Staypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photo

STAYPINEAPPLE, A DELIGHTFUL HOTEL, SOUTH END, Boston

Save up to 10%
by booking directly
compared to Booking.com
Check rooms and rates
From$97 /night
Check-in
12Aug
Check-out
13Aug
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Overview and Details

26 Chandler St, Boston, 02116
-
Close to the Boston Public Garden
Great
8.5
9.0
/10
4.2
4.3
/5

3-star boutique hotel in South End Boston with The Naked Experience

Amenities

Staypineapple, A Delightful Hotel, provides a range of signature amenities that enhance the guest experience. Guests can enjoy The Naked Experience, featuring cloud-like European-style individual duvets and cozy robes for optimal comfort. Daily Afternoon Delights offer pineapple treats and coffee, bridging the gap between relaxation and refreshment throughout the day.

Rooms

Each room is equipped with plush pillow-top beds topped with European-style double duvets for a restful night. The Back Bay King room serves travelers with a spacious walk-in shower and high-definition TV for streaming. Corner rooms provide additional natural light with partial city views, enhancing every stay.

Location

Staypineapple Boston is strategically situated in the South End, adjacent to Back Bay and numerous historical sites. The property is within a short walking distance to Arlington Station, providing direct access to Fenway Park and downtown attractions. Local boutiques, cafes, and restaurants in the South End add to the hotel's prime location.

Pet-Friendly Policy

The hotel welcomes pets with its Pineapple Pup Package, which includes treats and amenities for furry guests. This package ensures pets remain comfortable while enjoying their stay. A collapsible water bowl and dog bed are provided, making it convenient for pet owners.

Dining

On-site dining is available at Trophy Room, known for its all-American favorites and vibrant atmosphere. Guests can enjoy a lively weekend breakfast while savoring original cocktails and familiar classics. Quick Bites & Bevvies offers a selection of snacks and locally sourced beverages anytime.

Highlights

Location: Adjacent to Back Bay and historical sites

Rooms: Each room equipped with plush pillow-top beds

Dining: On-site Trophy Room with all-American favorites

Pet-Friendly: Pineapple Pup Package with treats

Bikes: Stylish bikes available for city exploration

Must-do experiences

  • Stroll along the historic Freedom Trail for a slice of American history.
  • Indulge in a lobster roll at James Hook & Co. for local flavors.
  • Visit the Isabella Stewart Gardner Museum for stunning art and gardens.
  • Explore the bustling Boston Public Market for local crafts and food.
  • Catch a game at Fenway Park for an unforgettable sports experience.

Choose Your Room Category

The hotel offers a range of accommodations including doubles, family rooms, and suites—plus breakfast, free cancellation, and special rates.
South End Corner King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower
Back Bay King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower

Room Availability and Pricing Calendar

Find available rooms and check today's best prices!
August 2026 - August 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
August 2026
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
September 2026
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
October 2026
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
November 2026
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
December 2026
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
January 2027
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
March 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
April 2027
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
May 2027
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
June 2027
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
July 2027
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
Choose dates to see prices
Check-in/ Check-out

Facilities

This hotel provides premium amenities for a memorable and relaxed stay
Facilities: Great
8.3/10Review 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 the vibrant flavors of American cuisine at the Trophy Room, where modern decor meets a casual atmosphere. Enjoy a delightful brunch or dinner while surrounded by the charm of the lovely South End neighborhood.
  • Trophy Room

    American
    Ambiance
    Modern with a welcoming vibe
    Key Offerings
    Signature dishes include rich avocado toast with braised tomatoes and goat cheese, paired with a selection of craft cocktails. Enjoy the charm of South End's trendy neighborhood while dining.
    Reservation
    Recommended
    Wednesday to Saturday: 4:00 PM - 12:00 AM; Sunday: 12:00 PM - 8:00 PM.

Location

26 Chandler St, Boston, 02116
Explore Boston
Explore Boston's Best
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
Boston Common
15 minutes' walk
The oldest public park in the U.S., featuring lush landscapes and walking paths, perfect for a relaxing stroll.
Freedom Trail
Freedom Trail
16 minutes' walk
A historic 2.5-mile route showcasing Boston's significant sites, ideal for history enthusiasts and guided tours.
Museum of Fine Arts
Museum of Fine Arts
25 minutes' walk
Home to an extensive collection of artworks, this museum offers guided tours and free admission on designated days.
Faneuil Hall Marketplace
Faneuil Hall Marketplace
25 minutes' walk
A vibrant marketplace featuring shops and eateries, where you can enjoy street performances and seasonal events.
Yoga at Boston Common
15 minutes' walk
Outdoor yoga sessions held in the park, offering relaxation amidst nature for all skill levels; check for seasonal offerings.
Biking the Esplanade
10 minutes' drive
Rent a bike and explore the scenic Charles River Esplanade, perfect for thrill-seeking cyclists; rental services available nearby.
The Trophy Room
1 minute' walk
A casual eatery with an American menu; try the signature burgers and local brews. Reservations recommended during peak times.
Masa
3 minutes' walk
A vibrant atmosphere featuring Southwestern cuisine; known for its margaritas and fresh ingredients. Dietary options available.
Laugh Boston
10 minutes' drive
Comedy club featuring national headliners and local talent; family-friendly shows available. Reservations are advised for popular nights.
House of Blues
15 minutes' walk
Live music venue with a lively atmosphere; hosts a variety of musical acts and themed nights. Perfect for all ages.
Navigating city
  • City Centre
    Boston 20 min  ·  1.0 mi
  • Airports
    Logan (BOS) 13 min  ·  5.3 mi
    Worcester Regional (ORH) 116 min  ·  47.7 mi
  • Train
    Boston South Station 17 min  ·  4600 ft
  • Underground
    Back Bay Metro Station 5 min  ·  1400 ft
  • Bus
    Bus stop 2 min  ·  400 ft
Want Access to Early Bird Booking Discounts?
Unlock Exclusive Savings Instantly!
Check Rates
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 and Hotel Ratings

Honest Guest Feedback Based on Real Stays
Review score
Based on 765 verified reviews
8.6 /10
Great
84 %
Recommend
Breakfast
8.3/10
Cleanliness
8.9/10
Comfort
8.7/10
Facilities
8.3/10
Free WiFi
7.7/10
Location
9.1/10
Paid Wi-Fi
8.6/10
Staff
9.1/10
Value for money
8.1/10
Pros
Good location
Wonderful staff
Comfortable bed
Cons
Small rooms
Guest reviews
based on 61 reviews
3.5/5
based on 851 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.
Open reviews
Questions of the users
About Staypineapple, A Delightful Hotel, South End
Are there any parking options available in the vicinity of the hotel, and if so, what is the cost?
10 November 2024
A recommended parking option nearby is the Clarendon Garage at 100 Clarendon Street, which charges $36 per night.
Does the hotel provide a luggage storage service for guests before check-in or after check-out?
12 December 2024
Guests can store their luggage in a secure area prior to checking in or after checking out.
Is there an elevator in the hotel for easy access to different floors?
5 January 2025
Yes, the hotel is equipped with an elevator for guest convenience.
What does the term 'Naked Experience' refer to, and what can guests expect from it?
15 February 2025
The Naked Experience offers a cozy, luxurious night's sleep with freshly laundered bedding and cloud-like European-style duvets.
Can guests rely on Wi-Fi access during their stay, and is there any laundry service available nearby?
20 March 2025
High-speed Wi-Fi is available throughout the hotel, including in all rooms. Laundry services are accessible from nearby providers.
Is the hotel welcoming to guests traveling with pets, and what are the associated fees?
25 April 2025
The hotel is dog-friendly and charges a pet fee of $25 per night, which includes amenities such as a dog bed and treats.
What is the breakfast arrangement for guests during their stay?
30 May 2025
Currently, the hotel does not provide a continental breakfast, but several local restaurants nearby offer breakfast options.
What is the best way to reach the airport from Staypineapple?
5 June 2025
Ride-share services such as Uber or Lyft are recommended for convenient transportation to the airport.
Are the bathrooms in the guest rooms private, or are they shared?
10 July 2024
All rooms feature private bathrooms for the comfort and privacy of guests.
What amenities are provided in the bathrooms, specifically concerning hair dryers?
15 August 2025
Every room is equipped with a blow dryer for guest convenience.
Is there a facility to prepare hot beverages like tea in the rooms?
20 September 2025
Keurig machines in the rooms can produce hot water, allowing guests to enjoy tea or coffee at their convenience.
Can a name be added to an existing reservation if needed?
25 October 2025
Yes, it is possible to add a name to an existing reservation.

Next best alternative

Consider them for your next trip.