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Staypineapple, A Delightful Hotel, South End in Boston, MA

26 Chandler Street • Boston, MA 02116
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Corner restaurant with large windows and green double doors, warmly lit inside, located at the base of a multi-story brick building at dusk.
Modern lounge with black-and-white checkered floor, green fireplace, green sofa, glass coffee table, and large windows showing a street view.
Modern bar with high tables and cushioned chairs, a long counter with bottles and glasses, and large mirrors behind the bar. The space is well-lit with round ceiling lights.
Modern hotel room with a large bed, yellow and gray decor, a wall-mounted TV, and a plush dog toy placed on the bed.
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About Staypineapple, A Delightful Hotel, South End Boston

Overview

Staypineapple, A Delightful Hotel, offers a modern boutique escape in the historic South End in Boston. With stylish rooms, signature “Naked Experience” bedding, high-speed WiFi, and pet-friendly perks, this hotel sits steps from Back Bay, Fenway Park, and Boston’s best dining and shopping.

up to 2 people

Good To Know

  • Minimum age to check in is 18.
  • Pet-friendly rooms are subject to fees and availability. See FAQs for details.
  • Features the signature “Naked Experience” bedding for a cozy, restful night’s sleep.
  • HDTVs offer streaming access through StreamPineapple.
  • Complimentary high-speed WiFi available on unlimited devices via SurfPineapple.
  • Afternoon Delights coffee and pineapple treats served daily.
  • Complimentary reusable water bottles and refills available at the Water Bar.
  • The View Boston Observatory is a 10-minute drive away.
  • Fenway Park is a 15-minute drive away.
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Property Amenities

  • 24 Hour Front Desk
  • Elevator
  • Handicapped Access
  • Inside Corridors
  • Bar/Lounge
  • Non-Smoking Rooms
  • Pet Friendly
  • Restaurant on Property
  • Internet Access in Public Areas (free)
  • Concierge Services
  • Breakfast (surcharge)
  • Smoke-free Property
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Promotional Images (27)
Brick building with large windows, warm yellow lights, trees, benches, and potted plants along a quiet street at dusk. Modern hotel lobby with black-and-white checkered marble floor, two yellow bicycles by a staircase, a round reception desk, and decorative writing on the elevator doors. Modern bar interior with a long counter, upholstered bar stools, dining tables, overhead globe lights, and large windows letting in natural light. A modern restaurant interior with green barstools, a marble counter, patterned tile flooring, black-and-white decor, and round pendant lights. Tables and chairs are arranged by large windows. A restaurant interior with a long green tufted banquette, gray chairs, black-and-white checkered floor, and globe pendant lights.

Description

Check-In: 4:00pm Check-Out: 12:00pm
Located in Boston’s South End, Staypineapple, A Delightful Hotel, offers bright pops of color, bold artwork, and signature pineapple touches. Try the Afternoon Delights with coffee and pineapple treats, or the CORE Welcome Drink offering alcoholic and non-alcoholic drinks. At the Water Bar, refill your reusable bottle anytime, one of many eco-friendly touches that make Staypineapple special.

Each guest room features the brand’s famous “Naked Experience” bedding with ultra-soft duvets and European-style sheets, along with high-speed SurfPineapple WiFi on unlimited devices. Unwind with StreamPineapple HDTV for easy streaming, or brew your morning coffee with an in-room Keurig before exploring the city.

If you're travelling with your pets, the hotel provides dog-obsessed service, including plush beds, treats, and bowls for furry companions. Whether traveling for work or play, the hotel’s central location offers easy access to Back Bay, the Prudential Center, Fenway Park, and the Boston Public Garden.

Important Information
  • Parking: The hotel does not have on-site parking. However, there are several nearby garages and metered street parking options. You can use SpotHero app to locate parking spots easily.
  • Pet Policy: Dogs are allowed. The pet fee is USD 29.95 per pet per night. The hotel has no weight limits or breed restrictions. Please notify the hotel directly prior to your arrival date if traveling with a pet. Pet-friendly rooms are limited.

All fees mentioned are subject to change without prior notice and applicable taxes.
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Staypineapple, A Delightful Hotel, South End Boston Reviews

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U8947UMandreash
"Beauticool"
TripAdvisor user rating 4.0 out of 5
Reviewed March 09, 2026 NEW
Rather 4.5 stars. Extremely friendly, helpful & well-informed staff; especially Mitch @ reception desk - thanks for everything! Rooms comparably small but beautiful, nicely equipped & cleverly thought-out. Extremely comfortable bed. Funny pineapplian details, enjoyable extras (refillable, keepable water bottle; free drink …). Bar very busy on Fri/ Sat, however did not hear a sound (on 6th floor) inhouse - but from the outside, as window was not really tight, but fixed provisionally (duct tape did it …) - deducted the 0.5 stars for this. Not located in the midst of everything, but enjoyed the 15 min walking (to Downtown, to Back Bay, …) as part of the experience. As for longer distances, Orange Line (Back Bay) is an easy 5 min walk, even with your larger suitcase. Would definitely choose it again for my next stay in Boston.
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Quest41722357698
"Nice cosy place to stay"
TripAdvisor user rating 5.0 out of 5
Reviewed March 07, 2026 NEW
Cute rooms, close to things you need, attentive staff. Beds are comfy and I really loved visiting Boston and Salem!
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543suee
Buffalo, Erie County, New York
"Fabulous Fun Spot in Boston"
TripAdvisor user rating 5.0 out of 5
Reviewed March 07, 2026 NEW
This is my first time staying here and I promise it is the coolest place from top to bottom. Mitchell greeted me last night and Gabe this morning. Both so welcoming and fun to chat with. I love the decor and the beds are so comfortable. Great bar too! Such a fun atmosphere.
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justinnanookt
"Do not stay in room 701"
TripAdvisor user rating 2.0 out of 5
Reviewed March 02, 2026 NEW
Avoid room 701, the window does not open and there are scratches on the window shade. The side tables are warped and the TV does not work. When asked to switch rooms they did not accommodate. The front desk person was nice but the on site manager in the end wasn’t able to help much.
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paigecX1391UY
"Brilliant do not hesitate to book!"
TripAdvisor user rating 5.0 out of 5
Reviewed February 25, 2026 NEW
Travelled over from Ireland and the minute we put our foot in the door we were greeted with a smile and a warm welcome we had an amazing stay the hotel is beautiful the staff go above and beyond to help could not recommend this hotel more we absolutely loved it location is great and goofy the dog is absolutely gorgeous! The food is great too and reasonably priced We will definitely be back! Paige & James
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Staypineapple, A Delightful Hotel, South End Boston is located at 26 Chandler Street • Boston, MA 02116
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Frequently Asked Questions about Staypineapple, A Delightful Hotel, South End Boston

What is the minimum age to check in?

The reservation holder must be at least 18 years old to check in with a matching, valid, government-issued photo ID and credit card.

Is Staypineapple, A Delightful Hotel, South End Boston pet-friendly?

Dogs are allowed. The pet fee is USD 29.95 per pet per night. The hotel has no weight limits or breed restrictions. Please notify the hotel directly prior to your arrival date if traveling with a pet. Pet-friendly rooms are limited. All fees mentioned are subject to change without prior notice and applicable taxes.

Is parking available?

The hotel does not have on-site parking. However, there are several nearby garages and metered street parking options. You can use the SpotHero app to locate parking spots easily.

What time is check-in and check-out?

Check-in time starts at 4:00 PM and check-out is until 12:00 PM.

Does the property have WiFi?

Yes, free WiFi access is available.

Does the property have a restaurant?

Yes. Guests can dine at Trophy Room and Quick Bites & Bevvies.

Does the property serve a complimentary breakfast?

No. However, guests can purchase breakfast at the on-site restaurant.

Does the hotel have a pool?

This hotel does not have an on-site pool.

Does the property offers a shuttle service?

No, this property does not offer an airport or area shuttle.

Is there a resort fee?

A daily amenity fee of USD 24.95 + tax will be collected upon arrival. This fee includes the following: - In-room bottled water - In-room coffee - Internet access - Sporting facilities or equipment *All fees mentioned are subject to change without prior notice and applicable taxes.

Are there any additional charges besides room and tax?

The following fees apply: - A 1.5% fee for Boston-Cambridge Tourism Destination Marketing District Assessment and a 2.75% fee for Convention Center Fee are added to your booking. - A $50.00 fee for incidental charges will be debited to your card for each day of the planned stay. *All fees mentioned are subject to change without prior notice and applicable taxes.

Can I reserve a smoking room?

No. This property is 100% smoke-free. A fee of up to USD 500 will be assessed for smoking in a non-smoking room.

Is the hotel accessible? What accessible amenities are available?

The hotel has limited accessibility. Please contact the hotel directly for specific accessible needs to ensure the hotel will be able to meet your requirements.

What are the attractions nearby?

Below are the top attractions near Staypineapple, A Delightful Hotel, South End Boston, and their approximate distances: Back Bay 0.7 miles The View Boston Observatory 1.3 miles Boston Tea Party Ship & Museum 1.4 miles Boston Museum of Fine Arts 1.7 miles Old State House 1.7 miles Custom House Tower 1.8 miles TD Grden 1.9 miles Central Square 3.9 miles JFK Presidential Library & Museum 4.1 miles Inman Square 4.8 miles LEGO Discovery Center Boston 5.2 miles Fenway Park 6.3 miles Boston Public Garden 9.4 miles Boston Common 9.5 miles

How far is the nearest airport from Staypineapple, A Delightful Hotel, South End Boston?

The nearest airport is Boston Logan International Airport, about 4.1 miles from the property.

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