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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

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Photo gallery for Staypineapple, A Delightful Hotel, South End

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

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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Room options

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

8.8 out of 10
Excellent
(34 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 luggage storage and concierge services. 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
  • Proposal/romance packages
  • 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
  • Smoke-free property

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 Jun 25, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Jul 7, 2025 start from $228.65, 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.

Is there parking available at Staypineapple, A Delightful Hotel, South End?

No, this hotel doesn't offer parking.

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 will couples enjoy most about a stay at Staypineapple, A Delightful Hotel, South End?

This boutique hotel offers plenty of amenities for couples including a bar, a restaurant, and proposal/romance packages.

Are there hot tubs at Staypineapple, A Delightful Hotel, South End?

No, this hotel doesn't have a spa tub.

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.

Does Staypineapple, A Delightful Hotel, South End have connecting rooms?

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, you won't find guestrooms with balconies at Staypineapple, A Delightful Hotel, South End.

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 554 out of 937 reviews
Rating 8 - Good. 257 out of 937 reviews
Rating 6 - Okay. 72 out of 937 reviews
Rating 4 - Poor. 32 out of 937 reviews
Rating 2 - Terrible. 22 out of 937 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

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

10/10 Excellent

Luzviminda D

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Convenience to public transportation especially since we took the Amtrak from NYC. Walking distance to places we liked to see - Boston Public Library, Boston Public Garden, Boston Common, Charles River Esplanade, cafes on Beacon Hill, Acorn Street, Cathedral of the Holy Cross and many more. Staff was very friendly and warm and even allowed us early check-in with complimentary drinks… also they’re dog-friendly.
Stayed 1 night in Mar 2025

10/10 Excellent

Verified traveler

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

The pineapple is sweet.

cute little place in the middle of Boston. good location easy for taxi pick ups.
Stayed 2 nights in Mar 2025

10/10 Excellent

Nancy, DUBLIN

Stayed 1 night in Mar 2025

10/10 Excellent

Cam

Stayed 1 night in Dec 2024

10/10 Excellent

Tracy

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This hotel was in a great location. The town had many shopping and dining locations. The staff were very friendly and accommodating. I would stay here again when visiting the Boston area. The parking garage was less than a 10 minute walk and the property does offer a loading station to temporarily park your car so you aren’t hauling all your luggage.
Stayed 2 nights in Mar 2025

10/10 Excellent

Krystle

Stayed 2 nights in Mar 2025

8/10 Good

ivo

Liked: Cleanliness, property conditions & facilities, room comfort
Stayed 3 nights in Nov 2024

10/10 Excellent

Susan

Great fun!

a great little hotel in the South End - very convenient to Back Bay - my room was very comfortable and clean.
Stayed 2 nights in Mar 2025

10/10 Excellent

Luisa, Weston

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Definitely a great place to stay at a great value, close to various T stations which make it really convenient if you are not driving. The rooms are gorgeous and comfortable. You get free refill of coffe and water as you please
Stayed 6 nights in Mar 2025

6/10 Okay

Israel, temecula

Business traveler
Liked: Cleanliness, staff & service
limited dining only lunch and dinner no breakfast limited amenities not good for business meetings
Stayed 3 nights in Mar 2025

10/10 Excellent

KATHLEEN

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

4/10 Poor

Madison

Business traveler
Disliked: Cleanliness, property conditions & facilities

Just okay

This hotel needs a renovation. It was OK but pretty worn and not particularly clean. The robe had someone else's hair in it, and the sheets had random fluff on them.
Stayed 3 nights in Mar 2025

10/10 Excellent

Alejandra

Stayed 4 nights in Mar 2025

8/10 Good

Vladimir

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Feb 2025

10/10 Excellent

FULVIO

Stayed 1 night in Mar 2025

10/10 Excellent

Shaylia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely loved my stay easy pretty clean
Stayed 1 night in Feb 2025

10/10 Excellent

Nicholas, FRIDLEY

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
.
Stayed 4 nights in Feb 2025

10/10 Excellent

Hayden

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

10/10 Excellent

Joel

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

6/10 Okay

Ugur Yigit

Liked: Staff & service
Stayed 2 nights in Feb 2025

10/10 Excellent

Leah

Liked: Cleanliness
Stayed 4 nights in Feb 2025

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