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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
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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
Karen H.
Reviewed 02 Aug 2025
10
My husband and I stayed three nights to attend a couple of concerts at TD Garden. This was the perfect home base for us. The rooms were small, but clean. The bed was super comfortable and they provided us with a refillable water bottle that could be refilled in the lobby at any time. The only thing that could have added to our experience was if they added a small refrigerator in room to keep drinks cold. They also give you a token to get a free soda, beer or wine at the Trophy room, their bar/restaurant. We ate there one night and it was a great place to relax and get a bite to eat and drink. The staff were very friendly and helpful. I want to give a shout out to the maintenance man. As we were getting ready to check out, we had a stressful situation happen at home. In our hurry to leave, I left my phone in the room. Just as I had realized it when I stepped outside, the maintenance man was chasing me down to return it. We will definitely stay here again when we visit Boston!
Recommends this hotel
10
Nick G.
Reviewed 21 Jul 2025
10
We loved the location as well as amenities of this hotel. The rooms were small but cozy. Bed was really comfortable and the AC was cold which was great because there was a heatwave in Boston when we were staying there. Loved the trophy room downstairs for cocktails and a place to meet friends. Would recommend.
Recommends this hotel
10
Caitlyn H.
Reviewed 25 May 2025
10
This hotel was in a wonderful location for getting around to the sites in Boston. It is definitely walkable to many things and close to a few T stops. Due to nature of the hotel being in a big city, the rooms and bathrooms are smaller but the Back Bay King worked perfectly for my husband and me. The theme and aesthetic are well executed. The robe was comfy and a nice addition while getting ready or winding down at night. The attached bar is nice to have as they do have food so on a rainy night we didn’t have to venture out. The front desk staff was nice and helpful when we had questions. They do allow you to store your bags if you arrive before check-in. I would definitely stay here again or another StayPineapple in a different city.
Recommends this hotel
10
beth c.
Reviewed 29 Jul 2025
8.0
Pros: Relaxed atmosphere - nice change from large, chain hotels, friendly staff, very dog friendly, great location for exploring the beautiful South End and the whole downtown, great shower water pressure. Cons: microscopic bathroom (so small I had to stand in the doorway to open the shower door), great view from my upgraded room could not be seen due to a damaged window.
Recommends this hotel
8.0
Reviews: 1-4 of 4
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