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18Jan2026Select date
Check-out
19Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116
-
Close to Copley Square
Great
8.4
9.0
/10
4.1
4.3
/5

Rooms: Naked Experience

Staypineapple Boston, A Delightful Hotel, provides a modern hotel experience in one of our country's most historic cities. Every room at Staypineapple, South End, features a flat-screen TV and iPod docking station. Each of the thoughtfully designed rooms feature plush pillow top beds topped with European style double duvets. Rooms include high-speed Wi-Fi, designer bath products, a work desk, and a telephone with access to the 24-hour front desk for guest convenience. The hotel provides your choice of coffee or tea for use with the in-room Keurig. Rooms feature yellow bedside shelf tables, over which hang shimmering crystal lamps with charging points. The Staypineapple's signature Naked Experience translates as two fluffy duvets atop soft white linens and a cushiony mattress topper. Guests can also take advantage of perks like the CORE Welcome Drink. The South End Corner King provides added quiet and peace of mind.

Trophy Room Dining

The Trophy Room features a menu of familiar favorites. Both the food and drink menus include tasty choices, like avocado toast with braised tomatoes and goat cheese. The Trophy Room is a long room lined with windows overlooking the street. The bar is open until 2am every night. You can chat with locals over a cocktail, like the Trophy Wife, a passion fruit and elderflower laced vodka. The adjacent Berkeley Perk Café serves cooked items, such as breakfast tacos and omelettes.

Leisure and Activities

Guests can perk up with a cup of coffee and one of Staypineapple's signature pineapple treats. The hotel provides help-yourself coffee in the lobby, where a couple of bright yellow bikes stand ready for guest's use. Those bikes mean all the city's sites are just a few pedals away with fun beach cruisers. Enjoy high-definition TVs with streaming capability to stream movies when you're not out exploring the city.

Location: South End

Staypineapple, A Delightful Hotel, South End is 0.5 km from Back Bay, 3 km from Beacon Street, and 0.5 km from Arlington. The hotel sits in the charming South End, a neighborhood with great dining. The central location on the border of Back Bay and South End means you're just a short walk or cab ride away from a memorable dinner or Red Sox game. The hotel is near the summer-to-December SoWa Open Market, which has artist and vintage wares, and SoWa First Fridays, an art market held on the first Friday of every month.

Services and Amenities

Staypineapple provides unequaled hospitality and stylish furnishings. The hotel is smoke-free. High-speed wireless Internet access is available on unlimited devices. Guests can enjoy daily Afternoon Delights, offering coffee and signature pineapple treats in the lobby. The hotel provides a reusable PATH water bottle pre-filled with purified still drinking water. Guests can refill their water bottle with cold, hot, still or sparkling water at the Water Bar in the lobby. The hotel offers pineapple bikes for guest use. It also offers Quick Bites & Bevvies, with a variety of snacks along with locally sourced craft beer, wine and other refreshments. A work desk and telephone with access to the 24-hour front desk are provided for guest convenience.

“Staypineapple distinguishes itself with quirky charm and a prime South End location near Back Bay; I especially appreciate the hotel's embrace of its playful pineapple theme. The Naked Experience, with its European-style duvets, enhances the comfortable, modern guest rooms. Add in the convenience of complimentary bikes and the pet-friendly vibe, and you've got a memorable Boston stay.”
Hotel logo
James DavidEditor-in-Chief at Tohotel
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Select your room type

The hotel 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
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

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free 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

Trophy Room presents a vibrant American dining experience that captures the essence of local flavors and beloved classic dishes. Set in the heart of the modern South End, it offers a cozy atmosphere perfect for a leisurely brunch or an intimate dinner.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

American
Ambiance
Modern setting with a warm and inviting atmosphere, ideal for both casual gatherings and special occasions.
Key Offerings
Features indulgent options like avocado toast topped with braised tomatoes and goat cheese, perfect for brunch. Dinner offerings highlight seasonal specialties, ensuring a delightful dining experience.
Reservation
Recommended for dinner, especially on the weekends.
Open for brunch on Sundays 12:00 - 20:00, and for dinner from Wednesday to Saturday 16:00 - 00:00.

Location

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
Local Highlights Near Staypineapple
Top Attractions
Activities
Dining
Entertainment
Boston Common
Boston Common
15 minutes' walk
Boston's oldest public park offers beautiful landscapes, walking paths, and seasonal events, perfect for relaxation and picnics.
Freedom Trail
Freedom Trail
16 minutes' walk
A 2.5-mile path through historic sites, the Freedom Trail showcases Boston's rich history with guided tours and self-exploration options.
Newbury Street
Newbury Street
15 minutes' walk
Fashionable street lined with boutiques, cafes, and galleries, ideal for shopping, dining, and enjoying vibrant street life.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Showcases an impressive collection of artwork across various periods, offering insight into global culture and art history.
Boston Biking Tours
15 minutes' bike ride
Guided biking tours through historic neighborhoods provide a mix of adventure and insights into Boston's past. Rentals are available.
Yoga at the Park
15 minutes' walk
Outdoor yoga sessions in Boston Common offer relaxation with stunning views. Classes cater to all levels and often require booking.
Kayaking on the Charles River
20 minutes' walk
Kayak rentals are available for a fun adventure on the Charles River, providing beautiful views of the Boston skyline.
Masa
Masa
3 minutes' walk
Offers a lively atmosphere with Southwestern cuisine, featuring a variety of enchiladas and unique margaritas. Reservations recommended.
The Trophy Room
The Trophy Room
1 minute' walk
Casual spot serving American comfort food and cocktails; known for its vibrant decor and lively atmosphere. Family-friendly options available.
Bootleg Special
Bootleg Special
3 minutes' walk
Gastro pub with a creative menu highlighting local ingredients; offers craft beers and a cool setting for casual dining.
Skywalk Observatory
Skywalk Observatory
14 minutes' walk
An observatory offering panoramic views of Boston, complements visits with audio tours and exhibitions. Family-friendly experiences available.
The Wilbur Theatre
15 minutes' walk
Historic theater featuring a variety of live performances, from comedy to concerts. A vibrant venue for enriching nightlife experiences.
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
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
Questions of the users
About Staypineapple, A Delightful Hotel, South End
Is there a nearby parking option for guests, and what are the associated costs?
10 November 2024
There is a parking garage located at 100 Clarendon Street, which charges $36 per night.
Can you tell me the name of the closest parking garage?
15 November 2024
The nearest parking facility is called Clarendon Garage.
Is it possible to store my luggage before check-in or after checking out?
12 October 2024
Yes, there is a secure luggage storage area available for guests to use.
Are elevators available in the hotel for easy access to all floors?
25 October 2024
Yes, there is an elevator that services all floors of the hotel.
What is the Naked Experience, and how does it enhance my stay?
2 December 2024
The Naked Experience offers a cozy and luxurious sleeping environment, featuring freshly laundered bedding and cloud-like European-style duvets.
Is Wi-Fi provided in guest rooms, and are there any laundry services available nearby?
17 January 2025
Wi-Fi is available throughout the property, including all rooms. While there are no laundry or dry cleaning services on-site, there are several options nearby you can utilize.
Does the hotel allow dogs, and are there any fees associated with their stay?
5 February 2025
Yes, the hotel is dog-friendly and has a nightly pet fee of $25 plus tax. This fee includes amenities such as a dog bed and treats.
Are there any breakfast services or arrangements available at the hotel?
15 March 2025
Currently, the hotel does not offer a continental breakfast as the onsite restaurant is closed. However, there are several breakfast spots nearby.
What transportation options are suggested for getting to the airport from the hotel?
18 March 2025
Ride-share services like Uber or Lyft are the most convenient ways to reach the airport from the hotel.
Do the guest rooms feature private bathrooms?
25 March 2025
All guest rooms are equipped with private bathrooms for added convenience.
Why has the room rate changed since my last check?
30 March 2025
Room prices fluctuate daily based on demand and availability.
Can I add another name to my existing reservation?
7 April 2025
Yes, it is possible to add a name to the reservation at your request.
Is it possible to access hot water from the in-room coffee machines?
10 April 2025
Yes, the in-room Keurig machines can also provide hot water if used without a coffee pod.
Are microwaves and mini-fridges available in guest rooms?
18 April 2025
Currently, the hotel does not provide microwaves or mini-fridges in the rooms, but there are convenient dining options at the lobby restaurant.

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