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Staypineapple, A Delightful Hotel, South End

3.0 star property
This charming South End boutique hotel blends warm hospitality with vibrant city energy, creating a perfect base for exploring Boston's historic neighborhoods

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Photo gallery for Staypineapple, A Delightful Hotel, South End

A brick building with a green door and a covered outdoor seating area. - Staypineapple, A Delightful Hotel, South End (Boston)
A restaurant interior with a bar area, green chairs, a patterned floor, and large windows. - Staypineapple, A Delightful Hotel, South End (Boston)
A restaurant with a checkered floor, green upholstered seating, and a bar area. - Staypineapple, A Delightful Hotel, South End (Boston)
A lobby with a checkered marble floor, a reception desk, and two bicycles. - Staypineapple, A Delightful Hotel, South End (Boston)
A lobby with a checkered floor, a green fireplace, and modern seating. - Staypineapple, A Delightful Hotel, South End (Boston)
Staypineapple, A Delightful Hotel in South End offers a relaxing spot after exploring Boston. Enjoy the on-site bar and restaurant, free bike rentals to visit Copley Place and Newbury Street, and multilingual staff for local insights and authentic experiences.

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)
  • 18 sq m
  • 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)
  • 18 sq m
  • Sleeps 2
  • 1 King Bed

DOUBLE BAY VIEW KING BED

  • Sleeps 4

DOUBLE CITY VIEW KING BED

  • Sleeps 4

DOUBLE DELUXE KING BED

  • Sleeps 4

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. Visit our Boston travel guide
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 cityscape with a prominent skyscraper, various buildings, and a distant body of water.
    Copley Place
    8 min walk - 0.5 miles
  • A park with manicured hedges, flowering plants, and a city skyline in the background.
    Boston Common
    10 min walk - 0.5 miles
  • A marathon with runners on a city street lined with buildings and flags.
    Boston Marathon Finish Line
    10 min walk - 0.6 miles

Getting around

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

Restaurants

  • The Friendly Toast
    4 min walk
  • Grill 23 & Bar
    4 min walk
  • Flour Bakery + Cafe
    5 min walk
  • Club Café
    3 min walk
  • The Banks Seafood and Steak
    6 min walk

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Property amenities

Internet

  • Available in all rooms: Free internet

Parking and transportation

  • No onsite parking available

Food and drink

  • A bar/lounge
  • A restaurant
  • Coffee and tea in common areas

Restaurants on site

  • Trophy Room

Things to do

  • Free bicycle rentals

Conveniences

  • 24-hour front desk
  • Luggage storage
  • Water dispenser

Guest services

  • Concierge services
  • Housekeeping (on request)
  • Multilingual staff
  • Tour and ticket assistance

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Elevator
  • Hardwood flooring in room
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk
  • Wheelchair-accessible restaurant

More

  • 1 building
  • 8 floors
  • Built in 1900
  • Fireplace in lobby
  • No plastic water bottles
  • Smoking not allowed
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Down comforter
  • Hypo-allergenic bedding
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 50-inch flat-screen TV with cable/satellite channels
  • iPod dock
  • Streaming services

Food and drink

  • Coffee/tea maker
  • Free bottled water

More

  • Air conditioning (climate-controlled)
  • Desk
  • Free local calls
  • Heating (climate-controlled)
  • Iron/ironing board on request
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4 PM; Check-in end time: midnight
Minimum check-in age: 18

Check-out

Check-out before noon
Contactless check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 29.95 per pet, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Specific rooms only, restrictions apply; pet-friendly rooms can be requested by contacting the property at the number on the booking confirmation
Food and water bowls are available

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 29.06 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • In-room bottled water
  • In-room coffee
  • Internet access
  • Sporting facilities or equipment

We have included all charges provided to us by the property.

Optional extras

  • Pet fee: USD 29.95 per pet, per night
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Tax ID - C0014880350
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a smoke detector
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property

We should mention

This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

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 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

8.4

Location

9.4

Staff & service

8.8

Property conditions & facilities
Rating 10 - Excellent. 662 out of 1010 reviews
Rating 8 - Good. 220 out of 1010 reviews
Rating 6 - Okay. 70 out of 1010 reviews
Rating 4 - Poor. 32 out of 1010 reviews
Rating 2 - Terrible. 26 out of 1010 reviews

Reviews

Verified

8/10 Good

Paul

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

8/10 Good

Tatiana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Jul 2026
Verified

10/10 Excellent

Shannon

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

10/10 Excellent

Karina

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

8/10 Good

robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great value for the price. Bathroom is a little small, but able to navigate my way around it. Staff was helpful and kind. The internet was a little glitchy. Close to Fenway and other popular landmarks in Boston. I would stay here again.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
In the center of Back Bay. Everything was within walking distance. Bar had all the concoctions and food. Friendly staff. Would stay there again.
Stayed 2 nights in May 2026
Verified

10/10 Excellent

Althea

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

10/10 Excellent

Tatania

Liked: Cleanliness, staff & service, property conditions & facilities
Close to public transit and several walkable restaurants
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Laura

Liked: Cleanliness
Accommodations and staff were above what I expected. Will absolutely be back.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

margaret

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
For such a small room all storage questions answered with good design. The coffee maker was a bit funky but worked perfectly.
Stayed 2 nights in May 2026
Verified

8/10 Good

Yuko

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great downtown location and affordable rates for budget travelers. The staff was great. The room (expesicially the barhtoom) was teeny-tiny.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Simeng

Liked: Cleanliness, property conditions & facilities
the staff is excellent!
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Hortencia

Liked: Cleanliness, staff & service, amenities
Clean and great location. Wonderful service. Really enjoyed our stay and will return.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Aimee

Liked: Cleanliness, amenities, property conditions & facilities
Super cute room staff was great
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities
The cleanliness of the entire property was above average, the friendliness was fantastic
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
So fun!! Smaller boutique feel. But the staff was amazing. The theme was super cute. The restaurant was yummy. All good.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Skyler

Liked: Cleanliness, amenities, property conditions & facilities
Everyone was very kind and accommodating! Rooms were so cozy and clean. Would definitely stay again.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Jasmyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs!
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Jan S

Liked: Cleanliness, amenities, property conditions & facilities
We've been to several Staypineapple hotels and they're always great. Clean rooms with comfortable beds and nice little extras that make the stay more pleasant.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

waileong

Liked: Cleanliness, staff & service, amenities
staff and room are great
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and comfortable room. Smaller, but comfortable. Bed was very cozy and loved the robes. Good location we walked everywhere. Quite noisy at night from traffic outside. But would definitely stay again.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Dandre

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was absolutely amazing and met all needs.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Joy

Liked: Cleanliness, amenities, property conditions & facilities
Loved this hotel. Convenient to everything, nice staff , rooms had everything you could need and the bed was very cozy. Loved the free reusable water bottle and the complimentary cocktail at the bar . Highly recommend
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean. Friendly and helpful staffs. Free water bottle.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

William

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was clean, the staff was friendly and helpful, the bed was comfortable, and the location was within walking distance to many attractions. The only minor complaint I have is that the shower isn't great if you're over 6 feet tall.
Stayed 2 nights in Mar 2026