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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
Molly C.
Reviewed 03 Oct 2025
10
We had a great stay! Location and amenities were perfect. When we travel back to Boston, we’ll be staying at Staypineapple again.
Recommends this hotel
10
Lian F.
Reviewed 02 Oct 2025
10
What a great concept. They think of things other hotels don't. Not cheap but worth a stay. Bar is a great place to hang out.
Recommends this hotel
10
Ali F.
Reviewed 29 Sep 2025
10
Mitchell went out of his way to be helpful. I highly recommend staying at this hotel.
Recommends this hotel
10
Giacomo P.
Reviewed 04 Oct 2025
8.0
A unique hotel, entirely pineapple-themed. The bed was very comfortable, but the single window wasn't soundproof, was drafty, and let in too much light in the morning. Excellent location for visiting Boston.
Recommends this hotel
8.0
Reviews: 1-4 of 4
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