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Staypineapple, A Delightful Hotel, South End

3.0 star property
Hotel with a restaurant, a short walk to Copley Square
VIP Access

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

Enjoy dining al fresco at this charming street corner restaurant with a cozy outdoor seating area.
Enjoy a casual dining experience with a focus on comfort and style in this modern restaurant.
Relax in a stylish room with a large bed, a small window offering a view, and a decorative wall piece.
Check-in and unwind in our stylish lobby, featuring a digital display, elegant staircase, and a chandelier.
Step into the elegant lobby, featuring a classic checkered floor, a fireplace, and a unique coffee table.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Air conditioning

Explore the area

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
VIP Access
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  • Extra savings and perks for Rewards members
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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
(36 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

8.8 out of 10
Excellent
(6 reviews)
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Boston

Located in South End, Staypineapple, A Delightful Hotel, South End is within a 10-minute walk of popular sights such as Copley Square and Copley Place. This 56-room, 3-star hotel has in-room conveniences like iPod docks, coffee makers, and flat-screen TVs.

What's nearby

  • Copley Place - 7 min walk - 0.4 miles
  • Copley Square - 8 min walk - 0.5 miles
  • Newbury Street - 10 min walk - 0.5 miles
  • Boston Common - 13 min walk - 0.7 miles
  • Fenway Park - 2 min drive - 1.4 miles

Getting around

  • Back Bay Station - 6 min walk
  • Arlington Station - 8 min walk
  • Boston, MA (BNH-Boston Harbor Seaplane Base) - 17 min drive

Restaurants

  • ‪Club Cafe - ‬3 min walk
  • ‪Grill 23 & Bar - ‬4 min walk
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪Greystone Cafe - ‬5 min walk
  • ‪Clerys - ‬5 min walk

About this property

Staypineapple, A Delightful Hotel, South End

Hotel with a restaurant, a short walk to Copley Square
A local mainstay since 1900, Staypineapple, A Delightful Hotel, South End offers coffee in a common area and free use of bicycles. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
Guests can expect to find 50-inch flat-screen TVs with satellite channels. Pillowtop beds sport premium bedding and down comforters, and bathrooms offer hair dryers and designer toiletries. IPod docks, coffee makers, and free local calls are other standard amenities. Housekeeping is available on request.
Recreational amenities at the hotel include complimentary bicycles.

Languages

English, French, Spanish

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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

  • This property welcomes pets for USD 29.95 per pet, per night
  • Dogs only
  • 2 total pets
  • Food and water bowls are available
  • Certain rooms only, restrictions apply
  • Guests can request a pet-friendly room by contacting the property at the number on the booking confirmation
  • Service animals exempt from fees

Property payment types

Important information

Fees

You'll be asked to pay these 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

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

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

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4 PM
  • Check-out: noon
  • Minimum check-in age: 18
The front desk is open 24 hours a day.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • No parking is available onsite.
  • Tax ID number is C0014880350.
  • This property accepts credit cards. Cash is not accepted. 
  • Onsite safety features include a smoke detector.
  • Cashless payment methods are available for all transactions.

Additional information about polices, regulations, and more:

  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.
  • 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

Frequently asked questions

Is free cancellation available at Staypineapple, A Delightful Hotel, South End?

Staypineapple, A Delightful Hotel, South End offers free cancellation on certain room rates. For specific requirements, review the cancellation policy on our site.

How much does it cost to stay at Staypineapple, A Delightful Hotel, South End?

As of Jul 12, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Aug 4, 2025 start from $288.15, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What's there to do close to Staypineapple, A Delightful Hotel, South End?

This hotel is situated in South End within a 10-minute walk of Copley Square, Copley Place, and Newbury Street. You'll also find Boston Common and The Shops at Prudential Center less than a mile away.

Will I be able to park at Staypineapple, A Delightful Hotel, South End?

No, there isn't parking available at the hotel.

Does Staypineapple, A Delightful Hotel, South End have a casino on the premises?

No, Staypineapple, A Delightful Hotel, South End doesn't have a casino.

Will I find an indoor pool at Staypineapple, A Delightful Hotel, South End?

No, there is no indoor pool at this hotel.

What amenities will couples enjoy at Staypineapple, A Delightful Hotel, South End?

Amenities that appeal to couples at this boutique hotel include a pillowtop mattress, streaming services, and bathrobes.

Does Staypineapple, A Delightful Hotel, South End have a hot tub?

No, there isn't a spa tub at this hotel.

Does Staypineapple, A Delightful Hotel, South End feature a restaurant that includes a breakfast menu?

Yes, Staypineapple, A Delightful Hotel, South End serves brunch for a surcharge at Trophy Room.

Will Staypineapple, A Delightful Hotel, South End allow pets to stay for free?

Although they can't stay for free, dogs are welcome at Staypineapple, A Delightful Hotel, South End for a fee of USD 29.95 per pet, per night. The property also provides food and water bowls.

Are there connecting rooms at Staypineapple, A Delightful Hotel, South End?

No, this hotel doesn't feature connecting guestrooms.

How far is the airport from Staypineapple, A Delightful Hotel, South End?

The closest major airport to Staypineapple, A Delightful Hotel, South End is Logan International Airport (BOS), which is 4.5 mi away (7 minutes by car). Another top airport is Boston, MA (BNH-Boston Harbor Seaplane Base), which is located 5.3 mi away (17-minute drive).

Can I book a room with a balcony at Staypineapple, A Delightful Hotel, South End?

No, there aren't any guestrooms with balconies at Staypineapple, A Delightful Hotel, South End.

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 563 out of 954 reviews
Rating 8 - Good. 264 out of 954 reviews
Rating 6 - Okay. 72 out of 954 reviews
Rating 4 - Poor. 33 out of 954 reviews
Rating 2 - Terrible. 22 out of 954 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

Namthip

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

10/10 Excellent

Alexandra

Stayed 1 night in Apr 2025

8/10 Good

Keiko

Stayed 1 night in Apr 2025

10/10 Excellent

Wiley

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location with easy access to fun walkable neighborhoods and mass transit. Small rooms but as long as you know what to expect they’re entirely reasonable, with tasteful updates and nice amenities.
Stayed 5 nights in Apr 2025

8/10 Good

Victoria, Morganville

Liked: Staff & service, property conditions & facilities
Test
Stayed 1 night in Mar 2025

10/10 Excellent

Domenic

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was such a cute hotel! Perfect stay for a few days in Boston. It was in a nice neighborhood and close to transport to explore the city. I would recommend this hotel to anyone.
Stayed 3 nights in Mar 2025

10/10 Excellent

Manuel, Providence

Stayed 1 night in Dec 2024

10/10 Excellent

Katherine

Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such helpful staff!! And great with dogs
Stayed 1 night in Apr 2025

10/10 Excellent

Ryann

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great dtaff.
Stayed 1 night in Mar 2025

10/10 Excellent

Jacob

Stayed 1 night in Mar 2025

8/10 Good

Kiara

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

6/10 Okay

Kenneth

Disliked: Staff & service, room comfort
They did not clean my room after the first night; the bathroom fan would not turn off; the toilet plugged; no ice on my floor; downstairs bar had horrible beer offerings; room and bathroom are tiny
Stayed 3 nights in Mar 2025

8/10 Good

Chantal

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Mar 2025

10/10 Excellent

Kristine

Liked: Cleanliness, staff & service, property conditions & facilities
Super cute room. Definitely efficiency not much for storage so extended stays
Stayed 1 night in Mar 2025

10/10 Excellent

Christina

Traveled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I stayed here for the world figure skating championships with my dog, and my stay was excellent. Staff was very attentive, always friendly, and I definitely felt welcome and safe here. Staff went out of their way to accommodate guests based on my own experience and observation. Lauren was awesome and even recommended a dog bakery to me where I ended up purchasing treats for my dog. The other “everything people” also had great recommendations for dinner and the area is walkable and I felt safe at night as well. Subway (the “T”) is close by and an Uber is literally there anywhere from one to three minutes. The only caveat is parking; the parking garage is expensive and on-street parking is nearly impossible to find. But the hotel itself I give five stars to and would stay there again.
Stayed 4 nights in Mar 2025

8/10 Good

Mike

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Now that I know there’s an automatic amenity upcharge of $25/night for wifi and extra towels you get for free at other brands, I will be better at comparing rates.
Stayed 3 nights in Mar 2025

10/10 Excellent

Marc

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We found it to be a hugely pleasant surprise in all regards. Would seek it out again.
Stayed 3 nights in Mar 2025

10/10 Excellent

Amy

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

enjoyed this boutique hotel

As noted in descriptions the room was small but very well situated to be comfortable and functional. Amenities to meet the needs of a few days of travel, bright comfortable space, conveniently located.
Stayed 2 nights in Mar 2025

10/10 Excellent

Jesse

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

8/10 Good

Donald

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

3 nights in Boston

The hotel staff members were friendly and extremely helpful. The mattress and pillows were comfortable. We didn't like the system of separate duvets for each side of the bed, and the duvets slipped onto the floor during the night if you didn't lay perfectly still. We prefer a traditional system of a separate top sheet and bedspread that tuck into the bottom of the bed. Our sink drained very slowly and the auxiliary heater on the wall whined so loudly that we didn't use it. The other amenities, such as gifts of a water bottle and 2 drinks at the bar, in-room coffee, and afternoon cookies are nice touches. We wish we'd known when we booked that it has no parking for guests, but that may be typical of a middle-of-a-big-city boutique hotel.
Stayed 3 nights in Mar 2025

10/10 Excellent

Luke

Stayed 2 nights in Mar 2025

10/10 Excellent

Lori

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
StayPineapple is a lovely quirky hotel located in downtown Boston. Very walkable with affordable dining options close by. The rooms are spic and span with modern upgrades and ever so comfortable beds. Plus, it is a phenomenal bargain in an expensive world.
Stayed 2 nights in Mar 2025

8/10 Good

Karen

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

10/10 Excellent

Neri, NYC

Stayed 2 nights in Mar 2025

8/10 Good

Verified traveler

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

Not for everyone

To start, I would stay here again. However, I am not sure it would be the same for everyone. The room is VERY small. The bed takes up almost the entire space. There is no closet, just hooks on the wall. They do have some drawers under the bed but no dresser. They have USB plugs on the nightstands but they were all broken. The bathroom is also tiny and the squeeze between the shower door and sink is about 2.5 feet. A stout person would have a hard time getting into the shower. Water pressure was also poor--hard to get shampoo rinsed out. The room was very clean. The desk staff incredibly friendly and helpful. They give you perks like a welcome drink in the downstairs bar (beer and wine only) but they charge a $25 facility fee that offsets that nicety. Coffee in the lobby (no decaf) and cookies in the afternoon is a nice touch.
Stayed 2 nights in Mar 2025

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