50-100 Rooms
•1 Restaurant
•26 Chandler St, Boston, MA 02116, USA
About this Property
What you'll experience:
Step into a boutique hotel in Boston's South End where playful design meets genuine comfort, all within walking distance of some of the city's best-known sights.
Naked Experience Bedding - Sink into plush, all-white duvets and premium linens built for a deep night's sleep.
South End Location - Wake up steps from art galleries, cafes, and historic Victorian brownstones.
Signature Staypineapple Amenities - Enjoy thoughtful in-room touches that make the space feel personal, not generic.
Walkable to Back Bay - Cross into one of Boston's most stylish shopping and dining districts in minutes.
Award-Winning Design - Stay in a space recognized for its style, comfort, and attention to detail.
Why we love it for your Boston getaway:
Prime South End Address - Puts you closer to the city's culture and food scene than most downtown hotels.
Boutique-Sized Comfort - Skip the crowds and lines that come with larger chain hotels.
Historic Neighborhood Charm - Surrounded by architecture and streets with real character, not corporate sameness.
Flexible Stay Length - Book with no minimum night requirement, ideal for quick trips or extended stays.
Rate Starting at $220/night - Straightforward pricing with no surprises at checkout.
Rooms are available starting at $220 per night with no minimum stay required, making this a fit for a quick weekend or a longer visit.
Why We Like It For Groups
From
$220/night
Book this hotel
Visit the property’s booking site to check availability and get more information on the property.
Amenities
WiFi
Coffee StationLocation
Boston, MA
About the neighborhood
You're staying in the heart of the South End, a walkable neighborhood known for its art galleries, hip cafes, and rows of Victorian brownstones. Fenway Park and Boston's major historic sites are just a short ride away, putting you close to the action without the downtown noise. When you're ready to wind down, you're minutes from Back Bay's shops and restaurants, then back to your room for a night in the Naked Experience double duvets.
Getting around
The South End is easy to explore on foot, with Back Bay and many of Boston's landmarks within walking distance. Ride-shares and the T are both close by if you'd rather not walk, making it simple to reach Fenway Park or the Freedom Trail. Whether you're on foot or catching a quick ride, you're never far from where you want to be.
Reviews
Frequently Asked Questions
Is Staypineapple Boston pet-friendly?
Absolutely! Staypineapple Boston welcomes pets, including dogs, cats, and other furry or feathered companions. Guests can also take advantage of the Pineapple Pup Package, which includes 50% off the pet fee, plus treats and goodies for your pet.
Is there a restaurant or bar on-site?
Yes! Trophy Room is the hotel’s on-site bar and restaurant, serving all-American classics and creative cocktails in a lively atmosphere. Weekend breakfast is also available. Hours vary throughout the week, so we recommend checking with the hotel for the latest schedule.
Do you offer group booking rates?
Yes! Staypineapple Boston offers group rates for weddings, family reunions, business events, and other group gatherings. Contact the hotel’s sales team to discuss your group’s needs and available rates.
Is there a minimum stay requirement?
No! There is no minimum night requirement, making the hotel a convenient option for both quick weekend trips and longer Boston stays.
What is the hotel close to?
The hotel is located in Boston’s South End, within walking distance of art galleries, cafes, restaurants, and historic Victorian brownstones. Back Bay is also just minutes away, while attractions such as Fenway Park and the Freedom Trail are easily accessible by public transportation or rideshare.
