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Staypineapple, A Delightful Hotel, South End

3.0 star property
VIP Access

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Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Bar (on property)
Premium bedding, down duvets, pillow-top beds, desk
Reception
Lobby sitting 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, Copley Place
    ‪6 min walk‬
  • Place, Boston Common
    ‪10 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪4 min drive‬
VIP Access
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  • Extra savings and perks for BONUS+ members
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Room options

View all photos for South End Corner King

Premium bedding, down duvets, pillow-top beds, desk

South End Corner King

8.6 out of 10
Excellent
(8 reviews)
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

Premium bedding, down duvets, pillow-top beds, desk

Back Bay King

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

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Lobby sitting area
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About this property

Staypineapple, A Delightful Hotel, South End

This smoke-free hotel features a restaurant, a bar/lounge and coffee/tea in a common area. Additionally, free use of bicycles, concierge services and a 24-hour front desk are on-site. Housekeeping is available on request.
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with complimentary bottles of water and coffee/tea makers. Pillowtop beds feature down duvets and premium bedding. 50-inch flat-screen televisions come with satellite channels.

Bathrooms include a shower, bathrobes, designer toiletries and complimentary toiletries. Business-friendly amenities include desks and telephones; free local calls are provided (restrictions may apply). Hypo-allergenic bedding and an iron/ironing board can be requested. Housekeeping is provided on request.

Recreational amenities at the hotel include complimentary bicycles.
Our customers tell us that they can't get enough of the helpful staff at Staypineapple, A Delightful Hotel, South End. During your stay, you're just a quick walk from Copley Square. You'll find features such as a restaurant, a bar and concierge services. This property offers pet-friendly amenities, such as food and water bowls.
  • Enjoy American cuisine while dining at Trophy Room
  • Services include a concierge, tour or ticket assistance and luggage storage
  • On-site recreation includes complimentary bicycles
  • Guests have great things to say about the location and the helpful staff
  • Within a 10-minute walk of Copley Square and Boston Common
  • Dogs welcome for a fee (restrictions apply)
  • Pet-friendly amenities are available, including food and water bowls
There's a restaurant on site. You can enjoy a drink at the bar/lounge. Multilingual staff, tour/ticket assistance, and coffee/tea in common area are also featured at the business-friendly Staypineapple, A Delightful Hotel, South End.

This 3-star Boston hotel is smoke free.

Trophy Room – This restaurant specialises in American cuisine and serves brunch and dinner. Guests can enjoy drinks at the bar.

Property amenities

Internet

  • Available in all rooms: Free internet

Parking and transport

  • No on-site 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.
  • Lift
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk

More

  • 1 building
  • 8 floors
  • Built in 1900
  • No plastic water bottles
  • Smoke-free property
  • Water dispenser usage encouraged

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Dressing gowns
  • Hair dryer
  • Private bathroom
  • Shower
  • 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

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.
  • Cots (infant beds) are not available.

Payment types at the property

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Front desk staff will greet guests on arrival at the property.

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

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 631 out of 1004 reviews
Rating 8 - Good. 245 out of 1004 reviews
Rating 6 - Okay. 73 out of 1004 reviews
Rating 4 - Poor. 32 out of 1004 reviews
Rating 2 - Terrible. 23 out of 1004 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

Reviews

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

Khytie

Stayed 3 nights 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

10/10 Excellent

Joseph

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice
Stayed 1 night in Nov 2025

10/10 Excellent

Bianca

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Previously stayed prior to it being changed to Staypineapple. Love the renovations and new look. Beds were comfy and completely dog friendly. Staff are friendly and helpful. Plan on staying there again. Enjoyed my stay.
Stayed 4 nights in Oct 2025

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Oct 2025

8/10 Good

jeanne

Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
Clean and quiet. Small room, but good for a solo stay. Very nice linens. Do NOT appreciate the unwaivable, nonnegotiable amenity fee ($25 per day!!). Just be transparent and add this to the room rate--cut out the subterfuge!
Stayed 3 nights in Oct 2025

10/10 Excellent

Kristine

Stayed 2 nights in Oct 2025

10/10 Excellent

Dana

Stayed 1 night in Oct 2025

10/10 Excellent

John

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay
Stayed 2 nights in Oct 2025

2/10 Terrible

Justin

Disliked: Cleanliness, staff & service, property conditions & facilities, room comfort
We checked in and checked out within 15 minutes. The photos make the rooms appear much larger. In reality they are very small. No closets, only wall hooks. Minimal space to walk around the bed. Drawers under the bed are the only storage. The bathroom has a tiny pedestal sink with no counter space at all. The photos do not show the bathrooms accurately. We were in town for a wedding and there was no practical way to get ready in that room. The front desk agent, Reshawn, was professional and very kind. Hotels dot com contacted the property and the hotel agreed to cancel the stay and refund the first night since we did not stay. After we left they declined to honor that commitment. Because of this reversal I am compelled to write this review to warn others that the hotel did not follow through on what it promised.
Stayed 4 nights in Oct 2025