Staypineapple, A Delightful Hotel, South End, Boston | Explore Room Options, Reviews & Pricing for 2025

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Key details

About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116

“The location was fantastic for exploring all of Boston!”view full review

Staypineapple, A Delightful Hotel, South End stands as a 4-star award-winning property in Downtown Boston's charming South End district, featuring The Naked Experience with European-style individual duvets and designer bath products.

Luxurious Double Duvet Comfort

Rooms at Staypineapple showcase plush pillow-top beds with European-style double duvets and crystal lamps with charging points. The South End Corner King rooms offer added tranquility with enhanced city views.

Street-View Dining Experience

Trophy Room, a street-view venue with window-lined walls, serves American classics and creative cocktails including the signature Trophy Wife with passion fruit and elderflower vodka. Berkeley Perk Café offers breakfast tacos and omelets.

Modern Guest Amenities

The lobby features complimentary afternoon coffee service and yellow bikes for guest use. Streaming-capable HDTVs and unlimited high-speed Wi-Fi enable entertainment options.

Prime Downtown Location

Located steps from Back Bay, Staypineapple Boston provides direct access to Freedom Trail sites, the SoWa Open Market, and local art venues. Arlington Station sits within a 10-minute walk, offering connections to Fenway Park.

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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals

South End Corner King

Max:

2 persons

195 sq. feet

Bed options:

1 King-size bed

Shower

Coffee machine

room details

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Back Bay King

Max:

2 persons

195 sq. feet

Bed options:

1 King-size bed

Shower

Coffee machine

room details

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Price and Room Availability Calendar

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Getting around

Available transportation options

City Centre

Boston 1.0 mi

Airports

Logan (BOS) 5.3 mi

Worcester Regional (ORH) 47.7 mi

Train

Boston South Station4600 ft

Underground

Back Bay1400 ft

Bus

Bus stop400 ft

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

Delicious Dining Experience

“During my stay, I had the pleasure of dining at The Trophy Room. I ordered the clam chowder, and it was absolutely divine! It's a must-try-you'll find yourself wanting more. The atmosphere was vibrant and lively, making my meal even better.” view full review

Comfy and Charming Room

“The bedroom in my Beautiful King Room was quirky and good, with pineapple-themed decor that added a fun touch. The bed was incredibly comfortable, ensuring I had restful nights after a long day of exploring. I loved the fluffy robes and the little dog stuffed animal named Dash the pineapple pup, which I had the option to 'adopt'!” view full review

Unique and Thoughtful Amenities

“My room featured a clever use of space, with plenty of hiding spots for my luggage and hooks for hanging clothes instead of a cumbersome closet. Although the room and bathroom were on the smaller side, the design maximized functionality, making it cozy and efficient for my stay.” view full review

Cute and Functional Bathroom

“The bathroom, while compact, featured very hot water, which I appreciated after long hours out in the chill of Boston. The clever layout made good use of the space, though I did notice the squeeze between the shower door and sink could be tight for some. Overall, it served its purpose well!” view full review

General

No smoking on site
Wi-Fi
No parking
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

Location

26 Chandler St, Boston, Massachusetts, United States, 02116

Map view

26 Chandler St, Boston, Massachusetts, United States, 02116

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

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