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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

•
8.5|Great
Check rooms and rates
From$97 /nightOnly on Our Website -10%
Check-in
16Oct
Check-out
17Oct
Guests
2 Guests
Key details

Property overview

26 Chandler St, Boston, 02116
-
Close to Copley Square
Great
8.5
9.0
/10
4.2
4.3
/5

Rooms

Staypineapple Boston has guest rooms with a flat-screen TV, an iPod docking station, and a work desk. Rooms include plus pillow top beds topped with European style double duvets. The Naked Experience includes cloud-like European-style individual duvets and big thirsty towels. A Keurig machine provides coffee or tea. Guests can stream content on the 50" HDTVs with STREAMPINEAPPLE. Back Bay King rooms feature a king bed and a walk-in shower. South End Corner King rooms offer more natural light and city views.

Dining

The Trophy Room features American cuisine. It serves brunch, dinner, and late drinks. Berkeley Perk Café serves items, such as breakfast tacos and omelettes. The bar is open until 2 AM, serving cocktails like the Trophy Wife. Guests can perk up with a cup of coffee and pineapple treats. Quick Bites & Bevvies offers snacks, beer, and wine. Afternoon Delights in the lobby offers coffee and pineapple treats from 3:30pm - 6:30pm.

Leisure

Guests can use the hotel's bikes. High-speed wireless Internet access is available. Guests can stream their favorite show to the in-room 50" HDTV with STREAMPINEAPPLE. They can also access a water bar in the lobby for water bottle refills. The hotel is smoke-free.

Location

Located in Downtown Boston, Staypineapple is near the Freedom Trail, the Old State House, and Faneuil Hall Marketplace. It is close to the Financial District and City Hall. Fenway Park is 2 km away. Boston Common is 1 km away. The hotel is a short walk or cab ride from Back Bay and the South End. Arlington Station is a 10-minute walk for train access to Fenway Park.

Amenities

The hotel provides a 24-hour front desk and a telephone. Guests receive a reusable PATH water bottle. Guests can use the help-yourself coffee in the lobby. The hotel offers a CORE Welcome Drink with a choice of house wine, beer, or non-alcoholic beverages. High-speed wireless Internet access is available. Each room has a Keurig with custom blended coffee and tea. The hotel is dog-friendly.

“In my opinion, Staypineapple distinguishes itself with its playful pineapple theme and dog-friendly atmosphere. I found the location, bordering Back Bay and South End, especially appealing. Its quirky charm is enhanced by the Naked Experience bedding and complimentary bikes, making it a memorable stay.”
Hotel logo
Harper CollinsEditor, Usboston

Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
Back Bay King
2 persons
195 sq. feet
1 King-size bed
Coffee machine
Shower
South End Corner King
2 persons
195 sq. feet
1 King-size bed
Coffee machine
Shower

Calendar of room availability and rates

See current availability and pricing for your dates
October 2026 - October 2027
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Check-in/ Check-out

Facilities

Amenities are designed to ensure comfort and memorable stays
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

Guest Parking

  • No parking available.

Services

  • Pet amenities available

Dining

  • Restaurant
  • Bar/ Lounge area

Room features

  • Air conditioning
  • Heating
  • Tea and coffee facilities

Media

  • Flat-screen TV
Show more

Dining Onsite

At Staypineapple, A Delightful Hotel in South End, culinary experiences await just steps from the historic heart of the city. The onsite dining options feature modern American cuisine in a vibrant setting, perfect for travelers seeking both comfort and flavor.
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo
Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

Modern American
Ambiance
A chic and contemporary space with an inviting atmosphere, ideal for socializing and relaxing.
Key Offerings
Highlights include delightful brunch options and savory dinner selections, with signature dishes like avocado toast topped with braised tomatoes and goat cheese.
Reservation
Recommended for dinner to ensure a table.
Wednesday to Saturday from 4:00 PM to Midnight, and Sunday from 12:00 PM to 8:00 PM.

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, 02116
Explore Boston
Explore Boston's Best
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
Boston Common
15 minutes' walk
America's oldest public park features lush landscapes and historical significance, perfect for a leisurely stroll or picnic.
Faneuil Hall Marketplace
25 minutes' walk
A bustling hub for shopping and dining, known for its vibrant atmosphere and street performers. A must-visit landmark.
Museum of Fine Arts
25 minutes' walk
Renowned for its vast collection, this museum offers a unique look at art from around the world, with special exhibits often.
Freedom Trail
16 minutes' walk
A 2.5-mile path that connects 16 historical sites, ideal for history enthusiasts and self-guided tours.
Cycle along the Charles River
15 minutes' drive
Bike rentals available near the river, offering scenic views and peaceful pathways for active exploration.
Relax at Boston Public Garden
15 minutes' walk
Stunning flowerbeds and swan boats provide a tranquil escape. Great for picnics or leisurely walks.
The Trophy Room
1 minute walking
Casual eatery with American fare and a friendly atmosphere. Known for burgers and craft beers.
Masa
3 minutes' walk
A trendy Mexican restaurant offering delicious tacos and margaritas in a lively setting. Reservations recommended.
Laugh Boston
15 minutes' drive
A comedy club featuring local talents and headliners, making it a fun night out for all ages.
Royal Boston Theatre
12 minutes' walk
Showcasing various performances from theater to music events. A great spot for family-friendly entertainment.
Local transportation
  • 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
Looking for early booking discounts?
Access special offers today
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 ratings and reviews

Guest feedback from past stays
Cleanliness
8.8/10
Comfort
8.7/10
Facilities
8.3/10
Free Wi-Fi
7.7/10
Location
9.0/10
Staff
9.1/10
Value for money
8.0/10
Pros
Great location
Comfy bed
Helpful staff
Modern bathroom
Good cocktails
Cons
Small rooms
Annoying fees
Guest reviews
based on 61 reviews
3.5/5
based on 818 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
Is there any parking available near the hotel and what can I expect to pay?
21 November 2024
Parking is available at the Clarendon Garage on 100 Clarendon Street for $36 nightly.
Are there any breakfast options available for guests?
15 December 2024
Currently, there is no continental breakfast provided. However, there are various restaurants nearby that serve breakfast.
Does the hotel feature an elevator for guests?
30 January 2025
Yes, an elevator is available in the hotel for guest convenience.
Can guests store their luggage before check-in or after check-out?
10 February 2025
A secure luggage storage area is available for guests both before check-in and after check-out.
Is there Wi-Fi available in the guest rooms, and can I arrange laundry services?
22 March 2025
Complimentary Wi-Fi is provided throughout the hotel and in all guest rooms. However, there are no on-site laundry services, but nearby laundry services can be arranged.
What does the Naked Experience in your hotel rooms entail?
18 April 2025
The Naked Experience offers a unique sleeping experience with freshly-laundered bedding, plush pillows, and luxurious European-style duvets, promoting an incredibly comfortable night's sleep.
What is the minimum age requirement for check-in at the hotel?
12 May 2025
The minimum age for check-in is 18, and guests must present a valid government-issued ID along with a credit card.
Are there any additional charges beyond the quoted rate?
29 June 2025
The total quoted price includes all fees and taxes, with offsite parking being the only additional charge at $40 per night, or $30 with validation.
Is the hotel pet-friendly and what are the related fees?
7 July 2025
Yes, the hotel is dog-friendly, with a nightly pet fee of $25 plus tax. This fee includes amenities like a dog bed and bowls.
How far is the hotel from popular entertainment venues, like Fenway Park?
25 August 2025
Fenway Park is located approximately 2 kilometers from the hotel, making it easily accessible for guests.

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