Welcome to Staypineapple, A Delightful Hotel, South End – Boston

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From97US$ /night
Check-in
26Oct2025Select date
Check-out
27Oct2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

Staypineapple, A Delightful Hotel, South End is a 4-star award-winning hotel in the charming South End neighborhood with genuine vintage fittings such as the original black painted iron staircase that snakes its way up the building. This modern hotel sits just steps away from many of Boston's famous historical sites, stylish stores, and great restaurants.

Luxurious Comfort Beds

Each thoughtfully designed room at Staypineapple features plush pillow top beds topped with European style double duvets and upscale amenities. The Naked Experience translates as two fluffy duvets, thus avoiding any tug of war, atop soft white linens and a cushiony mattress topper for exceptional comfort.

Impressive Dining Options

The Trophy Room is a long room lined with windows overlooking the street where both food and drink menus are ready to impress with tasty versions of favorites. The adjacent Berkeley Perk Café serves cooked items such as breakfast tacos and omelettes, while guests can perk up with a cup of coffee and signature pineapple treats in the lobby.

Bikes and Markets

Help-yourself coffee is available in the lobby, where bright yellow bikes stand ready for guests' use to explore the city. There are several local attractions including the summer-to-December SoWa Open Market, which has artist and vintage wares, and SoWa First Fridays, an art market held on the first Friday of every month.

Strategic City Position

The central location of Staypineapple, A Delightful Hotel, South End on the border of Back Bay and South End means you're just a short walk or cab ride away from a memorable dinner or Red Sox game. The hotel is only 400 m from Back Bay, 550 m from Arlington, and 3 km from Beacon Street.

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Select your room type

Choose from doubles, suites, or family rooms, many with breakfast, flexible cancellation, and promotional rates
South End Corner King
2 persons
18 m² 
1 King-size bed
Shower
Coffee machine
Back Bay King
2 persons
18 m² 
1 King-size bed
Shower
Coffee machine

Price and Room Availability Calendar

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Getting around

A guide to all available transportation options

City Centre
Boston 1.6 km
Airports
Logan (BOS) 8.6 km
Worcester Regional (ORH) 76.7 km
Train
Boston South Station 1.4 km
Underground
Back Bay400 m
Bus
Bus stop100 m

Facilities

Boutique hotels design their amenities with your relaxation and unique travel experiences in mind

General

  • No smoking on site
  • Free 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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Location

26 Chandler St, Boston, Massachusetts, United States, 02116
Map view
26 Chandler St, Boston, Massachusetts, United States, 02116
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
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Check-in
26Oct2025Select date
Check-out
27Oct2025Select date
Rooms and Guests2 Guests, 1 Room