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

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Newbury Street
    ‪8 min walk‬
  • Place, Copley Square
    ‪8 min walk‬
  • Place, Boston Common
    ‪13 min walk‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪4 min drive‬

Room options

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

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.0 out of 10
Wonderful
(46 reviews)
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Boston

Heart of Boston.Within a 15-minute walk of this South End hotel, you'll find Copley Square and Boston Common. Fenway Park and New England Aquarium are also within 2 miles (3 km).

What's nearby

  • Copley Place - 6 min walk - 0.4 miles
  • Newbury Street - 8 min walk - 0.5 miles
  • Copley Square - 8 min walk - 0.5 miles
  • The Shops at Prudential Center - 10 min walk - 0.6 miles
  • Boston Common - 13 min walk - 0.7 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 Café - ‬3 min walk
  • ‪The Friendly Toast - ‬4 min walk
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪Flour Bakery + Cafe - ‬4 min walk
  • ‪Trophy Room - ‬1 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
  • Water dispenser
  • 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.

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Charlesmark Hotel
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  • Free WiFi
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4.4 out of 5, Excellent, 1,131 reviews
$119 nightly
The price is $137
Jan 11 - Jan 12
Total with taxes and fees
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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
Information provided by the property may be translated using automated translation tools

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 Jan 8, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Jan 19, 2026 start from $84.49, 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 8.7 mi (25-min drive) from Revere Beach.

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

9.0

Wonderful

Rating 10 - Excellent. 622 out of 1000 reviews
Rating 8 - Good. 251 out of 1000 reviews
Rating 6 - Okay. 72 out of 1000 reviews
Rating 4 - Poor. 32 out of 1000 reviews
Rating 2 - Terrible. 23 out of 1000 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

JEAN-CHRISTOPHE

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice little hotel located in Back Bay. Friendly staff and nicely decorated rooms
Stayed 3 nights in Oct 2025

10/10 Excellent

Loren

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Cute room, kind staff, great location.
Stayed 3 nights in Sep 2025

10/10 Excellent

Gretchen

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

10/10 Excellent

Shai

Stayed 2 nights in Sep 2025

10/10 Excellent

Steve

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely hotel in Boston . Great welcoming and helpful staff and quirky, bright rooms . Great location - metro system nearby but we walked everywhere . Great bar and restaurant too
Stayed 3 nights in Sep 2025

10/10 Excellent

Kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff were great. Location was excellent. Bed was comfortable. Coffee machine worked. One lightbulb didn’t.
Stayed 3 nights in Oct 2025

6/10 Okay

Cara

Liked: Cleanliness, property conditions & facilities, room comfort
Disliked: Staff & service

Everything was great until…

Cleaned our room out before we checked out. Threw our stuff away that we had laid out to come back and get after breakfast. The desk even ask if we were leaving and we said no we were coming back after we ate
Stayed 1 night in Oct 2025

10/10 Excellent

KAREN

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
They gave us an early check-in without asking they provided really cute tin bottles of water with a pineapple logo. They also promote dog adoption, which is really great.
Stayed 2 nights in Sep 2025

10/10 Excellent

dana

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

6/10 Okay

Robert

Stayed 2 nights in Sep 2025

8/10 Good

Shaun

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Quirky little Hotel in a quiet residential area of South End. Reception staff were excellent, room was decked out in the Pineapple theme - very good. Bar on site - good but only used it once as we were here to explore. Back Bay T Station is 5 min walk & 3 stops to centre of Boston. I would recommend this hotel to anyone & everyone.
Stayed 5 nights in Sep 2025

10/10 Excellent

michelle

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this hotel!! Room only, very comfy bed and bedding - 2 duvets so you no longer have to fight for your half….. genius!!! Loved all of the little extras, silky robes, coffee maker with tea pods (I’m a tea drinker and so many places only supply coffee) free metal water bottle and fresh/chilled/gas water machine in the reception alongside free coffee all day. In the Back Bay Area which is super lovely and we walked from here into Boston which was about 20 mins and also back from Fenway Park after a game which was about 30-40 mins but was very safe. Also very close to the Avis/Budget garage when you need to collect the hire car!! Would highly recommend!
Stayed 3 nights in Sep 2025

10/10 Excellent

Jane E

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2025

10/10 Excellent

Tami

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
No photos sorry
Stayed 1 night in Sep 2025

8/10 Good

jacqueline

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Mitchell and Silvia were so extraordinary helpful nothing was too much trouble. The position was central and the rooms were fun ( touch of pineapples) and clean. Would highly recommend it as a less expensive place to stay
Stayed 3 nights in Sep 2025

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Sep 2025

2/10 Terrible

Richard

Traveled with partner
Disliked: Staff & service, amenities, property conditions & facilities
Hotel priced like a five star but rooms were the size of a closet with limited housekeeping. Our room was 60 degrees - freezing! When we asked for help to make the room warmer we were told management did not plan to turn the heat on for another week. They brought us a space heater that was loud and dangerous. We turned it off and nearly froze to death. We will never come back here at any price. Beware - the front desk did not have any concerns about our satisfaction.
Stayed 2 nights in Sep 2025

8/10 Good

steven louis

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent staff, incredible location for walking around town.
Stayed 3 nights in Sep 2025

8/10 Good

Christopher

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Sep 2025

6/10 Okay

Curtis

Traveled with family
Liked: Cleanliness, staff & service
Disliked: Amenities
Nice location. Rooms had no microwave or refrigerator. Leaky toilet was very loud, had to turn off water after each use. AC ran until too cold, needs thermostat adjustment.
Stayed 3 nights in Sep 2025

10/10 Excellent

Teresa

Stayed 1 night in Sep 2025

10/10 Excellent

Ashley

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The perfect location! Super comfy beds.
Stayed 2 nights in Sep 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
Very interesting hotel, very quiky but lovely room. Very clean. Awesome, helpful staff. Would highly recommend
Stayed 1 night in Sep 2025

10/10 Excellent

Hunter

Stayed 3 nights in Aug 2025

10/10 Excellent

Oliver

Stayed 1 night in Sep 2025