See all properties

Staypineapple, A Delightful Hotel, South End

3.0 star property

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Reception
Bar (on property)
Lobby sitting area
Bar (on property)

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk
The current price is $259
includes taxes & fees
Jul 5 - Jul 6

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Square
    ‪6 min walk‬
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Boston Common
    ‪10 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪6 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)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.2 out of 10
Wonderful
(51 reviews)
  • 190 sq ft
  • Sleeps 2
  • 1 King Bed

Similar properties

Lobby sitting area
The Revolution Hotel
South End
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 2,660 reviews
The Revolution Hotel

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 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.

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
  • 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.
  • Elevator
  • Hardwood flooring in room
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk
  • Wheelchair-accessible restaurant

More

  • 1 building
  • 8 floors
  • Built in 1900
  • Fireplace in lobby
  • No plastic water bottles
  • Smoking not allowed
  • Water dispenser usage encouraged

Room amenities

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • 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 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

9.0

Wonderful

Rating 10 - Excellent. 650 out of 1006 reviews
Rating 8 - Good. 228 out of 1006 reviews
Rating 6 - Okay. 71 out of 1006 reviews
Rating 4 - Poor. 31 out of 1006 reviews
Rating 2 - Terrible. 26 out of 1006 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.8/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Fernando

Wonderful stay
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Neil

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Thoroughly enjoyed my stay here. Excellent value.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Simeng

Liked: Cleanliness, property conditions & facilities
the staff is excellent!
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Hortencia

Liked: Cleanliness, staff & service, amenities
Clean and great location. Wonderful service. Really enjoyed our stay and will return.
Stayed 3 nights in Nov 2025
Verified

8/10 Good

Karen

Liked: Cleanliness, staff & service, amenities
Great location cute bar. Room small but good use of space
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities
The cleanliness of the entire property was above average, the friendliness was fantastic
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Aimee

Liked: Cleanliness, amenities, property conditions & facilities
Super cute room staff was great
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Skyler

Liked: Cleanliness, amenities, property conditions & facilities
Everyone was very kind and accommodating! Rooms were so cozy and clean. Would definitely stay again.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Jasmyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs!
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

John

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

10/10 Excellent

Joy

Liked: Cleanliness, amenities, property conditions & facilities
Loved this hotel. Convenient to everything, nice staff , rooms had everything you could need and the bed was very cozy. Loved the free reusable water bottle and the complimentary cocktail at the bar . Highly recommend
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Jan S

Liked: Cleanliness, amenities, property conditions & facilities
We've been to several Staypineapple hotels and they're always great. Clean rooms with comfortable beds and nice little extras that make the stay more pleasant.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

waileong

Liked: Cleanliness, staff & service, amenities
staff and room are great
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Rod

Liked: Cleanliness, staff & service, amenities
Yes it was spotless and well organized.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Dandre

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was absolutely amazing and met all needs.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Karen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay when in Boston
Stayed 2 nights in Oct 2025
Verified

6/10 Okay

Taisha

Disliked: Cleanliness
Nice area and the staff were really nice but when we checked the room the sheets had stains and so did the towels & robe.
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

vasilios

Liked: Cleanliness, staff & service, property conditions & facilities
Making Pineapples Great Again
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Jan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We always enjoy the Staypineapple experience. Nice room, comfortable, clean and great service. Good location only a few minute walk to the Metro.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Theresa

Liked: Cleanliness, staff & service, amenities
clean, cute, great location, parking garage minutes away
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Janina

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The beds were incredibly comfortable. We loved the individual duvets. The decor and ambiance were amazing. The staff was kind. The snack pack upgrade was very disappointing and sparse vs the picture. However, the overall experience was memorable.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Loren

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Cute room, kind staff, great location.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Genesse

Liked: Cleanliness, staff & service, property conditions & facilities
It was such a cozy place to stay. Would def stay here again
Stayed 3 nights in Oct 2025
Verified

8/10 Good

steven louis

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent staff, incredible location for walking around town.
Stayed 3 nights in Sep 2025
Verified

8/10 Good

Mikita

Liked: Cleanliness, amenities, property conditions & facilities
Room was spotless but would be nice if they offer extra bottles of water
Stayed 5 nights in Jan 2026