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Staypineapple, A Delightful Hotel, South End
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74 photos
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
Exclusive direct rates
up to 10% less
than on Booking.com
Check rooms and rates
From97US$ /night
Check-in
18Jun2026Select date
Check-out
19Jun2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116
Great
8.5
9.0
/10
4.1
4.2
/5
“The South End is a beautiful area perfect for leisurely strolls.”view full review

Providing guests with bicycle rentals, the 4-star non-smoking Staypineapple, A Delightful Hotel, South End Boston is located approximately a 25-minute walk from the Floating Boston Tea Party Ships & History Museum. Boasting a location within reach of the Trinity Church, the comfortable hotel offers 56 rooms and a lounge bar onsite.

Location

Situated 1.2 km from Boston Common Public Park, this hotel also gives access to such sports venues as the multi-purpose TD Banknorth Garden Arena, which is 2.2 km away. The Museum of Fine Arts is within 30 minutes' walk of the Staypineapple, A Delightful Hotel, South End and Logan airport is 5 km away.

Nature lovers will enjoy the vicinity of Beacon Hill, located a mere 1.8 km away. Standing about 20 minutes' walk away, the historic Unitarian Christian church "King's Chapel" is a hard-to-miss divine tourist destination.

Staypineapple, A Delightful Hotel, South End is just 500 m from Back Bay underground station and fairly close to Arlington city rail.

Rooms

The rooms are equipped with coffee/tea making equipment, along with a flat-screen TV with satellite channels for guests' comfort.

Eat & Drink

Dining options also include Wink & Nod, situated 5 minutes' stroll away.

Leisure & Business

A shared lounge and various recreational opportunities are featured at the Staypineapple, A Delightful Hotel, South End Boston.

View all

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
South End Corner King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Back Bay King
Back Bay King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
room details

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

Amenities designed for comfort – Perfect for layovers & transit travelers
Tasty Eats at Trophy Room
“I had to mention the food at The Trophy Room bar & restaurant! The pineapple teriyaki wings were absolutely delicious and a must-have. It made dining in the hotel a good experience, and paired with their excellent draft beer, it was the perfect way to unwind after a day of exploring.” view full review
Cozy and Clever Design
“My Beautiful King Room was thoughtfully designed with clever storage solutions. I appreciated the large drawer underneath the bed where I could stash my bigger suitcase. It was cozy and efficient, making the most out of the space provided!” view full review
Heavenly Sleep Experience
“The bedding in my room was incredibly comfortable! I loved the European-style duvet, made for a snug and restful night's sleep after a long day. It was exactly what I needed for a good stay!” view full review
Fun Streaming Options
“I was actually surprised to find that I could easily connect my device to stream my favorite shows right on the room's TV. This little feature added a great touch to my downtime in the cozy room - it was like home!” view full review
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

Staypineapple, A Delightful Hotel, South End 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
Landmark
Freedom Trail walk
1.6 mi
Spa Centre
Newbury Street
3900 ft
Church
Trinity Church
2200 ft
Landmark
Boston Children's Museum
1.5 mi
Cemetery
Granary Burying Ground
5100 ft
Monument
Bunker Hill Monument
2.1 mi
Museum
Isabella Stewart Gardner Museum
1.6 mi
Landmark
Beacon Hill
1.2 mi
Monument
New England Holocaust Memorial
1.3 mi
Museum
The Paul Revere House
1.4 mi
Tower
John Hancock Tower
2100 ft
Landmark
Quincy Market
1.3 mi
Museum
USS Constitution Museum
2.0 mi
Museum
The Institute of Contemporary Art
1.5 mi
Public Building
Old State House
1.2 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
Getting around
City Centre
Boston20 min  ·  1.0 mi
Airports
Logan (BOS)13 min  ·  5.3 mi
Worcester Regional (ORH)116 min  ·  47.7 mi
Train
Boston South Station17 min  ·  4600 ft
Underground
Back Bay Metro Station5 min  ·  1400 ft
Bus
Bus stop2 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 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 Wi-Fi
7.6/10
Location
9.2/10
Paid Wi-Fi
7.6/10
Staff
9.2/10
Value for money
8.1/10
Guest reviews
based on 61 reviews
3.5/5
based on 875 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.
Open reviews

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Check-in
18Jun2026Select date
Check-out
19Jun2026Select date
Rooms and Guests2 Guests, 1 Room
  • Overview
  • Rooms
  • Price calendar
  • Facilities
  • Location
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