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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • Pet friendly
  • Air conditioning
  • Restaurant
$261
includes taxes & fees
Sep 1 - Sep 2

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Copley Square
    ‪8 min walk‬
  • Boston Common
    ‪13 min walk‬
  • Fenway Park
    ‪2 min drive‬
  • 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
(42 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

8.4 out of 10
Very good
(7 reviews)
  • Sleeps 2
  • 1 King Bed

Similar properties

Deluxe Room, 2 Double Beds (Bath in Room) | 1 bedroom, premium bedding, down comforters, pillowtop beds

The Revolution Hotel

  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 2,134 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 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.

Languages

English, French, Spanish

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. 593 out of 1000 reviews
Rating 8 - Good. 273 out of 1000 reviews
Rating 6 - Okay. 75 out of 1000 reviews
Rating 4 - Poor. 36 out of 1000 reviews
Rating 2 - Terrible. 23 out of 1000 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

10/10 Excellent

Tara

Liked: Amenities, property conditions & facilities
We loved this place close and convenient to most things in Boston all the little extras And the bed!
Stayed 3 nights in May 2025

10/10 Excellent

Courtney

Stayed 3 nights in May 2025

2/10 Terrible

Xiaohang

Disliked: Cleanliness
Very awful and unsafe place :(
Stayed 2 nights in May 2025

8/10 Good

Sue, SPRINGFIELD

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Cute little hotel. Staff was great. Room was small but arranged nicely. Amazing bedding. I want to buy a comforter. Very walkable. The bar on the first floor had great service and wonderful drinks. Like the coffee shop around the corner too.
Stayed 2 nights in May 2025

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, property conditions & facilities
Loved this quirky boutique hotel. It has great character, very clean, great walkable location. In south end - convenient to shopping and Fenway!
Stayed 1 night in Apr 2025

10/10 Excellent

Susana

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exceedingly good! We are so impressed with the concept and attention to detail in service and comfort. We will definitely choose Staypineapple when available.
Stayed 2 nights in May 2025

8/10 Good

Brian

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
The rooms are small, but very clean and comfortable.
Stayed 1 night in May 2025

6/10 Okay

Sherryl

Traveled with family
Liked: Cleanliness, staff & service
Cute, eclectic hotel, however it's geared more for one person per room than two. A little tight and no place to put things. For me personally, I thought the price was a little high for the offering and amenities, especially when we got there and found out there was another $87 charge for amenities(?). It's an older hotel with some things in the room still needing update. The staff I encountered were very nice and helpful. A single person probably would find it suitable, but I would look for a different hotel if visiting the city again.
Stayed 3 nights in May 2025

10/10 Excellent

Vivek

Stayed 2 nights in May 2025

6/10 Okay

Jon

Liked: Cleanliness, property conditions & facilities, room comfort

Would consider Pineapple chain in future

Overall it’s a nice boutique hotel and a good location for walking and transportation. The single biggest issue is with “resort fees” while this was refunded this time, it’s such a stain on the overall experience. If you are required to pay it, it should show in the total price initially.
Stayed 3 nights in Mar 2025

10/10 Excellent

Jim

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Very central
Stayed 5 nights in May 2025

6/10 Okay

andrew

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities, room comfort
The surrounding area was great, however,the room was as small as a shoe box! The service was friendly and helpful.
Stayed 2 nights in May 2025

10/10 Excellent

Caitlin

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This hotel is so cute! It was a great location to everything!
Stayed 3 nights in Apr 2025

2/10 Terrible

James

Stayed 4 nights in May 2025

8/10 Good

MARK

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

The definition of funky

Right after cool, offbeat, quirky, and unconventional in the list of synonyms for “funky” there should be a picture of the Staypineapple in Boston.
Stayed 1 night in May 2025

10/10 Excellent

Kim

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

Cute and fun

This is a cute, fun hotel. It is in a great location. Also offers a restaurant and bar. I love the bedding.
Stayed 2 nights in May 2025

10/10 Excellent

Barbara

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely amazing bedding - very comfortable! We will definitely stay again - very walkable to the Boston Commons, shopping, restaurants and theater. Staff were very nice and personable. A wonderful stay.
Stayed 2 nights in May 2025

6/10 Okay

Verified traveler

Liked: Cleanliness

Disappointed

Wanted to give it the benefit of the doubt since I went in knowing the rooms are small etc. The bathroom was EXTREMELY small though- hard to even wash your face in the sink. The biggest irritation was a daily $25 amenities fee for things that really should already be included- water bottle refills, in room coffee, wifi. It might be worth it if you plan to use the bikes? Otherwise it felt like a scam. Also the coffee cups weren’t cleaned on the every other day room cleaning & coffee wasn’t replaced either.
Stayed 4 nights in Apr 2025

10/10 Excellent

Mario

Business traveler
Liked: Staff & service, amenities
"Housekeeping only came every other day. However, the hotel and the service are good—well located and everyone is friendly. It's expensive, but I think it's one of the best options compared to other hotels."
Stayed 4 nights in May 2025

6/10 Okay

Allan

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

Say as it is

It’s a budget hotel and you get what you pay for. Staff cordially friendly. Room small, with nowhere to sit. Limited TV services and open to everyone WIFI. Reasonably placed to get into the Boston tourist area, approx a mile walk. Noisy as close to a freeway and train station (there again Boston is a noisy city)
Stayed 3 nights in May 2025

10/10 Excellent

Robert

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful, quaint hotel. Very nice location in residential, walkable city neighborhood. Staff is very friendly and helpful. Nice bar in the lobby that was not too loud. Only complaint was a single cockroach that visited our bathroom.
Stayed 2 nights in May 2025

10/10 Excellent

Andrea

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the decor and the bikes to ride around the city!
Stayed 1 night in May 2025

8/10 Good

Cheryl

Liked: Cleanliness, property conditions & facilities, room comfort
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very kind staff. Awesome bar connected and great food. Would stay again!
Stayed 1 night in Apr 2025

8/10 Good

Helen

Stayed 2 nights in Apr 2025