Staypineapple, A Delightful Hotel, South End Boston

ex. Chandler Inn Hotel
Boston, United States View on map
8.4 Very Good Based on 807 reviews
Editor's Pick

"Bicycles sit in the lobby for guest use alongside a station offering hot, cold, and sparkling water. Rooms feature individual European-style duvets and the Trophy Room restaurant serves American fare. Squarely aimed at city explorers, much less at those sensitive to noise."

from US$ 115 US$ 97 per night
Save 15%
Check-in
15 Nov 2026
Check-out
16 Nov 2026
Guests
2 guests

Adults:

2

Children:

0
  • Free cancellation
    on many rooms
  • No booking fees
    Pay at the hotel
  • Secure booking
    Your data is safe
  • Best price guarantee
    Found a better price?

Why guests choose Staypineapple, A Delightful Hotel, South End

  • Naked Experience
    European twin duvets
  • Dog-Friendly
    Beds, bowls & treats
  • Complimentary Bikes
    Explore Boston
  • Trophy Room
    All-American menu & cocktails
  • CORE Welcome Drink
    House wine, beer, or non-alcoholic
  • Water Bar
    Still, sparkling, hot & cold

Overview

Offering a restaurant, the comfortable Staypineapple, A Delightful Hotel, South End Boston lies in the Newbury Street district, 0.5 miles from the esteemed Boston Public Library and approximately 25 minutes' walk from The Institute of Contemporary Art. The hotel provides guests with Wi-Fi throughout the property.

Situated merely 0.7 miles from the central Boston Common Public Park, the smoke-free hotel also gives access to such sports venues as the baseball stadium "Fenway Park", which is 1.4 miles away. The 4-star Staypineapple, A Delightful Hotel, South End Boston is around a 5-minute stroll from Back Bay Sta - Inbound bus stop and fairly close to the graceful Arlington Street Church. Nature lovers will enjoy the vicinity of Beacon Hill, located miles away. Wang Theater is also situated just 9 minutes by foot from the accommodation. Boston South train station is in the immediate vicinity of the Staypineapple, A Delightful Hotel, South End, while Back Bay subway station is 0.2 miles away.

The rooms feature tea and coffee-making facilities, as well as a flat-screen TV with satellite channels for your convenience.

The Boston hotel invites guests to have a drink at a coffee bar. It also features a lounge area for guests' comfort. The Berkeley Perk Cafe is in close proximity to this property.

  • Check-in
    from 16:00 until 23:59
  • Check-out
    until 12:00
  • Hotel class
    4 stars
Staypineapple, A Delightful Hotel, South End
Our tips

Should you book Staypineapple, A Delightful Hotel, South End?

Perfect if you
  • Are traveling with a pet - the hotel offers specialized dog amenities including dog beds and treat options.
  • Want to explore Boston on two wheels with complimentary cruiser bicycles available for guest use.
  • Enjoy a lively bar and restaurant - the on-site Trophy Room serves brunch and dinner in a modern American setting.
Maybe skip if you
  • Need free on-site parking - the hotel has minimal parking options and charges a daily amenity fee that does not include parking.
Best for
  • A fun, quirky pineapple-themed room decor with a stuffed animal adoption program benefiting local shelters.

Facilities of Staypineapple

General
  • No smoking on site
  • Wi-Fi
  • 24-hour reception
  • Pets allowed
  • Luggage storage
  • Lift
  • Smoke detectors
  • Fire extinguishers
  • Key card access
Dining
  • Restaurant
  • Bar/Lounge area
Staypineapple Guest Services
  • Pet amenities available
Room Amenities
  • Air conditioning
  • Heating
  • Tea and coffee facilities
  • Flat-screen TV

Policies

Staypineapple, A Delightful Hotel, South End applies these conditions to all bookings.
Check-in / Check-out
Check-in
from 16:00 until 23:59
Check-out
until 12:00
Important info
  • Children and extra beds
  • There are no cribs provided in a room.

Frequently asked questions

During your stay at Staypineapple, A Delightful Hotel, South End, you can dine at Trophy Room restaurant which serves American dishes.
Staypineapple, A Delightful Hotel, South End is just a stone’s throw away from the city’s key locations and sites, including Emmanuel Church and Copley Place.
To rent a room in Staypineapple, A Delightful Hotel, South End Boston you will need to spend about $205.
Guests of Staypineapple, A Delightful Hotel, South End will reach the downtown within 20 minutes' walk.
Logan is the closest airport and it is situated within 0.5 miles from Staypineapple, A Delightful Hotel, South End Boston.
Popular spots near Staypineapple, A Delightful Hotel, South End include Newbury Street, Government Center, John Hancock Tower, among others.
Restaurants near Staypineapple, A Delightful Hotel, South End Boston include Cosmica and Berkeley Perk Cafe.
At Staypineapple, A Delightful Hotel, South End you can pay with Mastercard, Visa and American Express as well as other payment methods.
Some rooms of Staypineapple, A Delightful Hotel, South End welcome guests with the following facilities:
  • ironing facilities
  • smoke detectors
  • a separate toilet
  • an electronic key card
.
Guests are welcome to stay at Staypineapple, A Delightful Hotel, South End Boston with their pets.
Yes, Staypineapple, A Delightful Hotel, South End does offer bag storage.

Thank you for your feedback

Thank you for subscribing

Close
Check-in
15 Nov 2026
Check-out
16 Nov 2026
Guests
2 guests

Adults:

2

Children:

0
Select the dates
to see the actual offers