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 - Your Boutique Escape in Boston

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Check rooms and rates
From$97 /night
Check-in
27May
Check-out
28May
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
4.2
4.3
/5

Amenities

A daily Amenity Fee covers high-speed Wi-Fi, in-room Keurig coffee, a reusable water bottle with access to the Water Bar, and two drink coupons for the Trophy Room bar. Complimentary bicycle rental allows guests to explore the South End and Back Bay neighborhoods at their own pace. Each afternoon, the hotel serves Daily Afternoon Delights with signature pineapple treats and coffee in the lobby.

Rooms

Every guest room features the Naked Experience - two European-style individual duvets that eliminate blanket-sharing issues. Rooms include a 43-inch flat-screen TV with streaming capability, an iPod docking station, and a private bathroom with a walk-in marble shower. A work desk and 24-hour front desk access are provided for convenience.

Location

The hotel sits on the border of Back Bay and South End, steps from the shops and restaurants of Newbury Street. Fenway Park is a 15-minute walk, and Back Bay Station is a 5-minute walk for subway and commuter rail access. The Boston Center for the Arts and the historic brownstone district are within a 10-minute stroll.

Dining

The on-site Trophy Room serves an all-American menu for breakfast, lunch, and dinner in a lively bar setting. Two complimentary drink coupons are included with the daily Amenity Fee and can be redeemed at the Trophy Room bar. Afternoon cookies and coffee are available daily in the lobby as part of the hotel's Daily Afternoon Delights.

Pet-Friendly

Staypineapple welcomes dogs with specialized pet amenities, including a pet basket and pet bowls in the room. There are no weight or breed restrictions, and the hotel provides pet-friendly recommendations for nearby parks and walking routes. The property is entirely non-smoking, including all guest rooms and common areas.

Highlights

Amenities: Daily Amenity Fee covers Wi-Fi, coffee, water bottle, and two bar drinks

Rooms: Naked Experience European-style duvets and walk-in marble shower

Location: 5-minute walk to Back Bay Station, 15 minutes to Fenway Park

Dining: Trophy Room all-American restaurant and bar

Pet-Friendly: No weight or breed restrictions, pet basket and bowls included

Transport: Complimentary bicycle rental for city exploration

“I found the hotel's charming, pineapple-themed decor quite delightful, creating a cozy atmosphere that made staying in a welcome option. Its South End location proves exceptionally convenient for exploring Boston on foot or utilizing the nearby public transport, though a heads-up for those needing a fridge or microwave is prudent. The exceptionally comfortable bedding and friendly staff, however, left a lasting impression of a truly welcoming stay.”
Hotel logo
James DavidEditor-in-Chief at Wonderfulhotels

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!
May 2026 - May 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
8.5/10Review 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 Trophy Room, indulge in contemporary American dining in a modern setting designed to celebrate relaxation and conversation. Whether it's brunch or dinner, guests can revel in thoughtfully prepared dishes that highlight seasonal ingredients and local flavors, all while soaking in the vibrant ambiance of the South End.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American
Ambiance
Modern, inviting setting perfect for casual gatherings and intimate dinners.
Key Offerings
Signature dishes feature delights such as avocado toast topped with braised tomatoes and goat cheese, making it a beloved spot for both brunch and dinner. A selection of local wines and craft cocktails complement the menu, enhancing the overall experience.
Reservation
Recommended for dinner.
Open for brunch and dinner; hours vary.

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, 02116
Explore Boston
Explore Boston's South End
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
15 minutes' walk
America's oldest public park, offering scenic landscapes and vibrant events year-round.
Boston Public Garden
15 minutes' walk
Famous for its swan boats and picturesque botanical gardens, ideal for a leisurely stroll or picnic.
Museum of Fine Arts
25 minutes' walk
A vast collection of art from around the world, featuring special exhibits and free admission days.
Fenway Park
25 minutes' walk
Home of the Boston Red Sox, this iconic ballpark offers tours and a vibrant atmosphere during game days.
Discover the local attractions near Staypineapple, A Delightful Hotel, South End
Explore notable landmarks near Staypineapple A Delightful Hotel South End Boston to enhance your visit in the South End neighborhood.
Great for casual sightseeing with beautiful architecture: Copley Square
Ideal for book lovers and architecture enthusiasts: Boston Public Library
Perfect for panoramic views of the Boston skyline: Skywalk Observatory
Well suited for history buffs and walking tours: Freedom Trail
Best for baseball fans and sports events: Fenway Park
Ideal for art lovers and cultural experiences: Museum of Fine Arts
Suited for those interested in historical sites: Granary Burying Ground
Boston Freedom Trail Walk
30 minutes' walk
Self-guided tours along this historic path lead to 16 significant sites reflecting America's revolutionary history.
Yoga at Boston Public Garden
15 minutes' walk
Relaxing outdoor yoga sessions in serene surroundings. Check local listings for class schedules.
Bike Rentals along the Charles River
10 minutes' drive
Thrill-seekers can rent bikes to explore the scenic paths along the river. Rentals available nearby.
Tranquil Spa Retreats
10 minutes' drive
Nearby wellness centers offer massages and rejuvenating treatments, perfect for relaxation after your day.
The Trophy Room
1 minute' walk
An upscale spot known for its classic American dishes and vibrant ambiance, perfect for casual dining.
Masa
3 minutes' walk
Latin-inspired fare with a lively atmosphere; renowned for its innovative cocktails and tasty tapas.
Cosmica
2 minutes' walk
An eclectic menu featuring fresh ingredients, with a cozy ambiance for a delightful dining experience.
Wink & Nod
2 minutes' walk
A hidden gem with a unique cocktail menu and seasonal dishes, reservations recommended for a cozy ambiance.
Discover dining options near Staypineapple, A Delightful Hotel, South End
Enjoy the diverse dining options near Staypineapple A Delightful Hotel South End Boston that cater to a variety of tastes.
Great for casual dining with Mexican cuisine: Masa
Perfect for steak lovers and upscale dining: Grill 23 & Bar
Well suited for breakfast and brunch lovers: The Friendly Toast
Ideal for enjoying creative cocktails and shared plates: Cosmica
Best for unique dining experiences with a seasonal menu: Wink & Nod
Suited for quick sweets and coffee: Blackbird Doughnuts
Works well for casual American fare: Delux Cafe
Perfect for a relaxed coffee break: Berkeley Perk Cafe
The Wilbur Theatre
10 minutes' drive
A historic venue featuring a variety of performances including comedy, music, and live shows for all ages.
Caboose Productions
2 minutes' walk
Offers fun improv and sketch comedy shows, popular among locals. Check their schedule for performances.
The Lansdowne Pub
15 minutes' walk
A lively Irish pub known for its live music and vibrant atmosphere, perfect for a night out with friends.
The House of Blues
15 minutes' drive
Iconic venue for music lovers, hosting live performances spanning various genres and a fun bar scene.
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 923 verified reviews
8.7 /10
Great
85 %
Recommend
Breakfast
7.5/10
Cleanliness
8.9/10
Comfort
8.9/10
Facilities
8.5/10
Free WiFi
7.2/10
Location
9.2/10
Paid Wi-Fi
7.6/10
Staff
9.2/10
Value for money
8.2/10
Pros
Comfortable beds
Accessible location
Friendly staff
Cons
Small rooms
Noise issues
Limited storage
Guest reviews
based on 61 reviews
3.5/5
based on 885 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
FAQs
About Staypineapple, A Delightful Hotel, South End
What are the check-in and check-out times at Staypineapple, A Delightful Hotel, South End?
Check-in is from 16:00 and check-out is by 12:00.
How far is Staypineapple, A Delightful Hotel, South End from the nearest airport?
The hotel is approximately 10 km from Logan International Airport.
What dining options are available at Staypineapple, A Delightful Hotel, South End?
Dining options include the Trophy Room, an on-site restaurant serving an all-American menu.
What room amenities can guests expect at Staypineapple, A Delightful Hotel, South End?
Rooms feature high-speed Wi-Fi, flat-screen TVs, air conditioning, and coffee makers.
What popular attractions are near Staypineapple, A Delightful Hotel, South End?
Nearby attractions include Fenway Park (1 km), the Museum of Fine Arts (1 km), and the Freedom Trail (2 km).
What are the nearby dining options to Staypineapple, A Delightful Hotel, South End?
Nearby restaurants include Grill 23 & Bar (0 km), Berkeley Perk Café (0.5 km), and The Friendly Toast (0.5 km).
Does Staypineapple, A Delightful Hotel, South End offer business services?
The hotel provides 24-hour front desk access and a work desk in each room for guest convenience.
What unique features does Staypineapple, A Delightful Hotel, South End have?
The hotel offers a unique Naked Experience with European-style individual duvets and a fun pineapple-themed decor.
Is there a bar available at Staypineapple, A Delightful Hotel, South End?
Yes, the hotel features a bar/lounge area that is open until 2:00 am.
What recreational activities are available at Staypineapple, A Delightful Hotel, South End?
Guests can rent bicycles at the hotel to explore the city.

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