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Staypineapple, A Delightful Hotel, South End

Property class: 3
3-star boutique hotel near Copley Square

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

A brick building with a green door and a covered outdoor seating area.
A lobby with a checkered floor, a green fireplace, and modern seating.
A restaurant interior with a bar area, green chairs, a patterned floor, and large windows.
A lobby with a checkered marble floor, a reception desk, and two bicycles.
A restaurant with a checkered floor, green upholstered seating, and a bar area.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Square
    ‪6 min walk‬
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Boston Common
    ‪10 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪6 min drive‬

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

DOUBLE BAY VIEW KING BED

  • Sleeps 4

DOUBLE CITY VIEW KING BED

  • Sleeps 4

DOUBLE DELUXE KING BED

  • Sleeps 4

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About the neighborhood

Boston

Heart of Boston.Within a 10-minute walk of this South End hotel, you'll find Copley Square and Boston Common. Boston University and Fenway Park are also within 2 miles (3 km).

What's nearby

  • Copley Square - 6 min walk - 0.4 miles
  • Newbury Street - 8 min walk - 0.5 miles
  • Copley Place - 8 min walk - 0.5 miles
  • Boston Common - 10 min walk - 0.5 miles
  • Boston Marathon Finish Line - 10 min walk - 0.6 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

  • ‪Dunkin' - ‬6 min walk
  • The Salty Pig
  • ‪Grill 23 & Bar - ‬4 min walk
  • ‪Club Café - ‬3 min walk
  • ‪Flour Bakery + Cafe - ‬5 min walk

About this property

Staypineapple, A Delightful Hotel, South End

3-star boutique hotel near Copley Square
There's a restaurant on site. You can enjoy a drink at the bar/lounge. Multilingual staff, tour/ticket assistance, and coffee/tea in a common area are also featured at the business-friendly Staypineapple, A Delightful Hotel, South End.

This 3-star Boston hotel is smoke free.

  • 1 building
  • 56 guestrooms or units
  • 8 levels
  • Built in 1900
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff is multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Fireplace in lobby
  • Elevator
  • No smoking on site
  • Water dispenser
  • Bar or lounge
  • Dining venue
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with complimentary bottled water and coffee/tea makers. Pillowtop beds feature down comforters and premium bedding. 50-inch flat-screen televisions come with satellite channels.

Bathrooms include showers, bathrobes, designer toiletries, and complimentary toiletries. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided on request.

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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

Things to do

  • Free bicycle rentals

Accessibility

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

Room amenities

Entertainment

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

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

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: USD 29.95 per pet, per night
  • Only dogs are allowed
  • Maximum 2 pets
  • Food and water bowls are available
  • Certain rooms only, restrictions apply
  • You can request a pet-friendly room by reaching out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

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

Guests will be asked to pay the following charges at the property:

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

We've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

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

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. No onsite parking is available. The tax ID number is C0014880350. This property accepts Visa, Mastercard, American Express, Discover, Diners Club, and Union Pay. Cash is not accepted. For guests' safety, the property includes a smoke detector in each accommodation. Cashless payment methods are available for all transactions.

We should mention

  • Pets are welcome in certain rooms only; other restrictions apply (please see the Fees section for related charges). To make arrangements for your pet, contact the property directly at the number on your booking confirmation.
  • This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).

Property is also known as

Chandler Inn Hotel Boston
Chandler Boston
Staypineapple A Delightful Hotel South End
"Staypineapple A Delightful Hotel South End"
Staypineapple, A Delightful Hotel, South End Hotel
Staypineapple, A Delightful Hotel, South End Boston
Staypineapple, A Delightful Hotel, South End Hotel Boston

Frequently asked questions

How close is Staypineapple, A Delightful Hotel, South End to the airport?

Staypineapple, A Delightful Hotel, South End is 4.8 mi (16-min drive) away from the Boston, MA (BNH-Boston Harbor Seaplane Base) airport, the closest popular airport to the property.

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

As of Aug 14, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Aug 30, 2026 start from $172, 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.

Does Staypineapple, A Delightful Hotel, South End have an airport shuttle?

Airport shuttle services are not available at Staypineapple, A Delightful Hotel, South End.

How close is Staypineapple, A Delightful Hotel, South End to the beach?

This hotel is a short 8-minute walk from Carson Beach and 8.1 mi (23-min drive) from Revere Beach. Don't forget your sunscreen!

Does Staypineapple, A Delightful Hotel, South End offer free breakfast?

Staypineapple, A Delightful Hotel, South End does not offer free breakfast.

Is there a casino at Staypineapple, A Delightful Hotel, South End?

No, there is no casino at this hotel, but Encore Boston Harbor (9-min drive) is nearby.

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

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

Is there free parking at Staypineapple, A Delightful Hotel, South End?

Free parking is not available at this hotel.

Does Staypineapple, A Delightful Hotel, South End have a pool?

Staypineapple, A Delightful Hotel, South End does not have a pool.

Does Staypineapple, A Delightful Hotel, South End have a restaurant?

Staypineapple, A Delightful Hotel, South End is home to Trophy Room, which features American cuisine and brunch.

Does Staypineapple, A Delightful Hotel, South End have a spa?

There are no spa services available at this hotel.

How close is Staypineapple, A Delightful Hotel, South End to downtown Boston?

Staypineapple, A Delightful Hotel, South End is 1 mi away from Boston.

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 660 out of 1000 reviews
Rating 8 - Good. 218 out of 1000 reviews
Rating 6 - Okay. 67 out of 1000 reviews
Rating 4 - Poor. 30 out of 1000 reviews
Rating 2 - Terrible. 25 out of 1000 reviews

9.4/10

Cleanliness

9.4/10

Staff & service

8.6/10

Amenities

8.8/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay in Boston. Convenient location, comfortable rooms.
Stayed 3 nights in Apr 2026
Verified review

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 review

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 review

8/10 Good

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Conveniently located in walking distance to Amtrak and metro stations, the theatre district, and the start of the Freedom Trail, lovely cafes and restaurants as well.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

John

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The rooms were clean and functional Location was convenient, about 6 minute walk to Backbay subway station, fifth stop is State st tourist area Recommend Berkleyperks cafe for breakfast
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Johannah

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely friendly great bar so many PINEAPPLES :)
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Rajarshi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room and good amenities includd with room.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Althea

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

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 review

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
nice hotel near back bay station
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely rooms, charming space, convenient to attractions.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Fernando

Wonderful stay
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Yanira

Liked: Cleanliness, staff & service
Disliked: Amenities
Beautiful rooms
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Manuel

Liked: Cleanliness, staff & service, property conditions & facilities
clean and comfortable
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Charles

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Hotel is clean. Staff is friendly and it has a restaurant/bar. Building is old and room was small, but everything has been updated. Overall good experience.
Stayed 3 nights in May 2026
Verified review

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 review

8/10 Good

Tomiko

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The hotel staff was friendly and professional. The hotel is located near the Back Bay train station, restaurants, and convenience stores. The room I stayed in is laid out in an efficient manner and styled in a friendly manner. The amenities in the room were perfect.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Neil

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Thoroughly enjoyed my stay here. Excellent value.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Sean

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
small but well appointed room. great for shorter stays. Not a lot of extra space. Bed and pillows were comfy. I would go back. location was very convenient.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Janell

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband & I had a great vacation stay here. The bedding, pillows, coffee machine & Tommy Bahama products were a nice touch. Every employee we encountered was kind, courteous & friendly. A special shout out to Gabe, he was outstanding and went above and beyond our expectations with his kindness! This location is great for walking & we always felt very safe. We also LOVED the still water station near the front desk and used it the entire time during our stay!!!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Jill

Liked: Cleanliness, staff & service, property conditions & facilities
The room was clean and with cute decor.
Stayed 1 night in Mar 2026
Verified review

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 review

10/10 Excellent

Jean

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely boutique hotel with a cozy vibe and updated amenitities. Location was perfect in the Back Bay / South End area of Boston. Close to many restaurants, concert halls, and shopping. Cobblestone streets in the area and an nice bar and cafe next store with a discount on drinks at the bar. Amenities were plenty and the rooms were decorated in modern fun vibe. Rooms were on the smaller side but amenties were plentiful and very efficient as well as comfortable. Highly recommend for a boutique hotel with amenities in a great area.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Megan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The best!
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Edgar

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I had a great experience staying at Staypineapple in the South End. The hotel has a really fun, unique vibe while still feeling clean and well put together. The rooms were cozy but thoughtfully designed, and the bed was honestly one of the most comfortable I’ve slept in. The staff was friendly and welcoming, and the location made it easy to get around Boston and explore nearby restaurants and shops. Small touches like the complimentary coffee and overall atmosphere made the stay feel a little more special. Would definitely stay here again and recommend it to anyone looking for something a bit different from a typical hotel.
Stayed 2 nights in Apr 2026