Staypineapple, A Delightful Hotel, South End

Property class: 3

Choose dates to view prices

Located close to Copley Square and Boston Common, Staypineapple, A Delightful Hotel, South End provides a fireplace in the lobby, a bar, and a restaurant.
VIP Access

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk

Room options

View all photos for South End Corner King

A neatly arranged hotel room with a bed, a television, a small table, and a yellow suitcase.

South End Corner King

8.8 out of 10
Excellent
(9 reviews)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

A hotel room with a bed, a nightstand, a lamp, a suitcase, and a window with a view.

Back Bay King

9.2 out of 10
Wonderful
(52 reviews)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

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Total with taxes and fees
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About the neighborhood

Located in South End, a neighborhood in Boston, Staypineapple, A Delightful Hotel, South End is near the airport and near a metro station. Faneuil Hall Marketplace and Fenway Park are notable landmarks, and the area's natural beauty can be seen at Boston Common and Boston Harbor. Looking to enjoy an event or a game? See what's going on at TD Garden, or consider Encore Boston Harbor for a night out.
Map
26 Chandler St, Boston, MA, 02116

What's nearby

  • A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.
    Copley Square
    6 min walk - 0.4 miles
  • A sidewalk lined with brick buildings, outdoor cafes, and pedestrians.
    Newbury Street
    8 min walk - 0.5 miles
  • A row of bronze sculptures of birds with colorful decorations on a cobblestone path in a park.
    Boston Public Garden
    8 min walk - 0.5 miles
  • A city skyline at dusk with illuminated buildings, a river, and a bridge.
    Copley Place
    8 min walk - 0.5 miles
  • A public park with a large fountain, surrounded by trees and modern buildings.
    Boston Common
    10 min walk - 0.5 miles

Getting around

  • Back Bay Station
    5 min walk
  • Arlington Station
    8 min walk
  • Boston, MA (BNH-Boston Harbor Seaplane Base)
    16 min drive

Restaurants

  • The Friendly Toast
    4 min walk
  • Club Café
    3 min walk
  • Grill 23 & Bar
    4 min walk
  • Flour Bakery + Cafe
    5 min walk
  • Barcelona Wine Bar
    4 min walk

About this property

Staypineapple, A Delightful Hotel, South End

  • Boutique hotel near Copley Square
  • Located close to Boston Common and Fenway Park, Staypineapple, A Delightful Hotel, South End provides a fireplace in the lobby, a bar, and a restaurant.
  • You'll also find perks like:
    • Free bicycle rentals, coffee/tea in the lobby, and tour/ticket assistance
    • Smoke-free premises, concierge services, and a 24-hour front desk
    • Multilingual staff, luggage storage, and a water dispenser
    • Guest reviews give top marks for the helpful staff and location
  • Room features
  • All 56 rooms offer comforts such as premium bedding and laptop-friendly workspaces, in addition to thoughtful touches like air conditioning and bathrobes. Guest reviews speak positively of the clean rooms at the property.
  • Extra amenities include:
    • Hypo-allergenic bedding, pillowtop mattresses, and down comforters
    • Bathrooms with designer toiletries and showers
    • 50-inch flat-screen TVs with streaming services and cable channels
    • Coffee/tea makers, heating, and housekeeping

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A spacious lobby with a fireplace, bookshelves, and a checkered floor.
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  • Pet friendly
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  • Air conditioning
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$109 nightly
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Nov 23 - Nov 24
Total with taxes and fees
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Frequently asked questions

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

Yes, this property allows dogs (limit 2 total). There's a fee of USD 29.95 per pet, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Staypineapple, A Delightful Hotel, South End?

As of Nov 10, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Nov 24, 2026 start from $134, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

This property doesn't offer parking.

What time is check-in at Staypineapple, A Delightful Hotel, South End?

Check-in start time: 4 PM; Check-in end time: midnight.

What time is check-out at Staypineapple, A Delightful Hotel, South End?

Check-out is at noon.

Where is Staypineapple, A Delightful Hotel, South End located?

Located in South End, this boutique hotel is within a 10-minute walk of Copley Square and Boston Common. Boston University and Fenway Park are also within 2 mi (3 km). Arlington Station is 8 minutes by foot and Tufts Medical Center Station is 9 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Staypineapple, A Delightful Hotel, South End Reviews

9.0

Wonderful

9.4

Cleanliness

8.0

Location

9.4

Staff & service

9.0

Property conditions & facilities
Rating 10 - Excellent. 674 out of 1007 reviews
Rating 8 - Good. 208 out of 1007 reviews
Rating 6 - Okay. 72 out of 1007 reviews
Rating 4 - Poor. 31 out of 1007 reviews
Rating 2 - Terrible. 22 out of 1007 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exceptional staff, cute design, great location!
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I liked the decor, the attentiveness of the staff, the special goose down comforter and duve, and also the old world feel. Also there are many restaurants near the hotel including Legal Seafood
Stayed 1 night in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the Stay Pineapple! Very clean; friendly staff and love the properties dog!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a cute place close to everything in Boston! Super clean and well maintained. Due to the room size I would recommend it for solo travelers or couples only. The bedding was divine and I loved that each person had their own duvet. We would definitely stay here again.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small rooms but efficient. Comfy beds. Great location. Very helpful staff. Would def stay again.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A very clean boutique hotel. Bed was very comfortable. Will definitely stay again when we go back to Boston
Stayed 2 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Kind of a funky hotel on the outside, but once you got in the room it was great!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Pet-friendly but clean. Friendly staff. Convenient location. We enjoyed our stay.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staypineapple was great! Loved the comforters on the bed, they were super comfy. The bathroom was a little small but it was in a great location in the South End. Great weekend for me and my boyfriend, we would definitely go back
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very small but well organized place. Very nice staff
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We LOVED this hotel. It is adorable, in a great area, and the staff members are very sweet. We will definitely be back!
Stayed 1 night in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel with friendly staff from the moment of booking to leaving the hotel. Very comfortable bed and pillows!! Great location too!
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We enjoyed the quirky features of this hotel. The staff were friendly & helpful. There was a problem with the water supply (due to building works next door) & staff kept us updated with the situation.
Stayed 1 night in Aug 2026
Verified review

6/10 Okay

Liked: Cleanliness, property conditions & facilities
The rooms were small. The towels very Scratchy. The restaurant was ok. Food was good, staff only ok.
Stayed 2 nights in Aug 2026
Verified review

6/10 Okay

Liked: Staff & service
Okay stay. Room was not that well kept. Noisy Split AC. Cramped space.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great boutique hotel in a great location. You can walk to most tourist attractions.
Stayed 3 nights in Jun 2026
Verified review

6/10 Okay

Liked: Staff & service, amenities
The staff were very friendly and the room was nice and cozy. However the faucet in the bathroom was partially broken and the shower head pressure wasn’t great. Overall it was an good experience
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The most comfortable bed. Clean room.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Great location, very clean and staff were awesome
Stayed 6 nights in Apr 2026
Verified review

2/10 Terrible

Review was terrible because I booked it for my son for work trip! His flight got cancelled so he drove 5 hours the next day (for work) to get to hotel to find out his room was given away with no notice. Not great customer service
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good location, great staff, clean rooms
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
There’s no airport shuttle, but the hotel is clean. The staff is helpful and location cannot be beat!
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Great shopping and restaurant nearby
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in Jul 2026