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 by 12:00.
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STAYPINEAPPLE, A DELIGHTFUL HOTEL, SOUTH END, Boston
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Key details
Hotel Details
26 Chandler St, Boston, 02116,
- Near the Freedom Trail
Great
8.5
9.0
4.1
4.3
Staypineapple, A Delightful Hotel, South End - A boutique Boston hotel with European-style bedding, on-site dining, and arts district location
Located in the charming South End neighborhood, this 4-star Boston hotel features The Naked Experience bedding system with cloud-like European-style individual duvets and plush pillow-top mattresses. The Trophy Room restaurant and bar serves American classics until 2 AM, offering signature cocktails like the Trophy Wife with passion fruit and elderflower-laced vodka. Each room comes equipped with a flat-screen TV, iPod docking station, Keurig coffee maker, and designer bath products. Staypineapple provides complimentary bikes for city exploration and hosts daily afternoon treats with coffee in the lobby. The Berkeley Perk Café serves breakfast items including tacos and omelets. The property features genuine vintage elements like the original black painted iron staircase. Staypineapple, A Delightful Hotel sits on the border of Back Bay and South End, within walking distance to the Freedom Trail and a direct train connection to Fenway Park.
Pros
Daily complimentary afternoon treats and coffee service from 3:30 PM to 6:30 PM
The Water Bar offers unlimited cold, hot, still, and sparkling water refills
Access to the summer-to-December SoWa Open Market and monthly SoWa First Fridays art market
Corner rooms feature additional natural light and partial city views
Cons
1 mile distance to New England Aquarium and Faneuil Hall Marketplace
Limited on-site breakfast options with only café service available
“Located where South End meets Back Bay, this boutique hotel stands out with its playful pineapple theme and genuinely vintage details. The Naked Experience bedding promises comfort, while complimentary bikes add an element of fun, casual exploration to the Boston visit. The on-site Trophy Room ensures a lively dining scene, making this a practical choice for those who appreciate character.”
Select room type
Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, 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
Check Availability & Prices
Find the best rates for your travel dates now!
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Check-in/ Check-out
Facilities
Hotel has comfortable rooms, premium services, and a prime downtown location
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 in South End, indulge in a culinary experience that embraces the heart of American fare. With a modern atmosphere and thoughtfully crafted dishes, dining here is a celebration of local flavors nestled in the vibrant neighborhood.
Location
26 Chandler St, Boston, 02116,
Explore Boston
Explore the South End
Boston Common
15 minutes' walk
The nation's oldest public park offers scenic paths, historic statues, and lush lawns ideal for relaxation and picnicking.
Museum of Fine Arts
25 minutes' walk
Home to an impressive collection of art from around the world, the museum hosts special exhibitions and free admission days.
Faneuil Hall Marketplace
25 minutes' walk
A bustling market with shops, eateries, and street performances, perfect for experiencing Boston's vibrant culture and history.
Freedom Trail
16 minutes' walk
A 2.5-mile long path dotted with historic sites, this iconic trail offers self-guided tours through Boston's revolutionary past.
Bike Rentals Along the Charles River
20 minutes' walk
Bike rental services near the Charles River provide stunning views and numerous trails for outdoor enthusiasts of all levels.
Spa Treatments at Bella Sante
15 minutes' walk
Indulge in exceptional spa services, offering massage therapies and skin treatments in a serene environment for relaxation.
The Trophy Room
1 minute' walk
An inviting bar and restaurant featuring American comfort food and craft cocktails, perfect for a relaxed evening out.
Masa
3 minutes' walk
Serving inventive Southwestern fare, this lively spot offers a vibrant atmosphere with a blend of delicious flavors.
Cosmica
2 minutes' walk
A contemporary eatery focusing on Mexican-inspired cuisine, known for its fresh ingredients and cozy ambiance.
Boston Symphony Orchestra
20 minutes' walk
World-renowned orchestra offering spectacular performances, from classical to contemporary, in a stunning concert hall.
The Wilbur Theatre
12 minutes' walk
Historic venue featuring a variety of entertainment from comedy shows to concerts, catering to diverse tastes and ages.
Getting around
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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.
Show moreShow less
Pros
Comfortable bed
Friendly staff
Perfect location
Cons
Tiny rooms
Plumbing issues
Guest reviewsbased on 725 reviews
Grace from United States
Couple
Back Bay King
4 nights in November 2025
|
Reviewed: January 29, 2026
8.7/10
Excellent Location and Comfy Robe
convenient refill station welcome drink privacy factor
The hotel offers a water bottle refill station. The welcome drink at check-in was quite refreshing. Housekeeping services are scheduled at the end of each stay, granting additional privacy .
The hotel lacks sufficient soundproofing, I could hear street noises from my room!
Location
9/10
The hotel is within walking distance of various attractions. Several public transportation stops are also conveniently nearby. This provides easy access to different parts of the city and simplifies exploring the area.
Service
9/10
The staff was helpful when I needed assistance. They allowed bag storage before check-in, very convenient. This service enabled me to explore the surroundings freely without worrying about my luggage.
Dining
8/10
The hotel features an attached bar. The bar serves food. This is quite convenient . I could enjoy a meal without having to leave the premises especially useful on rainy evenings.
0 Helpful
|
Matt from United States
Business traveller
Back Bay King
3 nights in November 2025
|
Reviewed: December 10, 2025
6/10
small room strange noises
My room was quite small, and i found it lacking in some essential amenities. There was no closet, only some hooks on the wall, SO it was hard to keep my clothes organized. The bathroom also lacked space. I EXPECTED a bit MORE room to move around. The elevator made some VERY strange noises, causing some concern.
0 Helpful
paul from united kingdom
Couple
south end corner king
3 nights in November 2025
|
Reviewed: November 17, 2025
8.7/10
good south end stay
water bottle refill station drink voucher friendly staff
The complimentary water bottle and refill station were useful. i also appreciated the drink voucher upon arrival at the bar. the location was convenient. I walked to many restaurants. the staff was friendly during check-in and check-out.
the rooms are a bit on the smaller side, though the decor mostly makes up for it.
Location
9/10
the hotel is near many restaurants and shops, with dining and shopping options, and it is convenient for exploring local attractions, though the immediate view isn't the prettiest.
Service
9/10
The front desk staff provided helpful assistance with questions. They also stored my bags since i arrived before check-in. The check-in process was easy, and the staff members were nice to me.
Facilities
8/10
The hotel includes a bar downstairs, with a convenient option for drinks and meals. A water refill station is in the lobby, promoting environmental consciousness. The bar provided great food.
0 Helpful
|
Nico from Germany
Single
Back Bay King
3 nights in August 2025
|
Reviewed: October 05, 2025
9.0/10
Charming Stay in a Great Spot!
simple check-in cozy feel great location
Check-in was simple. A Bernedoodle greeted guests in the lobby. I liked the modern yet cozy feel. The hotel's location made everything easy to reach.
I noticed a very slight draft near the window.
Rooms
9/10
The room had eclectic decor and glam lighting! A pull-up desk counter offered a good workspace. Free water bottles were available, and I could refill mine at the lobby cooler. The robe was soft and a nice addition.
Dining
8/10
The hotel included an attached bar with food service. This was useful on a rainy evening. I didn't need to leave for dinner! The bar saved me from going out.
Service
9/10
The staff at the front desk answered my questions. They also stored my luggage before check-in. This helped me a lot. I could start exploring earlier. The staff was very helpful!
Location
10/10
The hotel is in a quiet area. It is close to a few train stops. Many sites are within walking distance! I could easily reach local attractions.
0 Helpful
|
Aaron from United States
Couple
South End Corner King
3 nights in June 2025
|
Reviewed: June 29, 2025
9/10
early check-in adorable water dog adoption
i found early check-in a real bonus. they provided adorable water bottles made of tin. i noticed they actively support dog adoption, that's a great thing.
i did notice the gym only had a limited amount of equipment.
0 Helpful
Show more reviews
FAQs
About Staypineapple, A Delightful Hotel, South End
How far is Staypineapple, A Delightful Hotel, South End from Fenway Park?
The hotel is approximately 2 km from Fenway Park.
Are there dining options on-site at Staypineapple, A Delightful Hotel, South End?
The hotel features an on-site restaurant, Trophy Room, offering an all-American menu.
What room amenities are provided at Staypineapple, A Delightful Hotel, South End?
Rooms include air conditioning, a flat-screen TV, high-speed Wi-Fi, and designer bath products.
What nearby restaurants can guests find close to Staypineapple, A Delightful Hotel, South End?
Nearby restaurants include Berkeley Perk Café (0.5 km), Masa (0.5 km), and Grill 23 & Bar (0.5 km).
How does the hotel assist guests with local transportation needs at Staypineapple, A Delightful Hotel, South End?
Guests can rent bicycles at the hotel for convenient city exploration.
What is unique about the rooms at Staypineapple, A Delightful Hotel, South End?
The hotel features a unique Naked Experience with cloud-like European-style individual duvets.
What attractions are within walking distance of Staypineapple, A Delightful Hotel, South End?
The hotel is within walking distance to the Freedom Trail and the Back Bay area.
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