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 – A Favorite for Families in Boston

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Check rooms and rates
From$97 /night
Check-in
21Sept
Check-out
22Sept
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

Boutique hotel in Boston's South End with complimentary bikes and a pet-friendly policy

Rooms & Amenities

Staypineapple, A Delightful Hotel, South End offers the Naked Experience bedding, a system of individual European-style duvets that prevent cover-hogging. All 56 rooms include a flat-screen TV with Chromecast streaming capability and a walk-in marble shower. A daily Amenity Fee covers high-speed Wi-Fi, use of the reusable water bottle at the Water Bar, and afternoon treats served in the lobby.

Dining & Entertainment

The on-site Trophy Room restaurant serves an all-American menu and operates as a lively neighborhood bar. Guests receive two complimentary drink coupons at check-in, redeemable for beer or wine at Trophy Room. The hotel also offers Daily Afternoon Delights, which include signature pineapple treats and fresh coffee in the lobby.

Location & Transportation

The hotel sits on the border of Back Bay and South End, within a 10-minute walk of Back Bay station and the shops of Newbury Street. Fenway Park is a 20-minute walk away, and the Boston Center for the Arts is three blocks from the front door. Complimentary bicycles are available for guests who want to explore the city on two wheels.

Pet-Friendly Policies

The hotel welcomes dogs with specialized amenities, including pet baskets, pet bowls, and a community partnership with a local dog rescue organization. The general manager's Bernedoodle, Goofy, is a regular presence in the lobby, greeting guests. There is no weight limit or breed restriction for dogs, and no additional deposit required beyond the standard Amenity Fee.

Business & Practical Details

Concierge service and luggage storage are available through the 24-hour front desk, which also provides invoice processing for business travelers. The hotel is a 15-minute walk from the Hynes Convention Center and a 5-minute walk from the Orange Line at Back Bay. The daily Amenity Fee consolidates parking coordination via SpotHero, food and drink credits, and all room-based technology into one flat charge.

Highlights

Bedding: Naked Experience with individual European duvets

Dining: Trophy Room all-American menu with complimentary drink coupons

Service: Daily Afternoon Delights with pineapple treats & coffee

Pet Policy: No weight limit, no breed restriction, free pet amenities

Location: Steps from Back Bay station, Fenway Park, Newbury Street

Transport: Complimentary bicycles for city exploration

Value: Daily Amenity Fee covers Wi-Fi, water bottle, drinks, and parking help

“What stands out is the seamless experience, from attentive staff to thoughtful extras like free-flowing coffee and chilled water. The pineapple theme is carried through with charming details and especially comfortable beds. Its Back Bay location offers a relaxed vibe with easy access to Boston, best explored using the hotel's bikes.”
Hotel logo
Grace WhitmanContent & Editorial Director at Familyhotels

Choose from a variety of room types

Choose from a wide variety of rooms designed for families, including double rooms, family suites, and rooms with breakfast included
Back Bay King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower
South End Corner King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower

Availability and pricing for your selected dates

Book your family’s getaway in a snap with up-to-date availability and pricing!
September 2026 - September 2027
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Check-in/ Check-out

Facilities

Each family-friendly hotel provides top-notch amenities for an unforgettable stay with your loved ones
Facilities: Great
8.3/10Review score

General

  • No smoking on site
  • Wi-Fi
  • 24-hour reception
  • Pets allowed
  • Luggage storage
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access

Guest Parking

  • No parking available.

Services

  • Pet amenities available

Dining

  • Restaurant
  • Bar/ Lounge area

Room features

  • Air conditioning
  • Heating
  • Tea and coffee facilities

Media

  • Flat-screen TV
Show more

Dining Onsite

At Staypineapple, A Delightful Hotel, South End, culinary experiences come alive with vibrant flavors in a modern setting. Guests can indulge in American dishes at the stylish Trophy Room, perfect for a cozy brunch or an alluring dinner.
  • Trophy Room

    American
    Ambiance
    A modern restaurant that exudes a warm and inviting atmosphere, making it the perfect spot to relax and enjoy a meal.
    Key Offerings
    A highlight is the avocado toast topped with braised tomatoes and goat cheese, alongside a selection of carefully crafted dishes that reflect local culinary traditions.
    Reservation
    Reservations recommended.
    Open for dinner Wednesday through Sunday, with brunch available on Sundays.

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, 02116
Explore Boston
Explore the South End
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
15 minutes' walk
Historic park offering scenic walkways, open spaces, and a playground. Great for picnics or a leisurely stroll.
Boston Public Garden
15 minutes' walk
Beautifully landscaped gardens featuring swan boats and vibrant flower displays. A popular spot for photos and relaxing.
Museum of Fine Arts
25 minutes' walk
Renowned art museum showcasing a vast collection from ancient to contemporary art. Offers guided tours and events.
Faneuil Hall Marketplace
25 minutes' walk
A historic marketplace with shops, eateries, and entertainment. Known for its vibrant atmosphere and street performers.
Bike Rentals along the Charles River
10 minutes' walk
Bike along scenic paths with views of the river and skyline. Rentals available nearby; perfect for all skill levels.
Yoga in the Park
10 minutes' walk
Outdoor yoga classes at Boston Common. Ideal for relaxation and mindfulness; check schedules for availability.
Harbor Cruises
10 minutes' drive
Cruises offering stunning views of Boston's harbor and skyline. Great for sightseeing; tickets can be booked online.
The Trophy Room
1 minute' walk
A cozy bar with American fare and a vibrant atmosphere. Known for burgers and unique cocktails; casual and inviting.
Masa
3 minutes' walk
A lively spot offering Southwestern cuisine with a flair. Popular for its brunch and extensive tequila selection.
Bootleg Special
3 minutes' walk
A stylish bar and restaurant featuring craft cocktails and modern cuisine. Great ambiance; reservations recommended.
House of Blues
10 minutes' drive
Live music venue offering diverse performances across genres. Fun atmosphere, renowned for its Southern-inspired menu.
Laugh Boston
10 minutes' drive
Comedy club featuring local and national acts. Ideal for a night of laughs, suitable for adults and older teens.
Tips on navigating the city
  • 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
Get access to exclusive early booking discounts for your family’s upcoming getaway
Book now and enjoy exclusive rates on your family vacation!
Check Rates
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

Family-focused reviews and ratings

Read feedback from other families who have stayed to ensure you make the right choice.
Review score
Based on 1015 verified reviews
8.7 /10
Great
86 %
Recommend
Breakfast
8.3/10
Cleanliness
8.9/10
Comfort
8.8/10
Facilities
8.3/10
Free Wi-Fi
7.7/10
Location
9.1/10
Paid Wi-Fi
8.6/10
Staff
9.1/10
Value for money
8.0/10
Pros
Helpful staff
Clean rooms
Walkable location
Darling decor
Cozy place
Cons
Extra charges
Small room
Guest reviews
based on 61 reviews
3.5/5
based on 831 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 at 16:00 and check-out is at 12:00.
How far is Staypineapple, A Delightful Hotel, South End from Fenway Park?
The hotel is approximately 2 km from Fenway Park.
What dining options are available at Staypineapple, A Delightful Hotel, South End?
The on-site restaurant, Trophy Room, offers an all-American menu.
What are some nearby restaurants to Staypineapple, A Delightful Hotel, South End?
Nearby dining options include Berkeley Perk Café (0.5 km), Masa (0.5 km), and Grill 23 & Bar (0.5 km).
What room amenities can guests expect at Staypineapple, A Delightful Hotel, South End?
Rooms include air conditioning, a flat-screen TV, high-speed Wi-Fi, and designer bath products.
Is there a bar available at Staypineapple, A Delightful Hotel, South End?
Yes, the bar is open until 2:00 AM every night.
What facilities for business travelers are available at Staypineapple, A Delightful Hotel, South End?
The hotel provides a work desk and 24-hour front desk access for business needs.
How far is Staypineapple, A Delightful Hotel, South End from Boston South station?
The hotel is 2 km from Boston South station.
What recreational activities can guests enjoy at Staypineapple, A Delightful Hotel, South End?
Guests can take advantage of complimentary bicycle rentals for exploring the city.
Does Staypineapple, A Delightful Hotel, South End provide any food and beverage services throughout the day?
Yes, guests can enjoy daily Afternoon Delights featuring signature pineapple treats and coffee.

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