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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
Premium bedding, down duvets, pillow-top beds, desk
Reception
Bar (on property)
Lobby sitting area

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • 24/7 front desk
  • Bar
  • Air conditioning

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Place
    ‪6 min walk‬
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Copley Square
    ‪8 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪4 min drive‬
VIP Access
Curated for quality and service, VIP Access stays consistently receive our highest guest ratings.
  • Expect exceptional service
  • 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
(46 reviews)
  • Sleeps 2
  • 1 King Bed

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About this property

Staypineapple, A Delightful Hotel, South End

Hotel with a restaurant, 9-minute walk to Copley Square
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 onsite. Housekeeping is available on request.
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with iPod docking stations and complimentary bottled water. 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). Additionally, rooms include coffee/tea makers and hair dryers. Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided on request.

Recreational amenities at the hotel include complimentary bicycles.
Our customers tell us 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 like a restaurant, a bar, and concierge services. This property offers pet-friendly amenities like food and water bowls.
  • Enjoy American cuisine while dining at Trophy Room
  • Services include a concierge, tour or ticket assistance, and luggage storage
  • Onsite recreation includes complimentary bicycles
  • Guests have great things to say about the clean accommodations and the helpful staff
  • Within a 15-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 a 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 specializes 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 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.

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.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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. 616 out of 1000 reviews
Rating 8 - Good. 252 out of 1000 reviews
Rating 6 - Okay. 73 out of 1000 reviews
Rating 4 - Poor. 35 out of 1000 reviews
Rating 2 - Terrible. 24 out of 1000 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

10/10 Excellent

Rebecca

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very unique. Truly delightful experience!
Stayed 2 nights in Aug 2025

10/10 Excellent

Marybeth

Liked: Cleanliness, staff & service, property conditions & facilities
Room was cozy
Stayed 2 nights in Aug 2025

8/10 Good

James

Liked: Cleanliness, staff & service
Disliked: Amenities, property conditions & facilities
Tiny toilet
Stayed 4 nights in Sep 2025

10/10 Excellent

Emily

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property was in such a great area and walkable distance to many sights in Boston. I traveled for a birthday and they accommodated decorations free of charge. The staff were on site late into the night and available to help. Room was comfortable and the Trophy Room restaurant on the bottom floor was nice and LGBTQ+ friendly.
Stayed 4 nights in Aug 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great area & hotel

Loved the hotel, gay friendly area as well. Super cute, will stay again!
Stayed 2 nights in Aug 2025

10/10 Excellent

Michael, Washington

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

6/10 Okay

shelley, Newport Beach

Liked: Cleanliness, staff & service
Disliked: Amenities
Rooms are very small, restaurant bar was just below our room and open til 1am-very loud, restaurant for breakfast has very limited menu and coffee is terrible.
Stayed 1 night in Aug 2025

4/10 Poor

Tico

Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
The guest “amenity” charge is outrageous, especially at $24.95 per day. I used no amenities aside from the one water bottle that states it’s complimentary on the tag and the three coffee pods that were provided. I didn’t have housekeeping come into my room, so nothing was replenished, so what exactly am I being charged for at such a rate times three? What amenities? Quite frankly, $24.95 a day is exorbitant for what is "provided." And especially when all I had is the water and three coffee pods for all three days/nights. I would much rather pay for what I actually use than be charged for what I don't under the guise of friendly service/convenience. But it is what it is. Now I know not to stay at another one of thrse locations during my next travels. Very disappointing. Because I did like the hotel, but what I don't like is the pretense of"pineappley" service when it's just blatant highway robbery.
Stayed 3 nights in Aug 2025

8/10 Good

maria elena sanchez

Liked: Cleanliness
Stayed 2 nights in Jul 2025

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic spot for the price, it was super clean and cute! Only downside is no parking, but there was plenty of spots near it to park at. 10/10 experience and staff was super nice
Stayed 1 night in Aug 2025

8/10 Good

Candice

Business traveller
Liked: Staff & service
Stayed 4 nights in Aug 2025

8/10 Good

Hailey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was nice
Stayed 3 nights in Aug 2025

6/10 Okay

james

Liked: Cleanliness, staff & service, room comfort
Stayed 3 nights in Jul 2025

10/10 Excellent

Scott

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in May 2025

10/10 Excellent

Taylor

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

What a fun, lovely, independent hotel.

What a cute hotel! Great location, clean rooms, love all the attention to details, plus the free reusable water bottle is amazing! Omg and the bed is SO COMFY. I would stay here in a heartbeat, and actually added another night at the hotel instead of staying with friends it’s that good.
Stayed 1 night in Aug 2025

10/10 Excellent

Ryan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jul 2025

10/10 Excellent

Roy

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room had many thoughtful details that made the cozy room practical. The Staff was very helpful, even let us borrow an umbrella when in suddenly started raining at the time we had dinner reservations a few blocks away. We enjoyed using the bicycle. Late Check out time was nice to.
Stayed 4 nights in Aug 2025

10/10 Excellent

Giovanna

Liked: Cleanliness, staff & service, property conditions & facilities
Friendly staff
Stayed 3 nights in Aug 2025

10/10 Excellent

Taylor

Business traveller
Liked: Cleanliness, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

Tim

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this property. A lot of detail has gone into the decor. Staff very welcoming.
Stayed 2 nights in Aug 2025

10/10 Excellent

David

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was small but felt so good. Room was clean and staff was super friendly
Stayed 2 nights in Aug 2025

10/10 Excellent

Derek

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Just thought was excellent location.
Stayed 2 nights in Aug 2025

10/10 Excellent

Nick

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We really enjoyed the stay here. Very clean, friendly staff, good location. Highly recommend.
Stayed 4 nights in Jul 2025

10/10 Excellent

Thomas

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

Clelia Maria

Liked: Cleanliness, staff & service, property conditions & facilities
Great location
Stayed 5 nights in Jul 2025