STAYPINEAPPLE, A DELIGHTFUL HOTEL, SOUTH END, Boston
97US$
Book on our site
for up to 10% off
than to Booking.com!
Key details
Hotel Details
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
-
Near the Freedom Trail
Great
8.5
9.0
/10
4.1
4.2
/5
Loved by Staypineapple, A Delightful Hotel, South End guests
Kind staff
Free welcome drink
Well-decorated rooms
Plush towels
Excellent shower pressure
Perfect location
"The bed was very large with separate duvets for each person."
Gary_Faulkner from United Kingdom
read full review
"Loved the dogs!!"
Suleyma from United States
read full review
"All guests get a free drink when they check in!"
Ty from United States
read full review
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
“Located where South End meets Back Bay, this boutique hotel stands out with its playful pineapple theme and genuinely vintage details. The Naked Experience bedding promises comfort, while complimentary bikes add an element of fun, casual exploration to the Boston visit. The on-site Trophy Room ensures a lively dining scene, making this a practical choice for those who appreciate character.”
Charlotte EvansHead of Editorial at Hotelsdowntown
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
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 Availability & Prices
Find the best rates for your travel dates now!
Facilities
Hotel has comfortable rooms, premium services, and a prime downtown location
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
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.
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.
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
Spa Centre
Newbury Street
3900 ft
Landmark
Freedom Trail walk
1.6
mi
Church
Trinity Church
2200 ft
Cemetery
Granary Burying Ground
5100 ft
Landmark
Boston Children's Museum
1.5
mi
Tower
John Hancock Tower
2100 ft
Monument
New England Holocaust Memorial
1.3
mi
Monument
Bunker Hill Monument
2.1
mi
Museum
The Paul Revere House
1.4
mi
Landmark
Beacon Hill
1.2
mi
Museum
Isabella Stewart Gardner Museum
1.6
mi
Landmark
Quincy Market
1.3
mi
Museum
The Institute of Contemporary Art
1.5
mi
Public Building
Old State House
1.2
mi
Museum
USS Constitution Museum
2.0
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
Explore the South End
Top Attractions
Activities
Dining
Entertainment
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
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
25 minutes' walk
A bustling market with shops, eateries, and street performances, perfect for experiencing Boston's vibrant culture and history.
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
1 minute' walk
An inviting bar and restaurant featuring American comfort food and craft cocktails, perfect for a relaxed evening out.
Masa
3 minutes' walk
Serving inventive Southwestern fare, this lively spot offers a vibrant atmosphere with a blend of delicious flavors.
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
·
1.0
mi
Airports
Logan (BOS)13 min
·
5.3
mi
Worcester Regional (ORH)116 min
·
47.7
mi
Train
Boston South Station17 min
·
4600 ft
Underground
Back Bay Metro Station5 min
·
1400 ft
Bus
Bus stop2 min
·
400 ft
Unlock Exclusive Early Booking Rates
Plan ahead and get special discounts now!
Check Rates
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
Reviews and Ratings
Feedback about Staypineapple, A Delightful Hotel, South End from previous guests about their experience.
Review summary
Based on recent reviews
Powered by AI
Staypineapple, A Delightful Hotel, South End charms guests with its pineapple-themed decor and generally cozy atmosphere. Its South End location makes Boston Common easily walkable, and many appreciate being close to restaurants and the chic South End business district. Some guests have found the rooms compact, but love the comfy beds and spa robes. Guests also love the availability of free water refills and the option to adopt a stuffed husky, supporting animal rescue.
Show moreShow less
Review score
Based on 701 verified reviews
8.5/10
Great
84%
Recommend
Location
9.1/10
Staff
9.1/10
Free Wi-Fi
7.3/10
Breakfast
7.5/10
Pros
Comfortable bed
Friendly staff
Perfect location
Cons
Tiny rooms
Plumbing issues
Guest reviews
based on 61 reviews
3.5/5
based on 893 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.
Open reviews
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.