Fridays.

Location and transport

Staypineapple Boston is in Downtown Boston on the border of Back Bay and South End. It is near Freedom Trail sites, the Financial District, and City Hall. The hotel is near Tony's Pizza, The Coffee Bean, and Urban Outfitters. It is a 10-minute walk to Arlington Station for trains to Fenway Park. The hotel is near the Boston Public Library, Boston Public Garden, and Newbury Street.

Services and amenities

The hotel provides PATH water bottles. There is a water bar in the lobby. Pineapple bikes are available for guest use. A work desk and telephone with access to the 24-hour front desk are provided. The hotel is dog-friendly. There are pineapple treats and coffee. There are charging points.

“In Boston's South End, this hotel stands out with its friendly environment and convenient access to key spots like the Public Garden and Back Bay Station. The rooms are noted for comfort and cleanliness. I especially appreciate that the hotel welcomes dogs and offers perks like complimentary drinks upon arrival.”
Hotel logo
James DavidEditor-in-Chief at Airporthotel
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Select your room type

The hotel offers rooms of different types and facilities suitable for every traveler
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

Airport hotels designed with facilities that ensure convenience and comfort
Facilities: Great
8.4/10Review score

General

  • No smoking on site
  • 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

Experience the vibrant culinary offerings at Staypineapple, A Delightful Hotel, South End, where local flavors meet inviting atmospheres. The onsite dining options reflect a modern take on American cuisine, providing a delightful retreat for travelers looking to indulge in tasty meals without venturing far from the hotel's charm.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American cuisine with a modern twist
Ambiance
A contemporary space filled with light and energy, suitable for both casual gatherings and festive dinners.
Key Offerings
Signature dishes include avocado toast topped with braised tomatoes and goat cheese, perfect for brunch or a lively dinner experience.
Reservation
Recommended for dinner.
Brunch on Sundays from 12:00 - 20:00; Dinner from Wednesday to Saturday, 16:00 - 00:00.

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
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
15 minutes' walk
The oldest city park in the US, featuring beautiful landscapes, walking paths, and seasonal events.
Freedom Trail
16 minutes' walk
A historic 2.5-mile trail showcasing 16 significant sites, including museums and landmarks.
Museum of Fine Arts
25 minutes' walk
Home to an impressive collection of artwork from around the world, with various exhibitions year-round.
Biking along the Charles River Esplanade
15 minutes' walk
Scenic paths ideal for biking, running, or walking with rental services available along the route.
Wellness at Exhale Spa
10 minutes' walk
Relaxation-oriented spa offering yoga, fitness classes, and rejuvenating treatments in a serene environment.
The Trophy Room
1 minute' walk
Casual American eatery known for its burgers and craft beers, featuring a cozy atmosphere and friendly service.
Masa
3 minutes' walk
Southwestern-inspired menu featuring fresh ingredients and a vibrant setting, great for group dining.
Wink & Nod
2 minutes' walk
Innovative cocktails and globally inspired dishes in a stylish, hidden gem ambiance; reservations recommended.
The Wilbur Theatre
15 minutes' walk
Historic venue hosting concerts, comedy shows, and live performances in an elegant setting.
Lansdowne Street
25 minutes' walk
Nightlife spot with various bars and clubs, offering a lively atmosphere perfect for groups and nightlife enthusiasts.
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
Wireless 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
Property is also known as
staypineapple boston
staypineapple a delightful hotel south end boston

Reviews and Ratings

Feedback about Staypineapple, A Delightful Hotel, South End from previous guests about their experience.
Review score
Based on 692 verified reviews
8.5/10
Great
85%
Recommend
Cleanliness
8.8/10
Comfort
8.8/10
Facilities
8.4/10
Free Wi-Fi
7.6/10
Location
9.1/10
Staff
9.1/10
Value for money
8.1/10
Pros
Clean room
Reusable bottle
Good beds
Cons
Inexperienced staff
Small rooms
Guest reviews
based on 61 reviews
3.5/5
based on 930 reviews
8.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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Questions of the users
About Staypineapple, A Delightful Hotel, South End
Is there a nearby parking facility, and what are the costs associated with it?
15 November 2024
There is a garage located at 100 Clarendon Street, which charges $36 per night for parking.
What is the name of the parking garage close to the hotel?
20 December 2024
The nearby parking facility is called Clarendon Garage.
Can guests leave their luggage at the hotel before check-in or after check-out?
5 February 2025
A secure luggage deposit service is available for guests to store their bags before check-in and after check-out.
Does the hotel have elevators to access different floors?
12 January 2025
Yes, the hotel is equipped with elevators for guest convenience.
What is included in the Naked Experience that your hotel offers?
3 March 2025
The Naked Experience features cozy, freshly laundered bedding with cloud-like European-style duvets, along with a luxurious stay designed for ultimate comfort.
Is Wi-Fi available throughout the hotel and in guest rooms?
10 April 2025
High-speed Wi-Fi is available throughout the property, including in every guest room.
Are pets welcome at the hotel, and what are the fees?
25 January 2025
Pets are allowed, and there is a nightly pet fee of $25, plus tax, which includes amenities for your dog.
What are the breakfast options available at the hotel?
14 February 2025
Currently, there is no continental breakfast offered as the onsite restaurant is closed; however, several nearby restaurants serve breakfast.
What transportation service is recommended for reaching the airport from the hotel?
22 March 2025
Ride-share services like Uber or Lyft are recommended for easy transportation to the airport.
Are there any facilities for brewing hot drinks like tea or coffee in the room?
6 April 2025
Each room is equipped with a Keurig coffee machine which can provide hot water for herbal tea as well.

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