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Staypineapple, A Delightful Hotel, South End

★★★★ 26 Chandler Street, Boston, US

8.5 guest rating· 1624 reviews

Travelling with a dog

Dogs are welcome at Staypineapple, A Delightful Hotel, South End; it lists pets-allowed in its own facility data.

On top of the basics it offers Pet bowls and Pet basket.

About this hotel

Charming European-Style Boutique Hotel in Boston's South End

Modern Amenities : Each room at Staypineapple, South End boasts a flat-screen TV, iPod docking station, and a luxurious walk-in marble shower in the private bathroom.

Convenient Services : Guests can enjoy free WiFi, a work desk, and a direct line to the 24-hour front desk for any needs that may arise during their stay.

Prime Location : Situated in the historic South End, the hotel is just a short stroll away from renowned restaurants and attractions, including the vibrant Back Bay area and upscale shops on Newbury Street.

Ready to experience the perfect blend of comfort and sophistication? Book your stay at Staypineapple, South End now!

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Rooms & rates

Back Bay King

Sleeps 2 · 18 m² · Extra-large double bed (Super-king size)

  • Coffee/tea maker
  • Coffee machine
  • Shower
  • TV
  • Hair dryer

South End Corner King

Sleeps 2 · 18 m² · Extra-large double bed (Super-king size)

  • Coffee/tea maker
  • Coffee machine
  • Shower
  • Hair dryer
  • Bottle of water

Amenities

  • Free WiFi
  • Restaurant
  • Bar
  • Air conditioning
  • Pets allowed
  • Pet basket
  • Pet bowls
  • 24-hour front desk
  • Non-smoking rooms
  • Non-smoking throughout
  • Cashless payment available
  • Cleaning standards that are effective against Coronavirus
  • Concierge service
  • Daily housekeeping
Show all 29 amenities
  • Face masks for guests available
  • Fire extinguishers
  • First aid kit available
  • Guest rooms disinfected between stays
  • Guests can opt-out any cleaning services during stay
  • Hand sanitizer in guest room and key areas
  • Heating
  • Invoice provided
  • Key card access
  • Laundry washed per local authority guidelines
  • Lift / Elevator
  • Luggage storage
  • Sanitized tableware & silverware
  • Smoke alarms
  • Staff adhere to local safety protocols

Location

What guests say8.51624 reviews

+ Friendly staff+ Clean rooms+ Great location+ Fun amenitiesNoise issuesSmall room sizesLimited storage space
Cleanliness8.1
Service9.1
Location8.7
Room Quality7.6
Amenities8.6
Value for Money9.1

A nice place to stay

9.0

The staff is very helpful. And welcoming. Location is. Good. Overall a very nice experience.

The sidewalks. In the area. Are interesting. They are red brick very old fashioned. But not very comfortable to walk on.

eric · US · 2026-08-21

Guest review

8.0

Le personnel est très gentil et assez réactif quand vous rencontrez un problème. L’hôtel est si bien placé qu’il est possible de visiter une grande partie de Boston à pied.

La chambre n’était malheureusement pas propre, bien que le nécessaire ait été fait, il y avait des cheveux sur les draps, sur le sol et dans la douche ce qui n’est pas propre à mon sens. Il faudrait accentuer le nettoyage notamment en passant l’aspirateur.

Samanta · FR · 2026-08-21

Guest review

4.0

The nice extras in the room. Pineapple engraved, nice towels, bedding.

The entrance, front desk area, was unclean, messy, and very odd. The first impression was like walking into a 1 or 2 star old motel. The elevators and walls of the hallways were dirty with a lot of wear. The staff were not cordial!

Keith · US · 2026-08-14

Easy, convenient, served its purpose - but have to say the staff was awesome!

8.0

Location was great and check in was easy

It’s cute in decor but slightly run down 1 just slightly. It is an older building that has been painted to look clean.

Jason · US · 2026-08-14

PawFriendly Stays · questions

Does Staypineapple, A Delightful Hotel, South End allow dogs?
Yes, Staypineapple, A Delightful Hotel, South End is flagged pet-friendly in its listing. Fees and size limits are set by the hotel; ask at booking if they aren't shown.

Good to know

Please note, guest must be a minimum of 18 years of age to check in.

Please note that, Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly. Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

A deposit may be required at the property.