Call us 24 hours, 7 days
Scoopon
Join now to view
member prices
Premium Collection
Boston, Massachusetts • View on map

Staypineapple, A Delightful Hotel, South End Boston

Vibrant Heritage Stay in South End Boston

8.6
Excellent
From online reviews
Staypineapple, A Delightful Hotel, South End Boston logo

Discover bustling markets, storied sporting grounds, renowned restaurants and revolutionary history from the heart of Boston’s charming ‘Southie’ or “SoBo’ neighbourhood with a stay at the Staypineapple, A Delightful Hotel, South End Boston. This boutique, art-inspired property is an easy walk from iconic landmarks including the Freedom Trail, Boston Common, Chinatown and Newbury Street.

The whimsical Staypineapple Hotels are built as ‘celebrations of the living arts’. The lobby and guest rooms are dotted with beautiful abstract pieces and decorative tiling, with Staypineapple’s signature yellow accents and pineapple logo making a frequent appearance. The chic Trophy Room restaurant and bar is an understated tribute to the city’s sporting prowess and the perfect place to enjoy Sunday brunch or evening cocktails. Combining South Bostonian charm and vibrance with modern chic, thoughtful features and gracious service, all wrapped in the stylish package of a historic building, the Staypineapple, A Delightful Hotel, South End Boston is your inner-city sanctuary.

1 to 31 Nights packages available
Sign up and save up to 16% on this hotel
Join over 8 million global members to unlock our amazing deals & benefits!
More inclusions: Drinks, dining, transfers & more
More options: 1,000s of hotels, tours & flights
More expertise: 24/7 customer service, worldwide
4.7/5
(3K reviews)
Trustpilot
4.8/5
(10K reviews)
Other ways to log in
By continuing, you agree to our Terms & Conditions and Privacy Policy, and to subscribe to marketing communications for offers, alerts and services.
Location

Staypineapple, A Delightful Hotel, South End Boston
26 Chandler St, Boston, MA 02116, United States

Experience Bean Town like a true local at the Staypineapple, A Delightful Hotel, South End Boston. In the hip South End district, this hotel is the ideal launching point for your Boston jaunt, whether you’re taking a stroll along the Freedom Trail, catching a game with one of Boston’s storied teams, exploring Back Bay or scouting out the city’s famous historical sites, stylish boutiques and famed restaurants. The hotel is located approximately a 20-minute drive from Boston Logan International Airport (BOS). Airport transfers are not included in your stay, please plan accordingly.

Need flights? Our dedicated flights concierge can assist with all your flight requirements. Contact sales@luxuryescapes.com.

Facilities

  • Trophy Room restaurant and bar
  • Unlimited bottled water
  • 24-hour front desk
  • Pet friendly
  • Beach cruiser cycles
  • Wi-Fi
  • Check-in: 4pm / Checkout: 12pm

Surcharges may apply to select facilities and services

Fine Print

Package Inclusions: Inclusions are correct at the time of purchase. Refer to your booking confirmation for details. Please note package inclusions for extra guests vary depending on the rate selected, please choose your package carefully.

Dining inclusions do not include beverages (unless otherwise stated). Menus are subject to change without notice.

Please Note: The following applies to select packages only

  • Dining inclusions do not include beverages (unless otherwise stated). Menus are subject to change without notice.
  • The included credit is only valid at Pineapple Quick Bites & Bevvies Cooler and the Trophy Room and must be used during your stay. Any unused credit will be forfeited and cannot be transferred or redeemed for cash.
  • The waved hotel fee covers: high-speed Wi-Fi, STREAMPINEAPPLE streaming service, in-room tea and coffee, unlimited bottled water and access to the hotel’s beach cruisers.

The property, facilities and dining are subject to government regulations and restrictions. Please check the property website for the most up-to-date information as some of the services may be impacted.

Scoopon reserves the right to modify prices for marketing and commercial reasons. Please note that full terms and conditions apply.

Reviews

8.6
Excellent
Reviews from Google
Ron E.
Reviewed 03 Nov 2025
10
This hotel is in a great location for us as it's only a 10 minute walk to daughter's apartment in the South End/Back Bay area. I knew going into the booking that the rooms were smaller, as quite a few city hotels have smaller rooms. The room was smaller but it was well designed with space under the bed and drawers under the bed. Bathroom was small but functional. Towels were high quality and shampoo, conditioner, soap, lotion all nice Tommy Bahama brand. And they even provide a robe. But we did not spend much time in there, except to sleep, shower and go enjoy Boston. Bedding was very comfortable for us. Love the concept of the individual comforter/sheet for each guest. No more stealing of the covers. Staff was so pleasant. Loved the touches of free coffee in the room, water bottle with refillable water (sparking and tap) down in the lobby. I would definitely stay here again. So, thanks for a great stay and we will be back.
Recommends this hotel
10
Javid K.
Reviewed 23 Oct 2025
10
Had a really good experience staying here. The hotel itself was clean and comfortable, but what stood out the most was the staff especially Isa at the front desk. He was super friendly, polite, and always ready to help with anything I needed. You can tell he really cares about making guests feel welcome. Thanks to Isa and the team for making my stay so smooth and pleasant. I’ll definitely come back next time!
Recommends this hotel
10
Euge B.
Reviewed 23 Oct 2025
10
Arriving at STAYPinapple was a relief after a long flight. Mitchell received us with a smile and the warmth of someone who is happy to see you enter the door. He recommended us the best options and was super helpful! Then arriving at the room and finding ourselves with a comfortable space, arranged and where even the smallest detail is designed for the comfort of the guest was fantastic. It is comfortable, and by far it was the best bed in which we rested on every vacation. At night Rashawn is in the lobby and he also gave us spectacular recommendations. The lobby bar has a great menu and the service is magnificent. We can't wait to return!
Recommends this hotel
10
Buster C.
Reviewed 27 Oct 2025
2.0
We checked in and checked out within 15 minutes. The photos make the rooms appear much larger. In reality they are very small. No closets, only wall hooks. Minimal space to walk around the bed. Drawers under the bed are the only storage. The bathroom has a tiny pedestal sink with no counter space at all. The photos do not show the bathrooms accurately. We were in town for a wedding and there was no practical way to get ready in that room. The front desk agent, Reshawn, was professional. Hotels dot com contacted the property and the hotel agreed to cancel the stay and refund the first night since we did not stay. After we left they declined to honor that commitment. Because of this reversal I am compelled to write this review to warn others that the hotel did not follow through on what it promised.
Does not recommend this hotel
2.0
Reviews: 1-4 of 4
Related Travel