Is there a parking option nearby, and what are the costs associated?
01 November 2024
There is a parking garage located at 100 Clarendon Street, with an overnight rate of $36 plus taxes. 74 photos
STAYPINEAPPLE, A DELIGHTFUL HOTEL, SOUTH END, Boston – Your ideal downtown stay
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Key details
Hotel Overview
26 Chandler St, Boston, 02116,
- Close to Copley Square
Great
8.5
9.0
4.1
4.3
Staypineapple, A Delightful Hotel, South End - Modern hotel with The Naked Experience near Back Bay
Located on the border of Back Bay and South End, Staypineapple Boston offers a central location within walking distance of historical sites, restaurants, and Fenway Park. The hotel features The Naked Experience, which includes European-style duvets, cozy robes, and oversized towels. Guests have access to high-speed Wi-Fi, designer bath products, and in-room Keurig coffee makers. The Trophy Room bar serves cocktails like the Trophy Wife (vodka with passion fruit and elderflower) and is open until 2am daily. The adjacent Berkeley Perk Café provides breakfast options like omelets and tacos. The hotel is steps from the SoWa Open Market and SoWa First Fridays art market.
Additional perks of the hotel
Free lobby coffee and pineapple treats in the afternoon
Complimentary use of yellow beach cruiser bikes
Reusable PATH water bottles with refill stations in the lobby
Dog-friendly accommodations with Pineapple Pup Package available
24-hour front desk service and streaming-capable HDTVs in rooms
Rooms
All rooms include plush pillow-top beds with European-style double duvets, high-speed Wi-Fi, and designer bath products. The Back Bay King features a king-size bed and walk-in shower. The South End Corner King offers additional natural light and partial city views. Rooms are equipped with 50-inch HDTVs with streaming capability, iPod docking stations, and work desks. Charging points are integrated into bedside tables with crystal lamps.
Other conveniences
Marble-tiled bathrooms with walk-in showers
Signature lightweight robes
Unlimited in-room Keurig coffee and tea service
Ironing facilities and air conditioning
Flat-screen TVs with streaming services
Must-do experiences
- Visit the Boston Tea Party Ships for a fun, historical reenactment.
- Try a classic lobster roll at Neptune Oyster in the North End.
- Stroll through the hidden Arnold Arboretum for serene nature trails.
- Explore the exhibits at the Isabella Stewart Gardner Museum.
- Don't miss the vibrant Boston Public Market for local artisan foods.
Choose Your Room
Our listed hotels offer a variety of room types—double rooms, family suites, or deluxe options—all with features like breakfast, flexible cancellation policies, and exclusive deals.
South End Corner King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower
room details
Back Bay King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower
room details
Room Rates & Availability Tracker
Find Deals for Your Travel Dates
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Check-in/ Check-out
Amenities
Thoughtful hotel amenities for a comfortable stay
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
Staypineapple, A Delightful Hotel, South End offers a distinctive dining experience that captures the essence of modern American cuisine. Guests can savor dishes prepared with care in a stylish, inviting ambiance that reflects the vibrant spirit of the charming South End neighborhood.
Location
26 Chandler St, Boston, 02116,
Explore Boston
Local Highlights
Boston Common
15 minutes' walk
A historic park featuring scenic paths and the iconic Frog Pond; perfect for family picnics and seasonal events.
Museum of Fine Arts
25 minutes' walk
Housing an extensive art collection from around the world; offers special exhibitions and free admission days.
Faneuil Hall Marketplace
25 minutes' walk
A vibrant market with shops and eateries, famous for street performances and local foods; vibrant atmosphere every day.
Freedom Trail
16 minutes' walk
A 2.5-mile historic walking trail featuring significant sites from the American Revolution; guided tours available.
Biking the Charles River
15 minutes' walk
Enjoy scenic views overlooking the river with bike rentals available nearby; a rejuvenating experience for all.
Boston Tea Party Ships & Museum
25 minutes' walk
An interactive experience where visitors can relive the famous event; includes guided tours and historical reenactments.
The Trophy Room
1 minute' walk
An upscale pub atmosphere offering comfort food and craft cocktails; ideal for casual meals or special occasions.
Wink & Nod
2 minutes' walk
A speakeasy-style bar with innovative cocktails and small plates; a cozy spot for date nights or laid-back gatherings.
House of Blues
15 minutes' walk
A renowned live music venue featuring performances across genres; check the schedule for all-ages shows.
The Wilbur Theatre
25 minutes' walk
Historic theater hosting comedy, live music, and performances; offers a captivating experience in an elegant setting.
Transportation Tips
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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
Guest Reviews & Ratings
What Guests Are Saying?
Show moreShow less
Pros
Comfortable bed
Clean room
Perfect location
City view
Modern concept
Cons
Poor temp regulation
Small bathroom
Cannabis smell
Guest reviewsbased on 725 reviews
Sophia from United Kingdom
Couple
South End Corner King
3 nights in November 2025
|
Reviewed: January 29, 2026
9.0/10
good stay
helpful staff pineapple decor reusable bottle
the staff was amazing and the location is superb, very close to various points of interest. i found the pineapple decor throughout the hotel to be very cute. the provided reusable water bottle was a great initiative, and i used the refilling station in the lobby.
the amenity charge felt a bit unnecessary, as its purpose wasn't immediately clear.
Rooms
9/10
the room was of good size and super tidy. there was a king-sized bed with nice bedding. soft, yellow robes were available. i did appreciate the pineapple themed decorations.
Facilities
8/10
The hotel offers free bicycle rentals, a great way to see the city. i noticed the lobby had a water refilling station, which promotes sustainability. the hotel features a bar, offering live music. Desk staff were helpful too.
Dining
10/10
the hotel includes a bar, named Trophy Roomwith some nice options. a keurig coffee maker was available in my room. the bar features friendly bartenders. the pizzas have delicious crust.
Location
9/10
the location is walkable to restaurants and attractions. the hotel sits in a gay-friendly neighborhood. the area is residential and quiet. it's close to subway stations.
0 Helpful
|
william from united kingdom
Couple
back bay king
3 nights in November 2025
|
Reviewed: January 27, 2026
6/10
cramped room infrequent housekeeping
the location was convenient, near the south station.
The room felt cramped (especially the bathroom). The small size made it difficult to move around comfortably. Housekeeping was only every other day, annoying since i prefer daily service.
0 Helpful
Christian from Germany
Single
South End Corner King
3 nights in November 2025
|
Reviewed: January 07, 2026
9.0/10
really good stay with good touches
friendly staff clean room awesome amenities convenient location
I've never felt so welcome at a hotel. the staff was friendly and helpful, especially with local recommendations. the room was clean and well-kept. The amenities were great. i liked the complimentary coffee and tea station in the lobby. the location WAS very convenient for exploring the city. i had easy access to public transportation and nearby attractions.
the room size was somewhat smaller than expected, and storage space was limited
Service
9/10
the front desk staff was always available. they gave prompt assistance with any request. daily housekeeping kept the rooms tidy and well-stocked, and everyone maintained a professional demeanor.
Dining
8/10
the hotel bar provided several drink choices. the restaurant offered a solid menu for both dinner and breakfast. i found the quality of the food was consistent, and there was availability of seating.
Location
10/10
the hotel is near many local attractions. there are several restaurants and shops within short walking distance. public transportation stops are very accessible, and the area is pretty safe to walk around in.
Rooms
9/10
the room had modern décor and functional design. the bed was very comfortable, with soft linens. the bathroom included quality toiletries. the air conditioning worked very effectively and quietly.
0 Helpful
|
Show more reviews
Questions of the users
About Staypineapple, A Delightful Hotel, South End
Can luggage be stored before check-in or after check-out?
05 January 2025
A secure area is available for guests to store their luggage before check-in and after check-out. Are elevators available in the hotel for easy access?
12 February 2025
Yes, there are elevators throughout the hotel for guest convenience. What is the 'Naked Experience' at Staypineapple all about?
20 March 2025
The Naked Experience promises a cozy, luxurious night with freshly laundered bedding and cloud-like European-style duvets for a restful sleep. Is Wi-Fi available in the hotel for work-related needs?
23 April 2025
Wi-Fi is available throughout the hotel and in all guest rooms for your connectivity needs. Is the hotel accommodating to pets?
30 May 2025
The hotel is pet-friendly with a nightly fee of $25, which includes a dog bed, treats, waste bags, and bowls. Are there breakfast options available near the hotel?
15 June 2025
While the on-site restaurant is currently closed for breakfast, there are several nearby restaurants that serve breakfast. How can guests reach the airport from the hotel?
22 July 2025
Ride-share services like Uber or Lyft are convenient options for getting to the airport. Do all rooms have private bathrooms for guest convenience?
09 August 2024
Yes, each room is equipped with a private bathroom ensuring comfort and privacy. Are coffee and tea making facilities available in the rooms?
03 September 2025
In-room Keurig machines are provided, which can also dispense hot water for tea, along with various coffee options. Is there a way to include additional names on an existing reservation?
14 October 2024
Adding a name to an existing reservation is possible and easily arranged.Next best alternative
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