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Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
Staypineapple, A Delightful Hotel, South End – Boston, MA
Staypineapple, A Delightful Hotel, South End – Boston, MA
Check in 4:00 PM
Check out 12:00 PM

About Staypineapple, A Delightful Hotel, South End

Located in Boston's historic South End, this European-style boutique hotel offers modern guest rooms with free WiFi. Staypineapple, South End is within walking distance to many popular restaurants and attractions. Every room at The Staypineapple, South End features a flat-screen TV and iPod docking station. The private bathroom includes a walk-in marble shower. A work desk and telephone with access to the 24-hour front desk are provided for guest convenience. Only steps from the completely nonsmoking property are some of the city's most famous sites. The scenic Back Bay area, as well as the unique shops and gourmet restaurants of Newbury Street are within 10 minutes' walk.

Amenities

  • On-site parking
  • 24-hour front desk
  • On-site dining
  • Bar / lounge
  • Café / coffee shop
  • Express check-in / check-out
  • Concierge
  • Luggage storage
  • Multilingual staff
  • Full kitchen / kitchenette
  • Spa / sauna
  • Pet friendly
  • Wheelchair accessible
  • Public transit access
  • Smoke-free property
  • Air conditioning
  • Elevator
  • In-room safe

Reviews

4.2 / 5
Great 1334 reviews
  • Engine customer Aug 2026

    I loved my stay at Staypineapple and will definitely be my go to when going to Boston. Loved the location, the room, the bed, bedding and the staff. It was all walkable to breakfast, events, shopping, and parking. A+++++

  • Engine customer Aug 2026

    The attention, little details, made our stay special.

  • Engine customer Aug 2026

    The hotel is cute but the rooms look kind of rough. Paint was cracked and chipping, could tell they tried to spot paint sections but the color didnt match the paint already there. I wanted to fall in love with it but my room was directly above the bar so extremely loud until about 1:30 am. Wouldn't have been such an issue but the TV channels didnt work and just had a message that the service was disconnected so I had nothing to help cover the noise. Woke up around 6 am to a dog constantly barking in another room. Amenities were nice, theme is super cute. I was just disappointed in the actual stay & inability to get sleep.

  • Engine customer Aug 2026

    This is such a fun and funky hotel with a great vibe! We loved it.

  • Engine customer Aug 2026

    Cute little hotel near the Theater District.

  • Engine customer Aug 2026

    Mitchell is a super friendly staff member! Check in was quick and easy. Hotel is very cute, room was clean. Room and bathroom were very small. For those staying with a pet, the hotel is very pet friendly. The only things that would have made it more pet friendly is a closer green space for the furry ones to stretch their legs. Would happily stay again and recommend to others.

  • Engine customer Aug 2026

    We discovered this hotel after our daughter moved to Boston and have stayed here at least a half dozen times. It is more affordable than the average downtown hotel but also better than average. Nice amenities, like quality bedding, towels, etc., and lots of special Stay Pineapple touches. The location is great in the walkable and vibrant South End and a short walk to trains. Highly recommend.

  • Engine customer Jul 2026

    A wonderful place, I'm glad we stayed there for my stay in Boston.

  • Engine customer Jul 2026

    The most comfortable bed. Clean room.

  • Engine customer Jul 2026

    We LOVED this hotel. It is adorable, in a great area, and the staff members are very sweet. We will definitely be back!

  • Engine customer Jul 2026

    Our stay at Pineapple was sufficient, but the room and bathroom were extremely small and there is hardly any lobby. I was expecting a little more for the price, to be honest.

  • Engine customer Jul 2026

    Love love this hotel. It was next to anything you can possibly ask for, food, night life, shops, etc. Hotel staff was very helpful with finding parking, once we checked in the got two coasters that you’re able to trade in for a free beverage. They had a little bar downstairs where we got wine. The room was so beautiful and clean. Only down fall is not have a fridge or microwave in the room, otherwise definitely one of the best hotels I’ve stayed in. Will definitely return.

  • Engine customer Jul 2026

    Great location, cute rooms. The bathrooms are incredibly small, almost unmanageable. The building is very old and as a result, the plumbing system piping is very old. We could sewage fumes through the shower drain. It was pervasive through the room and awful. We tried to cover it up with a towel. I’m glad we’re only there one night.

  • Engine customer Jul 2026

    Very pleasant I recommend it.

  • Engine customer Jul 2026

    Rooms and entire property smelled and was wonderfully clean. Staff were friendly. Location was great for us, and we really enjoyed our stay.

  • Engine customer Jul 2026

    Beautifully styled and has one of the kindest, most helpful staff that I’ve ever dealt with. Great experience!

  • Engine customer Jul 2026

    Awesome location reasonable price, very small room but all we needed.

  • Engine customer Jul 2026

    The room was so cute and esthetically pleasing. Was located only. 18 min walk to Back Bay and close by the train. Really enjoyed my stay!

  • Engine customer Jul 2026

    I love this hotel chain and have stayed woth them a few times. Cozy.

  • Engine customer Jul 2026

    The staff was friendly and helpful, but for the money, the room could look nicer.

Frequently asked questions about Staypineapple, A Delightful Hotel, South End

Does Staypineapple, A Delightful Hotel, South End have free Wi-Fi?
Yes, Staypineapple, A Delightful Hotel, South End offers free Wi-Fi for all guests.
Does Staypineapple, A Delightful Hotel, South End offer parking?
Yes, paid self-parking is available on-site at Staypineapple, A Delightful Hotel, South End.
Does Staypineapple, A Delightful Hotel, South End have meeting spaces, conference centers, or conference rooms?
Staypineapple, A Delightful Hotel, South End does not list dedicated meeting or conference facilities. For business event venues in Boston, see business hotels in Boston.
Does Staypineapple, A Delightful Hotel, South End have a fitness center?
Staypineapple, A Delightful Hotel, South End does not list an on-site fitness center. Some properties partner with nearby gyms — check directly with the hotel.
Where is Staypineapple, A Delightful Hotel, South End located, and how walkable is the area?
Staypineapple, A Delightful Hotel, South End is located at 26 Chandler St, Boston, MA 02116. With a Walk Score of 99, the area is rated Walker's Paradise. Most daily errands can be done on foot — ideal for travelers without a car.

What's nearby

Map of points of interest near Staypineapple, A Delightful Hotel, South End
  • Boston Marathon bombings 0.5 mi
  • Boston Marathon 0.6 mi
  • Boston Tea Party 1.0 mi
  • Boston Convention and Exhibition Center 1.2 mi
  • Museum of Fine Arts Boston 1.3 mi
  • Massachusetts Institute of Technology 1.4 mi
  • TD Garden 1.4 mi

Why no public rates?

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