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Staypineapple, A Delightful Hotel, South End

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

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • Pet friendly
  • Air conditioning
  • Restaurant

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
VIP Access
Curated for quality and service, VIP Access stays consistently receive our highest guest ratings.
  • Expect exceptional service
  • 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
(45 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 the neighborhood

Boston

Located in South End, Staypineapple, A Delightful Hotel, South End is a leisurely stroll from popular sights such as Copley Square and Boston Common. This 56-room, 3-star hotel welcomes guests with in-room amenities like iPod docks, coffee makers, and flat-screen TVs.

What's nearby

  • Copley Square - 8 min walk - 0.5 miles
  • Boston Common - 13 min walk - 0.7 miles
  • Fenway Park - 2 min drive - 1.4 miles
  • New England Aquarium - 2 min drive - 1.4 miles
  • TD Garden - 4 min drive - 2.2 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
  • ‪The Friendly Toast - ‬4 min walk
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪Trophy Room - ‬1 min walk
  • ‪Flour Bakery + Cafe - ‬4 min walk

About this property

Staypineapple, A Delightful Hotel, South End

Hotel with a restaurant, a quick 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.

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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 Sep 14, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Sep 21, 2025 start from $279.0, 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, there isn't parking at this 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.

Is Staypineapple, A Delightful Hotel, South End a good place to stay for couples?

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, there aren't connecting guestrooms at this hotel.

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).

Are there rooms with balconies that I can book at Staypineapple, A Delightful Hotel, South End?

No, you won't find guestrooms with balconies at Staypineapple, A Delightful Hotel, South End.

Reviews

Staypineapple, A Delightful Hotel, South End Reviews

8.8

Excellent

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness
Rating 10 - Excellent. 599 out of 1001 reviews
Rating 8 - Good. 270 out of 1001 reviews
Rating 6 - Okay. 73 out of 1001 reviews
Rating 4 - Poor. 36 out of 1001 reviews
Rating 2 - Terrible. 23 out of 1001 reviews

Reviews

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

10/10 Excellent

Elizabeth

Traveled with family
Liked: Cleanliness
Very comfortable beds!!! Maintenance fixed a clogged sink right away. Run vibes in the bar downstairs.
Stayed 2 nights in May 2025

10/10 Excellent

mark

Stayed 1 night in Jun 2025

10/10 Excellent

Nicole

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone that worked there was incredibly kind. It was my husbands birthday and they made a towel cake for him with balloons and a little party hat on their plushie mascot. The bar was great, especially because you get a free welcome drink which is awesome! Would 100% recommend. Walkable, good options near by. I also recommend Barcelona, it’s a tapas bar near by, went 2 times in the 4 days I was there!! 100/100!
Stayed 3 nights in Apr 2025

8/10 Good

Emily

Liked: Staff & service, room comfort
Stayed 3 nights in Apr 2025

10/10 Excellent

JANET

Traveled with family
Liked: Cleanliness, staff & service, room comfort
Stayed 4 nights in May 2025

6/10 Okay

Sukhjit

Liked: Cleanliness, property conditions & facilities
Stayed 6 nights in May 2025

10/10 Excellent

Dean

Stayed 3 nights in May 2025

10/10 Excellent

Melissa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved our stay here! The hotel is great & the bar was super fun! The location was great, an easy walk to wherever you want go!
Stayed 2 nights in May 2025

10/10 Excellent

Ronald

Stayed 1 night in May 2025

4/10 Poor

Bethlehem

Meh
Stayed 3 nights in May 2025

10/10 Excellent

Lisa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun hotel with unique decor. Would stay there again
Stayed 2 nights in May 2025

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, property conditions & facilities
Great area.
Stayed 3 nights in May 2025

10/10 Excellent

Renee

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Love it here!
Stayed 2 nights in May 2025

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