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From97US$ /night
Check-in
15Mar2026Select date
Check-out
16Mar2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel overview and key features

26 Chandler St, Boston, Massachusetts, United States, 02116
-
Close to the Freedom Trail
Great
8.5
9.0
/10
4.2
4.2
/5

Staypineapple, A Delightful Hotel, South End is a 4-star hotel located 1.9 miles from Logan International Airport, with easy access via MA-1A South and MA-3 N. The property sits on the border of Back Bay and South End, 1805 ft from Arlington Station and 1312 ft from Back Bay. Nearby attractions include Trinity Church (0.3 miles), Copley Square (0.3 miles), and Fenway Park (1.2 miles).

Comfortable & Stylish Rooms

Each room at Staypineapple Boston features plush pillow-top beds with European-style double duvets, high-speed Wi-Fi, and designer bath products. The Naked Experience includes cloud-like individual duvets, cozy robes, and large towels. Select rooms, such as the South End Corner King, offer added quiet and city views.

On-Site Dining Options

The Trophy Room serves American cuisine with brunch, dinner, and late-night cocktails, including the signature Trophy Wife vodka drink. The adjacent Berkeley Perk Café offers breakfast tacos and omelets. Both venues feature locally sourced ingredients and craft beverages.

Local Attractions & Activities

Guests can explore the SoWa Open Market for vintage wares or attend SoWa First Fridays art events. The hotel provides yellow beach cruisers for city rides. The bar stays open until 2am, offering a lively spot for cocktails and trivia nights.

Convenient Guest Services

Staypineapple, A Delightful Hotel offers high-speed Wi-Fi, streaming-capable HDTVs, and reusable PATH water bottles. The lobby includes a Water Bar for refills and a Quick Bites & Bevvies cooler. Group services are available for customized event planning.

“What stands out here is the South End location, near Back Bay but with its own distinct vibe. It's a boutique experience, to be sure, with fun pineapple accents and the brand's signature bedding. Plus, the pet-friendly policy and on-site Trophy Room add genuine appeal.”
Hotel logo
Amelia BrooksLead Hotel Editor at Hotelairport
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Choose your ideal room style

Choose from family rooms, suites, flexible cancellation & more
South End Corner King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine
Back Bay King
2 persons
195 sq. feet 
1 King-size bed
Shower
Coffee machine

Prices and Availability

Check availability and prices for your travel dates right now!

Facilities

Stay relaxed and refreshed just minutes from the airport
Facilities: Great
8.2/10Review 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 Staypineapple, A Delightful Hotel, South End, guests can indulge in tantalizing American cuisine amidst a modern and inviting setting. From brunch delights to intimate dinners, the dining options promise a flavorful experience that reflects the charm of the vibrant South End neighborhood.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American
Ambiance
Modern and lively, with a welcoming atmosphere perfect for unwinding after a day of exploration.
Key Offerings
Delight in seasonal offerings like creamy avocado toast topped with braised tomatoes and goat cheese, ideal for brunch, or savor a cozy dinner accompanied by curated craft cocktails.
Reservation
Reservations recommended to ensure a pleasant dining experience.
Wednesday to Saturday from 4:00 PM to Midnight, Sunday from 12:00 PM to 8:00 PM.

Location info

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
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
Explore Boston
Explore South End Attractions
Top Attractions
Activities
Dining
Entertainment
Boston Public Garden
Boston Public Garden
15 minutes' walk
Public park known for its beautiful swan boats and vibrant flower beds. Ideal for leisurely strolls and photography.
Fenway Park
Fenway Park
25 minutes' walk
Historic baseball stadium, home of the Boston Red Sox. Offers guided tours showcasing its iconic memorabilia.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
Lively marketplace with a variety of eateries and shops. Features street performances and events throughout the year.
Boston Common
Boston Common
15 minutes' walk
America's oldest public park, perfect for picnics and relaxation. Hosts seasonal events like free movie nights.
Bike Rentals Along the Charles River
15 minutes' walk
Biking along the scenic Charles River esplanade offers stunning views of the city. Rentals available nearby.
Spa at the Mandarin Oriental
10 minutes' walk
Luxurious spa experience with a variety of treatments. Ideal for relaxation after a busy day exploring Boston.
Yoga Classes at Back Bay
8 minutes' walk
Daily yoga classes for all levels in a serene atmosphere. Perfect for recharging during your stay.
Boston Duck Tours
15 minutes' walk
Unique land and water tour of Boston in an amphibious vehicle. Family-friendly and fun for all ages.
The Trophy Room
The Trophy Room
1 minute' walk
Casual spot known for gourmet burgers and craft cocktails. Vibrant atmosphere ideal for groups.
Wink & Nod
Wink & Nod
2 minutes' walk
Innovative cocktail bar with a seasonal small plates menu. Reservations recommended for peak hours.
Masa
Masa
3 minutes' walk
Mexican cuisine hotspot famous for its tapas and margaritas. Bright decor creates a lively dining experience.
Bootleg Special
Bootleg Special
3 minutes' walk
Southern-inspired eatery with a fun, relaxed vibe. Great for brunch and diverse dietary options available.
The Wilbur Theatre
20 minutes' walk
Historic theater showcasing live performances and comedy shows. Check schedule for family-friendly events.
House of Blues
25 minutes' walk
Live music venue featuring performances from various artists. Offers a vibrant atmosphere and great food.
Laugh Boston
20 minutes' walk
Comedy club presenting local and national acts. Enjoy a fun night out with friends or family in a cozy environment.
Lansdowne Street Nightlife
25 minutes' walk
Popular nightlife district with bars and clubs. Great for those looking to experience Boston's vibrant nightlife scene.
Getting around
City Centre
Boston20 min  ·  1.0 mi
Airports
Logan International Airport (BOS)13 min  ·  5.3 mi
Worcester Regional Airport (ORH)116 min  ·  47.7 mi
Train
Boston South Station17 min  ·  4600 ft
Underground
Back Bay5 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

Guest scores and detailed hotel feedback

Past guest experiences and opinions
Review score
Based on 641 verified reviews
8.6/10
Great
86%
Recommend
Breakfast
7.5/10
Cleanliness
8.7/10
Comfort
8.7/10
Facilities
8.2/10
Free Wi-Fi
8.1/10
Location
8.9/10
Paid Wi-Fi
7.5/10
Staff
9.0/10
Value for money
7.9/10
Pros
Cute theme
Friendly staff
Good location
Clean rooms
Cons
Shabby entrance
Extra charges
Uncomfortable bed
Guest reviews
based on 61 reviews
3.5/5
based on 930 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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FAQs
About Staypineapple, A Delightful Hotel, South End
What nearby attractions are within walking distance from Staypineapple, A Delightful Hotel, South End?
Nearby attractions include Fenway Park (1 km), Boston Center for the Arts (1 km), and the scenic Back Bay area (1 km).
What is the distance from Staypineapple, A Delightful Hotel, South End to Faneuil Hall Marketplace?
The hotel is approximately 2 km from Faneuil Hall Marketplace.
What amenities are offered at Staypineapple, A Delightful Hotel, South End?
Amenities include free Wi-Fi, luggage storage, 24-hour reception, bar/lounge area, and an on-site restaurant.
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.
Is there on-site dining available at Staypineapple, A Delightful Hotel, South End?
The hotel features an on-site restaurant, Trophy Room, which offers an all-American menu.
Are there any popular restaurants near Staypineapple, A Delightful Hotel, South End?
Nearby restaurants include Masa (0.5 km), The Friendly Toast (0.5 km), and Grill 23 & Bar (0.5 km).
What type of rooms are available at Staypineapple, A Delightful Hotel, South End?
Rooms feature air conditioning, free Wi-Fi, flat-screen TVs, plush pillow-top beds, and designer bath products.
Is there a fitness or wellness facility at Staypineapple, A Delightful Hotel, South End?
The hotel offers complimentary bike rentals for guests to explore the city.
Are there any historical sites nearby Staypineapple, A Delightful Hotel, South End?
The hotel is within walking distance to historic sites along the Freedom Trail, including the Old State House (2 km).
What services does Staypineapple, A Delightful Hotel, South End provide for business travelers?
The hotel features a work desk in each room and 24-hour front desk access.
What languages are spoken by the staff at Staypineapple, A Delightful Hotel, South End?
The staff is primarily English-speaking.
Does Staypineapple, A Delightful Hotel, South End offer any special experiences for guests?
The hotel features an exclusive Naked Experience with individual duvets for enhanced comfort.

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Rooms and Guests2 Guests, 1 Room