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Staypineapple, A Delightful Hotel, South End

3.0 star property
3-star boutique hotel near Copley Square

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Bar (on property)
Lobby sitting area
Reception
Premium bedding, down comforters, pillowtop beds, desk

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pet friendly
  • 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, Copley Place
    ‪6 min walk‬
  • Place, Boston Common
    ‪10 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪4 min drive‬

Room options

View all photos for South End Corner King

Premium bedding, down comforters, pillowtop beds, desk

South End Corner King

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

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.0 out of 10
Wonderful
(47 reviews)
  • Sleeps 2
  • 1 King Bed

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About the area

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 - 0.6 km
  • Copley Place - 6 min walk - 0.6 km
  • Newbury Street - 8 min walk - 0.7 km
  • Boston Common - 10 min walk - 0.8 km
  • Boston Marathon Finish Line - 10 min walk - 0.9 km

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
  • ‪Club Café - ‬4 min walk
  • ‪Grill 23 & Bar - ‬4 min walk
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪The Banks Seafood and Steak - ‬6 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
  • 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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includes taxes & fees
Apr 5 - Apr 6
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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

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
  • Shower
  • 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
  • Sporting facilities or equipment

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 Mar 30, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Apr 5, 2026 start from CA $151, excluding 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 8.1 mi (23-min drive) from Revere Beach.

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. 644 out of 1006 reviews
Rating 8 - Good. 237 out of 1006 reviews
Rating 6 - Okay. 70 out of 1006 reviews
Rating 4 - Poor. 31 out of 1006 reviews
Rating 2 - Terrible. 24 out of 1006 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

Reviews

10/10 Excellent

Adam

Stayed 2 nights in Dec 2025

8/10 Good

Chelsea

Stayed 2 nights in Dec 2025

10/10 Excellent

Thomas

Stayed 1 night in Dec 2025

10/10 Excellent

John, Salem

Liked: Cleanliness, property conditions & facilities
Small but well layed out room. Small bathroom but very functional. Room was up to sate and very clean. Staff very friendly and helpful. Nice bar area.
Bathroom
No closet but very creative storage.
Wall mounted wide screen
All rooms have Keurig coffee makers.
Stayed 2 nights in Dec 2025

10/10 Excellent

Chris

Stayed 1 night in Dec 2025

10/10 Excellent

Griffin

Stayed 1 night in Dec 2025

10/10 Excellent

Nicholas

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Dec 2025

10/10 Excellent

Edward

Stayed 1 night in Dec 2025

10/10 Excellent

Yimo

Stayed 2 nights in Dec 2025

10/10 Excellent

Kevin

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
In an extremely cute area - a short walk and you're in this beautiful neighborhood with great shops and food. The hotel staff were so incredibly nice. The room was very comfortable. The bathroom is a little small, but very clean and has a great shower. Would absolutely stay here again!
Stayed 4 nights in Jun 2025

10/10 Excellent

Russell

Stayed 2 nights in Nov 2025

8/10 Good

Efrain

Stayed 1 night in Nov 2025

10/10 Excellent

James

Business traveller
Liked: Cleanliness, staff & service, amenities
Location
Stayed 4 nights in Nov 2025

6/10 Okay

Eleni

Travelled with partner
Liked: Cleanliness, staff & service
The staff were friendly, the location was conveniently located making it easy to walk around the city and overall the rooms were very clean and comfortable. We enjoyed the bedding and aesthetic of the rooms. The hotel is in a very old building and there were a few things that could have been fixed. The water knob was loose and kept falling during a shower, leaving us showering with extremely hot water. There was a hole in the wall where the electrical box was (the cover was taken off and never replaced). The walls are extremely thin. After 10pm you could hear every little thing the neighbours were saying and 2 of our 4 nights were could barely sleep due to the sounds of music, tv, and screaming from adjacent rooms. For the price we paid we would have expected a higher quality room, especially since there is a “resort fee” cost for basic things like water and wifi that we would have rather opt out of.
Stayed 4 nights in Nov 2025

10/10 Excellent

Kenneth

Travelled with group
Liked: Cleanliness, staff & service, amenities
Staff were great and helpful. Room was clean. The umbrella came in big as I forgot to bring one for the one rainy day.
Stayed 3 nights in Nov 2025

10/10 Excellent

Philip

Travelled with family
Liked: Cleanliness, staff & service, amenities
Great location. Check-in staff was exceptional. Nice room.
Stayed 2 nights in Nov 2025

8/10 Good

Heather

Stayed 1 night in Nov 2025

10/10 Excellent

Maija

Travelled with family
Liked: Cleanliness, staff & service, amenities
the room was very clean. bathroom is very small but shower was great and the towels were oversized, a big plus. bed was very comfy and came with 2 separate blankets which was amazing. the staff was friendly and helpful. i would definitely return
Stayed 1 night in Nov 2025

10/10 Excellent

Lauren

Liked: Cleanliness, amenities, property conditions & facilities
Room was lovely. Clean and well maintained. The front desk stay were very friendly and helpful. I will definitely stay there again !
Stayed 5 nights in Nov 2025

10/10 Excellent

Tymea

Liked: Cleanliness
Stayed 2 nights in Nov 2025

10/10 Excellent

Rachel

Stayed 1 night in Nov 2025

10/10 Excellent

Dena

Liked: Cleanliness, staff & service, property conditions & facilities
Cute set up and fun vibe
Stayed 1 night in Nov 2025

8/10 Good

Rod

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Really cute hotel and good restaurant. On a cool Boston night room was warm and comforting. Enjoyed our visit Would go back again.
Stayed 1 night in Nov 2025

10/10 Excellent

Yamel

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Staff courteous. Very pretty room!
Stayed 1 night in Nov 2025

6/10 Okay

Jill

Travelled with family
Liked: Cleanliness
Disliked: Amenities
Most of the staff was great, especially Cynthia! It would be great if there was food available more than between the hours of 4-11. The bar staff could also be a bit kinder to women who are staying in the hotel. Everyone was great with my dog but the communication was pretty poor. I was told that I was booked through Thursday night by one person and then had to scramble for somewhere to stay on my last night in town with less than an hour notice. The person who told me this wasn’t very kind and i got locked out of my room while my dog was in there. There was no one at the desk and it was all very stressful. Overall, it was okay but I would stay somewhere else next time.
Stayed 5 nights in Nov 2025