Is there a parking facility near the hotel and what is the charge?
15 November 2024
A garage is available nearby at 100 Clarendon Street for a nightly rate of $36.
74 photos
STAYPINEAPPLE, A DELIGHTFUL HOTEL, SOUTH END, Boston – A Smart Stay in the City
97US$
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Key details
About the Hotel
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
- Close to Copley Square
Great
8.5
9.0
4.1
4.2
Loved by Staypineapple, A Delightful Hotel, South End guests
"The bed was very large with separate duvets for each person."
"The hotel offers free coffee and biscuits daily between certain times..."
"Room decor is really cute."
Rooms & Amenities
Staypineapple Boston offers rooms with plush pillow-top beds, European-style double duvets, and high-speed Wi-Fi. Each room includes a Keurig coffee maker, flat-screen TV with streaming, and marble-tiled bathrooms with walk-in showers. The South End Corner King provides extra natural light and partial city views.
Dining & Drinks
The Trophy Room serves American classics, including the Chandler Street Burger and signature cocktails like the Trophy Wife (vodka with passion fruit and elderflower). The adjacent Berkeley Perk Café offers breakfast tacos and omelets. A self-service coffee station and pineapple treats are available in the lobby.
Leisure & Activities
Guests can borrow yellow beach cruisers to explore Boston. The Trophy Room hosts trivia nights and weekend breakfast with live performances. Afternoon coffee and pineapple treats are served daily from 3:30 PM to 6:30 PM.
Location & Access
The hotel is on the border of Back Bay and South End, 400 m from Back Bay Station and 550 m from Arlington Station (Green Line). Fenway Park is a 10-minute train ride away. Nearby attractions include the Freedom Trail (1 km) and Copley Square (0.5 km).
Guest Services
Services include 24-hour front desk assistance, free Wi-Fi, and reusable water bottles with refill stations. Dog-friendly rooms come with a bed, treats, and a collapsible bowl. The Everything Button connects guests to additional requests like extra coffee or dining recommendations.
Must-do experiences
- Visit the Boston Public Market for fresh, local food delights.
- Stroll through the beautiful Boston Common, the oldest park in the U.S.
- Savor the famous North End cannoli at Mike's Pastry; it's a must-try!
- Explore the hidden murals of the South End's SoWa Art District.
- Catch a game at Fenway Park, home to the iconic Boston Red Sox.
View all
Choose the Room
From cosy doubles to spacious family suites – all with flexible options, breakfast, and exclusive deals.
South End Corner King
2 persons
195 sq. feet
1 King-size bed
Shower
Coffee machine
room details
Back Bay King
2 persons
195 sq. feet
1 King-size bed
Shower
Coffee machine
room details
Check Dates & Room Rates
See what's available for your travel dates
Amenities
Thoughtfully designed amenities for a comfortable & memorable stay
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
Trophy Room offers a delightful American dining experience set in a modern and inviting atmosphere. With a menu that highlights local flavors, this vibrant restaurant invites guests to indulge in thoughtfully prepared brunch and dinner options, all just a stone's throw from the charming South End neighborhood.
Staypineapple, A Delightful Hotel, South End Location
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
Map view
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
City landmarks
Stadium
Fenway Park
1.4
mi
Landmark
Boston Common
3900 ft
Market
Faneuil Hall Marketplace
1.4
mi
Park
Boston Public Garden
4100 ft
Landmark
Freedom Trail
4200 ft
Museum
Museum of Fine Arts
1.3
mi
Aquarium
New England Aquarium
1.4
mi
Museum
Museum of Science
1.4
mi
Museum
Boston Tea Party Ships & Museum
1.3
mi
Library
Boston Public Library
2900 ft
Parking area
Skywalk Observatory
3700 ft
Square
Copley Square
2600 ft
Landmark
North End
1.5
mi
Landmark
Freedom Trail walk
1.6
mi
Spa Centre
Newbury Street
3900 ft
Church
Trinity Church
2200 ft
Landmark
Boston Children's Museum
1.5
mi
Cemetery
Granary Burying Ground
5100 ft
Monument
Bunker Hill Monument
2.1
mi
Museum
Isabella Stewart Gardner Museum
1.6
mi
Landmark
Beacon Hill
1.2
mi
Monument
New England Holocaust Memorial
1.3
mi
Museum
The Paul Revere House
1.4
mi
Tower
John Hancock Tower
2100 ft
Landmark
Quincy Market
1.3
mi
Museum
USS Constitution Museum
2.0
mi
Museum
The Institute of Contemporary Art
1.5
mi
Public Building
Old State House
1.2
mi
Theatre
Boston Symphony Hall
5100 ft
Landmark
Back Bay
3100 ft
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
Local Highlights
Boston Common
15 minutes' walk
The oldest public park in the U.S., featuring scenic pathways, open lawns, and seasonal events, including free concerts.
Fenway Park
25 minutes' walk
Home of the Boston Red Sox, this historic baseball stadium offers guided tours and an iconic atmosphere on game days.
Boston Public Garden
15 minutes' walk
Famous for its swan boats and beautiful landscapes, this botanical garden is perfect for a peaceful stroll or picnic.
Freedom Trail
16 minutes' walk
A 2.5-mile route showcasing Boston's historic sites, perfect for history buffs and those interested in colonial heritage.
The Trophy Room
1 minute' walk
Casual eatery known for its creative cocktails and modern American fare, with a warm atmosphere for gatherings.
Masa
3 minutes' walk
Vibrant southwestern cuisine with a lively atmosphere; try their signature mole dish and innovative margaritas.
Getting around
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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
Guest Ratings & Reviews
Real Guest Experiences & Ratings
Show moreShow less
Pros
Friendly staff
Pineapple decor
Cool blankets
Good quality TV
Excellent location
Cons
Small rooms
Mandatory fee
Old elevators
Plumbing issues
Guest reviewsbased on 923 reviews
Nathaniel from United Kingdom
Single
Back Bay King
3 nights in November 2025
|
Reviewed: January 17, 2026
6/10
small roommissing closet
the room size proved inadequate. space for luggage was almost non-existent and movement was difficult. the lack of a proper closet compounded this issue, reducing the comfort i expect.
0 Helpful
Joseph from Canada
Single
Back Bay King
3 nights in November 2025
|
Reviewed: December 22, 2025
9.5/10
cozy stay
pineapple themeclean roomfun staffmusty odor
i loved the pineapple theme. the hotel was very clean and fresh. the staff was courteous and fun. i found the pineapple accents everywhere very charming.
the bathroom was very small. it also had a musty odor. i hope they address this in the future.
Location
9/10
the hotel is within easy walking distance of many restaurants. this made dining options very convenient. i also appreciated the proximity to shops and other local attractions.
Service
10/10
the front desk staff was excellent. they were attentive and quick to respond to requests. i was particularly impressed with how they handled a minor issue with my room key.
0 Helpful
|
Owen from United Kingdom
Business traveller
South End Corner King
3 nights in November 2025
|
Reviewed: December 05, 2025
9/10
quirky and fun!
tin bottlesearly checkdog adoptionconvenient location
The hotel gave tin bottles of water. They had a pineapple logo on them. i got an early check-in, a nice surprise! the hotel promotes dog adoption (i really like this). the location is convenient. I walked to see the city easily.
the bar downstairs sometimes gets noisy.
Facilities
9/10
The hotel offers complimentary bicycle rentals . This made exploring the area fun. (i biked to the local park.) the bar provides a space for relaxation with a complimentary drink upon arrival.
0 Helpful
|
Harper from United States
Single
Back Bay King
4 nights in August 2025
|
Reviewed: October 02, 2025
9.0/10
Good Amenities
unique themecomfortable beddingrelaxing robes
i enjoyed the hotel's theme embedded throughout. the bedding felt comfortable, and robes were available in the room. i liked the thoughtful addition of the naked experience theme, which promotes a feeling of freedom and relaxation .
the parking garage had a high nightly rate.
Service
9/10
the staff ensured guests felt comfortable and welcome. katherine w, alongside david, provided nice assistance. i found the team helpful .
Facilities
8/10
a free metal water bottle was provided, alongside a fresh water machine in reception. the facility offers chilled and sparkling water. free coffee was available all day, which i found convenient .
Rooms
10/10
the room included two duvets, so guests no longer have to compete for their half. the coffee maker was supplied with tea pods. it was advantageous for tea drinkers. the provided silky robes felt quite luxurious.
0 Helpful
|
janet from united kingdom
south end corner king
3 nights in June 2025
|
Reviewed: July 24, 2025
7/10
perfect locationfriendly staffhelpful staffmissing closetsmall deskmissing refrigerator
the location was really perfect. it allowed me to easily visit nearby places and explore the charming streets. i loved that the hotel has a fun theme. the energy of the place was so lovely. the staff was very helpful and friendly.
The hotel room lacked a closet. It made organizing my belongings a little difficult. there was also no refrigerator in the room. i missed having a place to store snacks and drinks. the desk wasn't a real desk it was small. it made working difficult.
0 Helpful
Questions of the users
About Staypineapple, A Delightful Hotel, South End
Are there options for guests to leave their bags before check-in or after check-out?
20 December 2024
There is a secure area for guests to store their luggage both before checking in and after checking out.
Could you describe what guests can expect from the Naked Experience?
10 October 2024
The Naked Experience promises a cozy and luxurious night's sleep with freshly laundered linens, featuring two cloud-like duvets for ultimate comfort.
Is high-speed Wi-Fi accessible in all guest rooms?
5 January 2025
Wi-Fi is available throughout the property, including all guest rooms, ensuring connectivity during your stay.
Can guests bring their pets, and if so, are there any fees involved?
25 February 2025
The hotel is dog-friendly with a nightly pet fee of $25, which covers essentials like a dog bed and treats.
What breakfast options are available for guests during their stay?
3 March 2025
Currently, the hotel does not offer a continental breakfast, but there are several nearby restaurants that serve breakfast.
What is the recommended method for traveling to the airport from the hotel?
17 November 2024
Ride-share services such as Uber or Lyft are the most convenient options for getting to the airport from the hotel.
Are coffee machines available in the rooms, and do they provide hot water?
28 April 2025
Each room is equipped with Keurig machines that can dispense hot water, perfect for tea or other beverages.
Is it possible to add a guest's name to an existing reservation?
4 June 2025
Yes, it's possible to add a name to a reservation at the hotel.
Are there nearby attractions to explore while staying at the hotel?
12 September 2025
The hotel is located in the heart of the historic South End, close to unique boutiques, trendy restaurants, and cultural sites.
Can guests enjoy in-room refreshments during their stay?
19 January 2025
In-room coffee and tea are provided through Keurig machines, with additional options available upon request.Next best alternative
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