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Staypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photo

Staypineapple, A Delightful Hotel, South End

•
8.4|Great
Check rooms and rates
From$97 /nightOnly on Our Website-10%
Check-in
26Oct
Check-out
27Oct
Guests
2 Guests
Key details

About the Hotel

26 Chandler St, Boston, 02116
-
Close to Copley Square
Great
8.4
9.0
/10
4.2
4.3
/5

Boutique hotel in Boston's South End with the exclusive Naked Experience bedding

Amenities

Staypineapple, A Delightful Hotel, South End offers the exclusive Naked Experience, which uses European-style individual duvets on each side of the bed for guest comfort. Each room includes a flat-screen TV with streaming capabilities and a walk-in marble shower in the private bathroom. The daily Amenity Fee covers high-speed Wi-Fi, a reusable water bottle with access to the Water Bar, and two complimentary drinks at the on-site Trophy Room bar.

Dining

The on-site Trophy Room serves an all-American menu in a lively setting that is open to the public. Guests receive two complimentary drink vouchers at check-in that can be redeemed at the Trophy Room bar. The hotel also offers Daily Afternoon Delights, which feature signature pineapple treats and coffee, available each afternoon.

Location

The hotel sits on the border of Back Bay and South End, within walking distance to Fenway Park and the shops of Back Bay station. Guests can borrow one of the complimentary bicycles to explore the city, including nearby attractions like the Boston Center for the Arts. The scenic Newbury Street with its gourmet restaurants is a 10-minute walk from the property.

Services

Staypineapple is a pet-friendly hotel with specialized dog amenities, including a pet basket and pet bowls provided at the hotel. The hotel covers a daily Amenity Fee that includes services for pets traveling with guests. There is no weight limit or breed restriction for dogs staying at the property.

Highlights

Bedding: Naked Experience with individual duvets

Location: Back Bay and South End border

Dining: Trophy Room with all-American menu

Perks: Complimentary bikes & daily pineapple treats

Extra: No dog weight or breed restrictions

“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.”
Hotel logo
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
Back Bay King
2 persons
18 m²
1 King-size bed
Coffee machine
Shower
South End Corner King
2 persons
18 m²
1 King-size bed
Coffee machine
Shower

Rates & availability calendar

See current prices and availability for your chosen dates!

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

Guest Parking

  • No parking available.

Services

  • Pet amenities available

Dining

  • Restaurant
  • Bar/ Lounge area

Room features

  • Air conditioning
  • Heating
  • Tea and coffee 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.
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 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.
Reservation
Reservations are recommended.
Wednesday to Saturday: 4:00 PM - 12:00 AM, Sunday: 12:00 PM - 8:00 PM

Location

26 Chandler St, Boston, 02116
Map view
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 South End
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
Boston Common
15 minutes' walk
The oldest city park in the U.S., featuring expansive green spaces, walking paths, and historical monuments.
Boston Public Garden
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
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
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
The Trophy Room
1 minute' walk
Casual eatery with an eclectic menu. Famous for its burgers and craft cocktails. Reservations recommended.
Masa
Masa
3 minutes' walk
New Mexican cuisine in a vibrant setting. Signature dishes include enchiladas and tacos. Great for families.
Wink & Nod
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 3 verified reviews
6.7 /10
Nice
100%
Recommend
Staff
9.1/10
Location
9.0/10
Free Wi-Fi
7.7/10
Value for money
7.9/10
Pros
Clean rooms
Comfortable beds
Good location
Friendly staff
Free drink
Cons
Non-working TV
Guest reviews
based on 3 reviews
6.7/10
based on 61 reviews
3.5/5
based on 811 reviews
8.4/10
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
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.

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