Loved by Staypineapple, A Delightful Hotel, South End guests
Clean rooms
Friendly staff
Refillable water bottle
Convenient location
"Loved the filtered water and sparkling water on tap in the lobby."
Michael from United States
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"The bed was very large with separate duvets for each person."
Gary_Faulkner from Greece
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"The loaner bikes are a nice touch and come in handy for a quick ride along the River Charles."
Lisa from United States
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“Staypineapple charms with its playful pineapple theme and thoughtful perks like complimentary bikes; its location on the Back Bay-South End border puts much of Boston within easy reach. I especially appreciate the pet-friendly vibe and the unique 'Naked Experience' bedding, promising a cozy night's sleep. It's a fun, well-situated base for exploring the city.”
James DavidEditor-in-Chief at Dogfriendly-hotels
Select your room type
The hotel provides many room choices—family rooms, doubles, and pet-friendly suites—with breakfast, free cancellation, and special offers
South End Corner King
2 persons
18 m²
1 King-size bed
Coffee machine
Shower
room details
Back Bay King
2 persons
18 m²
1 King-size bed
Coffee machine
Shower
room details
Rates & availability calendar
See current prices and availability for your chosen dates!
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Check-in/ Check-out
Facilities
Hotels feature amenities designed to keep both you and your pet comfortable
Facilities: Great
8.3/10Review 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
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Dining Onsite
At Staypineapple, A Delightful Hotel, South End, dining is a charming exploration of modern American flavors. Guests can indulge in a vibrant atmosphere with locally-inspired dishes and the warmth of the South End neighborhood, making every meal a memorable experience.
Trophy Room
American
Ambiance
Modern and inviting, the Trophy Room features a cheerful atmosphere with a contemporary design, perfect for both casual gatherings and intimate dinners.
Key Offerings
Discover a delightful array of offerings, including a standout avocado toast topped with braised tomatoes and goat cheese, ideal for brunch or dinner alongside a selection of craft cocktails.
The oldest city park in the U.S., featuring expansive green spaces, walking paths, and historical monuments.
Boston Public Garden
15 minutes' walk
Famous for its swan boats and vibrant flowerbeds, this tranquil garden offers picturesque views and relaxation spots.
Museum of Fine Arts
25 minutes' walk
Home to a vast collection of artistic masterpieces, with free admission days available for visitors. Worth a visit.
Freedom Trail
16 minutes' walk
A 2.5-mile-long path through historic Boston, featuring 16 significant sites that tell America's Revolutionary history.
Biking along the Charles River
10 minutes' drive
Scenic biking paths perfect for all levels. Rentals available nearby. Ideal for active travelers.
Yoga at Boston Common
15 minutes' walk
Outdoor yoga sessions provide relaxation amidst nature. Check seasonal schedules for classes.
Visit Newbury Street
15 minutes' walk
Shopping and culture merged on this famous street, featuring boutique stores and coffee shops.
The Trophy Room
1 minute' walk
Casual eatery with an eclectic menu. Famous for its burgers and craft cocktails. Reservations recommended.
Masa
3 minutes' walk
New Mexican cuisine in a vibrant setting. Signature dishes include enchiladas and tacos. Great for families.
Wink & Nod
2 minutes' walk
Innovative cocktails and unique dishes in a cozy vibe. Ideal for couples' nights out. Reservations suggested.
The Wilbur Theatre
10 minutes' drive
A historic venue hosting live performances, including comedy shows and concerts. Check the schedule for events.
House of Blues
15 minutes' drive
Famous music venue featuring a vibrant nightlife atmosphere with live bands. Great for music lovers.
Laugh Boston
10 minutes' drive
Comedy club offering stand-up performances. Perfect for a fun night out with friends, suitable for all ages.
Local transport and travel tips
City Centre
Boston 20 min · 1.6 km
Airports
Logan (BOS) 13 min · 8.6 km
Worcester Regional (ORH) 116 min · 76.7 km
Train
Boston South Station 17 min · 1.4 km
Underground
Back Bay Metro Station 5 min · 400 m
Bus
Bus stop 2 min · 100 m
Want access to early-bird pet-friendly hotel deals?
Access exclusive discounts today!
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 the entire hotel 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, is praised for its convenient location near attractions like Fenway Park, The Newbury, and The Prudential, placing guests within easy walking distance of the best Boston has to offer. The hotel's charming pineapple decor has been noted, and some guests appreciated the provided reusable water bottle and the option to refill it. While the rooms are often described as compact, the well-thought-out layout and comfortable beds are commonly appreciated. A few guests have mentioned the small size of the bathrooms.
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Review score
Based on 732 verified reviews
8.6 /10
Great
84 %
Recommend
Location
9.1/10
Staff
9.1/10
Free WiFi
7.4/10
Value for money
8.1/10
Pros
Clean rooms
Comfortable beds
Good location
Friendly staff
Free drink
Cons
Non-working TV
Guest reviews
based on 732 reviews
8.6/10
based on 61 reviews
3.5/5
based on 867 reviews
8.5/10
Michael from United Kingdom
Couple
Back Bay King
4 nights in November 2025
|
Reviewed: January 27, 2026
7/10
helpful staff bag storage small rooms noisy window
The bar onsite provided food. This was really nice. We had food there on a rainy night, so we didn't have to go out. The front desk staff was helpful. They answered all my questions. They allow you to store your bags if you arrive early. I would stay there again.
Rooms at this hotel are very small, and that includes the bathroom. I found my room quite noisy. The window did not close properly. It didn't lock. I could hear the train all hours.
0 Helpful
William from United Kingdom
Family with children
south end corner king
3 nights in November 2025
|
Reviewed: January 12, 2026
6/10
cramped room outside noise
the location was acceptable for my needs, close to public transport.
I was disappointed by the room size. It felt cramped and barely had space to move around. also, the noise from outside was a constant annoyance. I could hear street traffic all night. the window seemed to offer little sound insulation. I expected better for the price.
0 Helpful
Riley from Australia
Couple
South End Corner King
3 nights in November 2025
|
Reviewed: December 22, 2025
7/10
helpful staff spacious shower comfy bed old air conditioning undone stitching snapped whiskers
this place did impress. the staff was friendly and helpful, always willing to help with directions. i loved that the room had a large, spacious shower. the bed was super comfy, i slept soundly.
our air conditioning was very old. i found it difficult to use without a rattling sound. our dash, the dog, stitching was coming undone at his belly. i noticed his whiskers were snapped.
0 Helpful
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FAQs
About Staypineapple, A Delightful Hotel, South End
What time is check-in and check-out at Staypineapple, A Delightful Hotel, South End?
Check-in is from 16:00 and check-out is by 12:00.
How far is Staypineapple, A Delightful Hotel, South End from Boston Logan International Airport?
The hotel is approximately 7 km from Boston Logan International Airport, which takes about 15 minutes by car.
What dining options are available at Staypineapple, A Delightful Hotel, South End?
The on-site Trophy Room offers a lively dining scene with an all-American menu.
Are there any notable attractions near Staypineapple, A Delightful Hotel, South End?
Nearby attractions include Fenway Park (1 km), Museum of Fine Arts (2 km), and the Freedom Trail (1 km).
Does Staypineapple, A Delightful Hotel, South End offer parking facilities?
The hotel provides limited on-site parking for a fee.
What amenities can guests expect in the rooms at Staypineapple, A Delightful Hotel, South End?
Rooms feature a flat-screen TV, free Wi-Fi, air conditioning, a work desk, and upscale designer bath products.
Does Staypineapple, A Delightful Hotel, South End provide any business services?
The hotel has a 24-hour front desk and offers free Wi-Fi throughout the property.
Are there recreational activities available at Staypineapple, A Delightful Hotel, South End?
Guests can use the complimentary bicycles provided by the hotel to explore the city.