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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

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • Air conditioning

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Square
    ‪8 min walk‬
  • Place, Boston Common
    ‪13 min walk‬
  • Place, Fenway Park
    ‪2 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪5 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, a quick 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 on-site. Housekeeping is available on request.
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with iPod docking stations and complimentary bottles of water. 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). Additionally, rooms include coffee/tea makers and a hairdryer. 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 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 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

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
  • Smoke-free property

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

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

Reviews

Staypineapple, A Delightful Hotel, South End Reviews

8.8

Excellent

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness
Rating 10 - Excellent. 610 out of 1011 reviews
Rating 8 - Good. 269 out of 1011 reviews
Rating 6 - Okay. 72 out of 1011 reviews
Rating 4 - Poor. 36 out of 1011 reviews
Rating 2 - Terrible. 24 out of 1011 reviews

Reviews

10/10 Excellent

Diane

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in Jul 2025

8/10 Good

Justin, Round Lake

Liked: Cleanliness, staff & service, property conditions & facilities
Rooms are small. People are nice .
Stayed 3 nights in Jul 2025

10/10 Excellent

Nollie

Liked: Cleanliness, amenities, property conditions & facilities
Stayed 3 nights in Jul 2025

8/10 Good

Karen

Travelled with family
Liked: Cleanliness, amenities
Great staff and great location, convenient to trains and subway. Fun bar in the lobby connected to the hotel. Very comfy beds.
Stayed 3 nights in Jul 2025

4/10 Poor

Karine

Business traveller
Stayed 3 nights in Jun 2025

10/10 Excellent

Lisa

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

I was indeed delighted!

This place truly is delightful! The decor is charming, yellow accents and pineapple-y. The bedding is SO comfortable. I ended up not feeling well one day and didn’t mind staying in bed for half a day. The room was so cozy! The hotel doesn’t have a microwave or fridge for guests to use, either in rooms or communally, so be forewarned. The loaner bikes are a nice touch and come in handy for a quick ride along the River Charles.
Stayed 2 nights in Jul 2025

8/10 Good

Ron

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

Not staying here again for the price.

Room was too small, and noisy next to the stairs.
Stayed 4 nights in Jun 2025

10/10 Excellent

Kristi

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Jun 2025

8/10 Good

Elizabeth

Stayed 4 nights in Jul 2025

10/10 Excellent

Jill

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Friendly, knowledgeable and accommodating staff. A very cute room!!
Stayed 3 nights in Jun 2025

8/10 Good

Brett

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

Great time in the south end

We had a great stay at Staypineapple Boston! The staff was truly amazing—friendly, helpful, and made us feel very welcome. The location is fantastic, perfect for exploring the city. A couple of small issues like holes in the blinds and some city noise at night, but overall, a really enjoyable experience.
Stayed 4 nights in Jun 2025

6/10 Okay

STEPHEN, AMSTON

Stayed 2 nights in Jun 2025

10/10 Excellent

Holly

Stayed 4 nights in Jun 2025

8/10 Good

Walter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great option within walking distance to downtown
Stayed 3 nights in Jun 2025

8/10 Good

Michael

Liked: Staff & service, room comfort
Stayed 1 night in Jun 2025

10/10 Excellent

Holly

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

Friendly Staff

Both the staff at the hotel and the Trophy Room restaurant were absolutely amazing!! Beds were very comfortable and we liked the location
Stayed 3 nights in Jun 2025

4/10 Poor

Douglas

Stayed 1 night in Jun 2025

8/10 Good

Jade

Business traveller
Liked: Cleanliness, staff & service, amenities
Super nice staff! Like the free water bottle for fill ups. Like the area / food abundant. But room super small and lots of noise from street and thin windows/walls.
Stayed 4 nights in Jun 2025

8/10 Good

Simon

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
I was in town for a conference.
Stayed 4 nights in Jun 2025

10/10 Excellent

Carrie

Business traveller, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
had a wonderful experience. Very cozy and comfortable love the ambience like The Restaurant was attached to it totally recommend.
Stayed 4 nights in May 2025

10/10 Excellent

Mary

Travelled with partner, Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Small room but they make the most of the space. Beds, pillows, linens, and towels comfortable. A/C is low noise. Hotel is on a culdesac so street noise is minimal, but did here the train once. Windows are not very sound proof, but didn't hear room neighbors. Close to many great restaurants, coffee and 7-11. Subway about a 12 minute walk. But walk is over cobblestone so beware of rolling luggage. Staff was friendly and helpful. Bar was handy, but didn't eat at the grill. Would recommend and stay here again.
Stayed 4 nights in Jun 2025

8/10 Good

Kelly

Liked: Cleanliness, staff & service, property conditions & facilities
I stayed for 13 nights. Very friendly front desk staff, loved the bedding, location was great (a few blocks from Back Bay subway stop). The water bar was helpful, morning coffee always good, and loved the afternoon cookies. A dry cleaner right across the street that does wash and fold. Also great if you need a late check out (noon). The negatives- TINY rooms, no mini fridge/microwave, and shower had poor water pressure. Overall, a good stay at a good value- this was one of the more reasonably priced hotels. I would stay again!
Stayed 12 nights in Jun 2025

8/10 Good

Fullando

Liked: Cleanliness, staff & service, amenities
This is very cute hotel nestled in a quiet residential area next to everything.
Stayed 3 nights in Jun 2025

10/10 Excellent

Gina, KANSAS CITY

Stayed 4 nights in Jun 2025

10/10 Excellent

Cyndie

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Food is great here... Rooms are super cute.
Stayed 6 nights in Jun 2025