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

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Check rooms and rates
From$97 /night
Check-in
10Jun
Check-out
11Jun
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, 02116
-
Close to Copley Square
Great
8.5
9.0
/10
4.1
4.3
/5

3-star boutique hotel in Boston's South End

Location

Staypineapple Boston is situated in the South End, one of Boston's most sought-after neighborhoods. Steps away from Back Bay, the hotel offers easy access to famous historical sites, stylish stores, and renowned restaurants. A quick 10-minute walk to Arlington Station provides direct train access to key attractions such as Fenway Park.

Rooms

The hotel offers thoughtfully designed rooms featuring plush pillow top beds with European-style double duvets. High-definition TVs allow guests to stream favorite shows or movies. Each room is equipped with upscale amenities, including a walk-in shower and a reusable water bottle pre-filled with purified water.

Dining

Trophy Room serves all-American cuisine and offers a lively atmosphere. Guests can enjoy breakfast, casual lunches, and dinner featuring local favorites. The hotel also provides Afternoon Delights with coffee and pineapple treats in the lobby from 3:30pm to 6:30pm daily.

Amenities

Staypineapple Boston boasts unique amenities like The Naked Experience, featuring cloud-like duvets and cozy robes. The Water Bar in the lobby allows guests to refill bottles with cold, hot, still, or sparkling water. Additionally, guests can use stylish bikes to explore the city or relax in the lobby with signature snacks and beverages.

Pet-Friendly Policies

The hotel welcomes pets with its Pineapple Pup Package, including a dog bed and treats. Special amenities for pets make it convenient for travelers with furry companions. Off-leash areas at nearby parks like Peters Park and Boston Common offer space for dogs to roam.

Highlights

Location: steps away from Back Bay

Dining: Trophy Room with all-American favorites

Amenities: The Naked Experience with cloud-like duvets

Pet-Friendly: Pineapple Pup Package available

“The attention to detail here is truly notable, from the quirky, colorful decor to the thoughtfully included amenities like reusable water bottles and in-room Keurig machines. Staff members consistently proved themselves helpful and friendly, making for a welcoming and comfortable stay in a well-situated neighborhood. It's a place I'd easily return to.”
Hotel logo
James DavidEditor-in-Chief at Usmassachusetts

Select your room type

Staypineapple, A Delightful Hotel, South End offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
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

Price and Room Availability Calendar

Check availability and prices for your dates now!
June 2026 - June 2027
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Check-in/ Check-out

Facilities

Staypineapple, A Delightful Hotel, South End offers amenities for your comfortable stay and unforgettable experiences
Facilities: Great
8.4/10Review 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

Experience delightful dining at Staypineapple, A Delightful Hotel, South End, where modern American cuisine meets the vibrant charm of the South End neighborhood. Each culinary offering promises a comforting escape, perfect for travelers seeking authentic flavors and memorable moments.
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 fresh, contemporary design that enhances the dining experience.
Key Offerings
Indulge in standout dishes like avocado toast topped with braised tomatoes and goat cheese, crafted to celebrate local flavors.
Reservation
Recommended.
Open for brunch and dinner.

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, 02116
Explore Boston
Explore Boston's Vibrant Scene
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
15 minutes' walk
A historic park featuring lush landscapes and paths, perfect for leisurely strolls and picnics in the heart of Boston.
Faneuil Hall Marketplace
25 minutes' walk
A bustling marketplace with shops, food vendors, and street performers that brings the city's spirit alive year-round.
Museum of Fine Arts
25 minutes' walk
Offers an impressive collection of art from around the world, including free admission days and educational programs.
George Washington Statue
5 minutes' walk
A prominent landmark showcasing a statue of America's founding father, surrounded by historic architecture.
Boston Freedom Trail Walk
30 minutes' walk
A guided tour along the historic Freedom Trail, ideal for history enthusiasts exploring Boston's revolutionary past.
Yoga at the Park
15 minutes' walk
Relax and rejuvenate with outdoor yoga classes in Boston Common, available during the warmer months.
Biking the Esplanade
10 minutes' ride
Bike along the scenic Charles River Esplanade with rental services available nearby, perfect for adventure seekers.
The Trophy Room
1 minute' walk
A casual eatery known for its comfort food and vibrant atmosphere, featuring burgers and craft cocktails.
Masa
3 minutes' walk
Offers a unique blend of Southwestern cuisine in a lively setting with outdoor seating and signature margaritas.
Cosmica
2 minutes' walk
A trendy restaurant serving innovative Latin dishes, perfect for a casual meal or a romantic dinner.
House of Blues
15 minutes' walk
Live music venue featuring genres from blues to rock, with a vibrant atmosphere and diverse events.
Laugh Boston
5 minutes' ride
A comedy club showcasing local and national stand-up acts, perfect for a fun night out with friends.
Citi Performing Arts Center
15 minutes' walk
Hosts Broadway shows and concerts in a historic venue, appealing to theater lovers and families alike.
Getting around
  • 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

Reviews and Ratings

Feedback about Staypineapple, A Delightful Hotel, South End from previous guests about their experience.
Review score
Based on 917 verified reviews
8.7 /10
Great
85 %
Recommend
Breakfast
7.5/10
Cleanliness
8.9/10
Comfort
8.8/10
Facilities
8.4/10
Free WiFi
7.6/10
Location
9.2/10
Paid Wi-Fi
7.6/10
Staff
9.2/10
Value for money
8.1/10
Pros
Pineapple decor
Complimentary water bottle
Helpful front desk staff
Cons
Small rooms
Noisy environment
Bicycle maintenance issues
Guest reviews
based on 61 reviews
3.5/5
based on 879 reviews
8.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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