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

26 Chandler Street • Boston, MA 02116
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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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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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427eugeniab
"So Comfy and Unforgettable!!"
TripAdvisor user rating 5.0 out of 5
Reviewed October 23, 2025 NEW
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!
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chrin22
Plano, Texas
"Fun hotel at good location."
TripAdvisor user rating 5.0 out of 5
Reviewed October 21, 2025 NEW
Overall it was a very good hotel stay at a reasonable price compared to other hotels in the area. It was within easy walking distance of Boston Commons, We enjoyed the ability to check out bicycles to go see local sights, and on the one day we walked to Beacon Hill there was a good steady rain, so the ability to check out umbrellas was very helpful. When our departing flight was delayed the front desk was able to accommodate a late checkout. The Saturday night traffic noise was a medium volume, but it died down before it got too late and we didn't notice any real traffic noise on Sunday morning or even on weekday mornings. We got a corner room and it was pretty small, but I assume that is normal for an urban Boston hotel. My only complaint is that the lobby coffee was only available at certain times (until 8:00 AM on Sunday morning), and the maid didn't refill the coffee pods in our room. The only option to get coffee was to pay for it in the attached bar/restaurant, which seemed like an unnecessary add-on charge.
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1985smn
Ontario, California
"Stay With the Pineapple"
TripAdvisor user rating 5.0 out of 5
Reviewed October 20, 2025 NEW
Staypineapple was a really cute, boutique style hotel. I spent six days here and enjoyed my time! It was partly solo and then my cousin joined later on. We each had our own room next door to each other. I really appreciated the staff making accommodations for my cousin to have a room next door considering we checked in days apart. I enjoyed having a reusable water bottle and then access to water 24/7 in the lobby. I tried the pineapple teriyaki wings and they were really good. The rooms are super small, BUT you know that when you look up the hotel. It’s perfect for solo travelers but I don’t know couples or friends would enjoy the space. The shower has a half door. I don’t like when hotels just don’t give a full door to a shower or curtains. But it wasn’t a big deal to mark them down. It is within walking distance (5-20 minutes) of food places and things to do. The Back Bay Orange line is also about a 5 minute walk. Logan airport is about an 11 minute Lyft ride or so without traffic. Staff was friendly. I felt safe in the area it’s located in. I would definitely stay here again.
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mackielacey
Ormond Beach, Florida
"Can Not Wait To Go Back!"
TripAdvisor user rating 5.0 out of 5
Reviewed October 02, 2025 NEW
What a fantastic hotel! The location is great, walked to Boston Common, the North End, etc. Lauren at the front desk was so welcoming, helpful, went above and beyond. The bar area on site and bartenders were wonderful. The food there was also delicious. The pizza and blt were spot on. My room was so eclectic and fun! Loved the bed, so comfy. Nice shower, great water pressure. The pineapple cookies and welcome adult beverage was most appreciated. Can not wait to go back!!!!!
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Roving07285006136
"Comfy hotel centrally located"
TripAdvisor user rating 5.0 out of 5
Reviewed September 24, 2025
Friendly staff Mitchell and Cynthia nothing we asked them was too much trouble and were always willing to help. Clean room with a super comfy bed
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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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