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
97US$
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Key details
Hotel Details
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
- Near the Freedom Trail
Great
8.5
9.0
4.1
4.2
Loved by Staypineapple, A Delightful Hotel, South End guests
"The bed was very large with separate duvets for each person."
"Loved the dogs!!"
"All guests get a free drink when they check in!"
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.”
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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
195 sq. feet
1 King-size bed
Shower
Coffee machine
room details
Back Bay King
2 persons
195 sq. feet
1 King-size bed
Shower
Coffee machine
room details
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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
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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.
Staypineapple, A Delightful Hotel, South End Location
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
Map view
26 Chandler St,
Boston,
Massachusetts,
United States,
02116,
Massachusetts
City landmarks
Stadium
Fenway Park
1.4
mi
Landmark
Boston Common
3900 ft
Market
Faneuil Hall Marketplace
1.4
mi
Park
Boston Public Garden
4100 ft
Landmark
Freedom Trail
4200 ft
Museum
Museum of Fine Arts
1.3
mi
Aquarium
New England Aquarium
1.4
mi
Museum
Museum of Science
1.4
mi
Museum
Boston Tea Party Ships & Museum
1.3
mi
Library
Boston Public Library
2900 ft
Parking area
Skywalk Observatory
3700 ft
Square
Copley Square
2600 ft
Landmark
North End
1.5
mi
Landmark
Freedom Trail walk
1.6
mi
Spa Centre
Newbury Street
3900 ft
Church
Trinity Church
2200 ft
Landmark
Boston Children's Museum
1.5
mi
Cemetery
Granary Burying Ground
5100 ft
Monument
Bunker Hill Monument
2.1
mi
Museum
Isabella Stewart Gardner Museum
1.6
mi
Landmark
Beacon Hill
1.2
mi
Monument
New England Holocaust Memorial
1.3
mi
Museum
The Paul Revere House
1.4
mi
Tower
John Hancock Tower
2100 ft
Landmark
Quincy Market
1.3
mi
Museum
USS Constitution Museum
2.0
mi
Museum
The Institute of Contemporary Art
1.5
mi
Public Building
Old State House
1.2
mi
Theatre
Boston Symphony Hall
5100 ft
Landmark
Back Bay
3100 ft
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 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.
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.
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 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 923 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 stationwelcome drinkprivacy 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 roomstrange 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 bottlerefill stationdrink voucherfriendly 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-incozy feelgreat 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-inadorable waterdog 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
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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