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Staypineapple, A Delightful Hotel, South End

3.0 star property

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Photo gallery for Staypineapple, A Delightful Hotel, South End

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • Air conditioning
$321
includes taxes & fees
Oct 30 - Oct 31

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

Room options

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

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

View all photos for South End Corner King

Premium bedding, down comforters, pillowtop beds, desk

South End Corner King

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

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About this property

Staypineapple, A Delightful Hotel, South End

3-star hotel in 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 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.
The hotel offers a restaurant. A bar/lounge is on site where guests can unwind with a drink. This business-friendly hotel also offers multilingual staff, tour/ticket assistance, and coffee/tea in a common area.

Staypineapple, A Delightful Hotel, South End is a smoke-free property.

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 transportation

  • No onsite 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.
  • Elevator
  • 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
  • Smoking not allowed

Room amenities

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • 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

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 29.95 per pet, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Specific rooms only, restrictions apply; pet-friendly rooms can be requested by contacting the property at the number on the booking confirmation
Food and water bowls are available

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

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • 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 have included all charges provided to us by the property.

Optional extras

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

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

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

We should mention

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

8.8

Excellent

Rating 10 - Excellent. 610 out of 1019 reviews
Rating 8 - Good. 275 out of 1019 reviews
Rating 6 - Okay. 74 out of 1019 reviews
Rating 4 - Poor. 36 out of 1019 reviews
Rating 2 - Terrible. 24 out of 1019 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

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

Traveled 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

Traveled 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 traveler
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 traveler
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

Traveled with group, Business traveler
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

Traveled with group, Traveled with partner
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

Traveled 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

8/10 Good

Chris

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

10/10 Excellent

Raven

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My first Staypineapple hotel and now I’m in love!
Stayed 3 nights in May 2025

10/10 Excellent

Alice

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great little hotel. Friendly, front desk service. Great location to walk to all the sights. Clean and comfy. Small but perfect for a couples stay.
Stayed 5 nights in Jun 2025

8/10 Good

DAVID

Stayed 3 nights in Jun 2025

10/10 Excellent

Ryan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great location, friendly staff, and comfortable rooms. Yes, the rooms are smaller than average, but only if you're expecting American-style hotel rooms (which waste a lot of space). It was plenty spacious, and very comfortable.
Stayed 4 nights in May 2025

10/10 Excellent

shiva

Liked: Cleanliness, property conditions & facilities
Stayed 2 nights in Jun 2025

8/10 Good

Namthip

Business traveler, Traveled with family
Liked: Cleanliness, amenities
Stayed 3 nights in May 2025

10/10 Excellent

Violeta

Traveled with group, Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very cute room, stayed a couple nights and everything was pleasant. Close to many good restaurants and cafes. Staff was excellent. I would recommend to a single or couple, short walk to the train and bus lines. Bring your water bottle, they have a refill station in the lobby.
Stayed 4 nights in Jun 2025

10/10 Excellent

Hector

Stayed 2 nights in Jun 2025

10/10 Excellent

Federica

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