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, Boston

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From$97 /night
Check-in
01Sept
Check-out
02Sept
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview

26 Chandler St, Boston, 02116
-
Close to Copley Square
Great
8.5
9.0
/10
4.2
4.3
/5

Staypineapple, A Delightful Hotel, South End is a 4-star Boston hotel featuring stylish accommodations in the vibrant South End neighborhood. The hotel offers unique amenities such as The Naked Experience, a signature comfortable bedding concept, along with an on-site restaurant and bar.

Rooms & Amenities

Rooms at Staypineapple feature plush pillow top beds and are equipped with upscale amenities, including high-speed Wi-Fi and designer bath products. Each room also offers a flat-screen TV with streaming capability. The South End Corner King provides additional natural light and urban views for added comfort.

Dining & Options

Food and drink options include the Trophy Room, which serves an American menu with both brunch and dinner options, alongside craft cocktails. The Berkeley Perk Café offers breakfast choices like tacos and omelettes for a quick meal before exploring the city.

Leisure & Activities

Staypineapple facilitates leisure activities with complimentary bike rentals, providing easy access to nearby attractions such as Boston Common and the Museum of Fine Arts. The hotel also offers Afternoon Delights featuring coffee and signature pineapple treats in the lobby.

Services & Transportation

Business services are available with work desks in rooms and a 24-hour front desk for guest assistance. The hotel's central location provides quick access to the subway stations, with Arlington station just an 8-minute walk away for convenient transportation to city landmarks.

Must-do experiences

  • Take a stroll in the Boston Public Garden for serene landscapes.
  • Grab a lobster roll at Neptune Oyster in the North End.
  • Discover art at the Isabella Stewart Gardner Museum, a hidden gem.
  • Explore the vibrant stalls at the Boston Public Market for local goods.
  • Catch a Red Sox game at Fenway Park for a classic Boston experience.

Pick the Room That Suits Your Travel Needs

Rooms for singles, families, or groups—many with breakfast, free cancellation, and exclusive airport packages
South End Corner King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower
Back Bay King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower

View Room Rates & Availability by Date

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August 2026 - August 2027
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Check-in/ Check-out

Facilities

Comfortable Rooms and Convenient Services to Enhance Your Layover
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
Show more

Dining Onsite

At Staypineapple, A Delightful Hotel, South End, guests are invited to indulge in the vibrant dining experience at the Trophy Room. Serving modern American cuisine with a flair, this inviting spot offers a cozy atmosphere perfect for savoring brunch or dinner while enjoying the charm of the South End.
  • Trophy Room

    Modern American
    Ambiance
    A warm and contemporary setting featuring stylish decor, perfect for both intimate dinners and lively brunch gatherings.
    Key Offerings
    Delight in signature dishes such as avocado toast topped with braised tomatoes and goat cheese, complemented by a selection of refreshing beverages. The Trophy Room creates a welcoming atmosphere for relaxation after a day of exploration.
    Reservation
    Recommended
    Open for brunch and dinner: Wednesday to Saturday from 4 PM to midnight, and Sunday from 12 PM to 8 PM.

Location

26 Chandler St, Boston, 02116
Explore Boston
Nearby Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
Boston Common
15 minutes' walk
America's oldest public park, featuring serene walking paths and open spaces, ideal for picnics and leisurely strolls.
Boston Public Garden
Boston Public Garden
15 minutes' walk
Famous for its swan boats and beautiful flora, this Victorian garden offers a tranquil escape right in the city center.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
A premier art museum housing an extensive collection from around the world, known for its impressive temporary exhibitions.
New England Aquarium
New England Aquarium
25 minutes' walk
Home to diverse marine life and interactive exhibits, the aquarium also offers whale watching tours in the summer.
Tranquil Yoga Sessions
10 minutes' walk
Local studios offer relaxing yoga classes suitable for all levels, perfect for unwinding after a busy day.
Kayaking on the Charles River
20 minutes' drive
Thrilling kayaking experiences on the Charles River with rental services available. Great for adventure seekers.
The Trophy Room
1 minute' walk
Modern American cuisine in a stylish setting, known for delicious burgers and craft cocktails. Reservations recommended.
Masa
3 minutes' walk
A vibrant space featuring Southwestern flavors and a lively atmosphere, famous for its enchiladas and margaritas.
Wink & Nod
2 minutes' walk
An intimate dining option serving globally inspired dishes with a chic vibe. Perfect for date nights.
House of Blues
15 minutes' drive
A vibrant venue hosting live music and events, with a Southern-inspired menu. Great for a fun night out.
The Wilbur Theatre
15 minutes' drive
Historic theater offering a range of performances from comedy to concerts, making it perfect for an entertaining evening.
How to Navigate the City
  • City Centre
    Boston 20 min  ·  1.0 mi
  • Airports
    Logan (BOS) 13 min  ·  5.3 mi
    Worcester Regional (ORH) 116 min  ·  47.7 mi
  • Train
    Boston South Station 17 min  ·  4600 ft
  • Underground
    Back Bay Metro Station 5 min  ·  1400 ft
  • Bus
    Bus stop 2 min  ·  400 ft
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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 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

Real Guest Reviews & Ratings

What Previous Guests Had to Say
Review summary
Based on recent reviews
Powered by AI
Staypineapple, A Delightful Hotel, South End is celebrated for its distinctive pineapple decor and convenient location, with many finding it easy to walk to Back Bay Station and Boston Common. Guests appreciate the comfy robes and the availability of free refillable water bottles, plus the option to borrow bikes for exploring nearby parks. While some guests have mentioned small rooms, the hotel's overall charm and proximity to restaurants make it a popular choice.
Show moreShow less
Review score
Based on 764 verified reviews
8.6 /10
Great
84 %
Recommend
Location
9.1/10
Staff
9.1/10
Free WiFi
7.7/10
Value for money
8.0/10
Pros
Clean space
Comfy bed
Friendly staff
Cons
Small rooms
Tiny bathroom
Guest reviews
based on 764 reviews
8.6/10
based on 61 reviews
3.5/5
based on 855 reviews
8.5/10
Hannah from Germany
Couple
South End Corner King
3 nights in November 2025
|
Reviewed: January 26, 2026
9/10

surprised by delightfullness

free bikes comfy robes many restaurants
i really liked the free bikes. i rode one to the nearby park. the room had comfy robes. the location had so many restaurants close.
0 Helpful
David from United Kingdom
Couple
South End Corner King
3 nights in November 2025
|
Reviewed: January 22, 2026
5/10
small room lack basic toiletries
the location worked fine for access to local spots.
The room seemed way smaller than expected and really cramped. the air conditioning made constant loud noises. It definitely disrupted sleep. plus, the bathroom lacked basic toiletries. I expect more for what i paid.
0 Helpful
Nathaniel from United States
Couple
Back Bay King
3 nights in November 2025
|
Reviewed: January 06, 2026
9.0/10

Handy hotel for exploring

helpful staff soft robes water bottles lobby bar
Staff was friendly and always willing to help with directions. The hotel has soft robes in the room, something I used. The room included two complimentary bottles of water and a metal bottle. There's a bar in the lobby, it was open late most nights.
Elevators felt old, made noises and moved slowly.
Location
9/10
The hotel is within walking distance of the Boston Common. Subway and bus stops are nearby to the hotel. Streets of Back Bay homes surround the immediate area.
Dining
8/10
The hotel offers a bar with free drinks at check in. Restaurants and diners are near the premises. Cookies in the lobby are free .
Facilities
9/10
Guests can fill water bottles for free at the hotel. Bicycles are available at the hotel. Staff at the front desk offered assistance.
Rooms
10/10
Rooms have pineapple decor on the pillows. The room included soft duvets and pillows. The bathroom was clean and well designed for functionality.
0 Helpful
|
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Questions of the users
About Staypineapple, A Delightful Hotel, South End
Is there a parking facility at the hotel or close by? What are the fees involved?
12 November 2024
There is no parking on-site, but a recommended nearby garage on 100 Clarendon Street charges $36 nightly.
Could you provide the name and location of the nearby parking option?
23 January 2025
The nearby parking facility is called Clarendon Garage.
Is it possible to store my luggage before check-in or after check-out?
10 March 2025
Yes, a secure luggage storage area is available for guests before check-in and after check-out.
Are elevators available in the hotel for easy access to rooms?
15 April 2025
Yes, there is an elevator for guest convenience.
Can you explain what the Naked Experience entails? Is it focused on the linens?
05 May 2024
The Naked Experience promises a cozy, luxurious night with freshly laundered linens and cloud-like European-style duvets, ensuring a restful sleep.
Is there Wi-Fi access throughout the hotel, including guest rooms? Are laundry services available?
22 June 2024
Wi-Fi is available in all areas, including guest rooms. However, the hotel does not offer on-site laundry or dry cleaning services. Nearby services can be arranged.
Are pets allowed at the hotel, and what are the associated fees?
30 July 2024
The hotel is dog-friendly with a nightly pet fee of $25, which includes amenities like a dog bed, treats, and bowls.
What options are available for breakfast nearby since the restaurant on-site is closed?
18 August 2024
The hotel does not serve continental breakfast, but there are several restaurants in the vicinity that offer breakfast.
What is the most convenient way to reach the airport from the hotel?
27 September 2024
Ride-sharing services like Uber and Lyft are the most convenient transportation options for reaching the airport.
Are the bathrooms in the units private?
12 October 2024
Yes, each room is equipped with a private bathroom.
Is there an option for complimentary drinks upon arrival?
29 November 2024
Guests can enjoy a complimentary CORE Welcome Drink upon arrival, with options including house wine, beer, or non-alcoholic beverages.

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