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Staypineapple, A Delightful Hotel, South End

3.0 star property
3-star boutique hotel near Copley Square

Choose dates to view prices

Photo gallery for Staypineapple, A Delightful Hotel, South End

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

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

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

Heart of Boston.Within a 10-minute walk of this South End hotel, you'll find Copley Square and Copley Place. Also, Newbury Street is within half a mile (1 km) and Boston Common is within 2 miles (3 km).

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

3-star boutique hotel near Copley Square
There's a restaurant on site. You can enjoy a drink at the bar/lounge. Multilingual staff, tour/ticket assistance, and coffee/tea in a common area are also featured at the business-friendly Staypineapple, A Delightful Hotel, South End.

This 3-star Boston hotel is smoke free.

  • 1 building
  • 56 guestrooms or units
  • 8 levels
  • Built in 1900
  • Coffee in lobby
  • Front desk (24 hours)
  • Staff is multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Elevator
  • No smoking on site
  • Bar or lounge
  • Dining venue
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.

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

Things to do

  • Free bicycle rentals

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

Room amenities

Entertainment

  • 50-inch flat-screen TV with cable/satellite channels
  • iPod dock
  • Streaming services

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

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: USD 29.95 per pet, per night
  • Only dogs are allowed
  • Maximum 2 pets
  • Food and water bowls are available
  • Certain rooms only, restrictions apply
  • You can request a pet-friendly room by reaching out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

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

Guests will be asked to pay the following 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

We've listed all charges provided to us by the property.

Optional extras

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

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

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. No onsite parking is available. The tax ID number is C0014880350. This property accepts Visa, Mastercard, American Express, Discover, Diners Club, and Union Pay. Cash is not accepted. For guests' safety, the property includes a smoke detector in each accommodation. Cashless payment methods are available for all transactions.

We should mention

  • Pets are welcome in certain rooms only; other restrictions apply (please see the Fees section for related charges). To make arrangements for your pet, contact the property directly at the number on your booking confirmation.
  • 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

How close is Staypineapple, A Delightful Hotel, South End to the airport?

Staypineapple, A Delightful Hotel, South End is 5.3 mi (17-min drive) away from the Boston, MA (BNH-Boston Harbor Seaplane Base) airport, the closest popular airport to the property.

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

As of Jun 22, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Jul 2, 2025 start from $145.0, 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.

Does Staypineapple, A Delightful Hotel, South End have an airport shuttle?

Airport shuttle services are not available at Staypineapple, A Delightful Hotel, South End.

How close is Staypineapple, A Delightful Hotel, South End to the beach?

This hotel is a short 8-minute walk from Carson Beach and 8.7 mi (25-min drive) from Revere Beach. Don't forget your sunscreen!

Does Staypineapple, A Delightful Hotel, South End offer free breakfast?

Staypineapple, A Delightful Hotel, South End does not offer free breakfast.

Is there a casino at Staypineapple, A Delightful Hotel, South End?

No, there is no casino at this hotel, but Encore Boston Harbor (9-min drive) is nearby.

What time is check-in at Staypineapple, A Delightful Hotel, South End?

Check-in start time: 4 PM; Check-in end time: midnight.

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

Free parking is not available at this hotel.

Does Staypineapple, A Delightful Hotel, South End have a pool?

Staypineapple, A Delightful Hotel, South End does not have a pool.

Does Staypineapple, A Delightful Hotel, South End have a restaurant?

Staypineapple, A Delightful Hotel, South End is home to Trophy Room, which features American cuisine and brunch.

Does Staypineapple, A Delightful Hotel, South End have a spa?

There are no spa services available at this hotel.

How close is Staypineapple, A Delightful Hotel, South End to downtown Boston?

Staypineapple, A Delightful Hotel, South End is 1 mi away from Boston.

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

10/10 Excellent

Seyda

Stayed 1 night 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

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