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Staypineapple, A Delightful Hotel, South End

3.0 star property
3-star boutique hotel near Copley Square

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

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

9.0 out of 10
Wonderful
(37 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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4.4 out of 5, Excellent, 2,095 reviews
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Total includes 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

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.

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. 568 out of 965 reviews
Rating 8 - Good. 268 out of 965 reviews
Rating 6 - Okay. 73 out of 965 reviews
Rating 4 - Poor. 34 out of 965 reviews
Rating 2 - Terrible. 22 out of 965 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

6/10 Okay

STEPHEN, AMSTON

Stayed 2 nights in Jun 2025

10/10 Excellent

Gina, KANSAS CITY

Stayed 4 nights in Jun 2025

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

Jessika

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property was so cozy and the staff was so welcoming! It was also in a great area for the marathon! Super happy and would return
Stayed 5 nights in Apr 2025

10/10 Excellent

Alison

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 3 nights in Apr 2025

10/10 Excellent

Al

Liked: Cleanliness, staff & service, property conditions & facilities
Clean room with everything you need. Very affordable considering the great location.
Stayed 3 nights in Apr 2025

10/10 Excellent

Andrea E

Stayed 4 nights in Feb 2025

10/10 Excellent

Megan

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

10/10 Excellent

samantha

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
They have the nicest staff imaginable! The beds are incredibly comfy- I can’t wait to go back! I’m blown away!
Stayed 1 night in Apr 2025

10/10 Excellent

Roseanne, Whitestone

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Apr 2025

10/10 Excellent

Verified traveler

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

Small but comfortable

Although the room was quite tight, could have used a chair, and the sink in the batjroom was too small, but very clean and comfortable otherwise.
Stayed 3 nights in Apr 2025

10/10 Excellent

Heather

Stayed 1 night in Mar 2025

2/10 Terrible

Karla

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities
We had no heat in our room the first night and it was 28 degrees outside. The clerk gave us his space heater to keep warm. The rooms are too small to move around - no closet, no counter space in the bathroom - I would suggest another hotel
Stayed 3 nights in Apr 2025

10/10 Excellent

Wesley

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
The staff was very friendly. The location was perfect for exploring the city. The bed was beyond comfortable.
Stayed 3 nights in Apr 2025

10/10 Excellent

Kelly

Stayed 2 nights in Mar 2025

8/10 Good

Madeline

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I love StayPinapple because they wash their comforters after every guest stay (yes if you didn’t know, other hotels don’t - gross). It may not be the most environmentally conscious but I personally would sacrifice that in this case and know that I’m sleeping in a perfectly clean bed with no strangers germs in it. They also give you a free water in your room (amazing - why don’t all hotels do this) and a free “chip” at check in that you can trade in for another drink or a snack. The room was very clean overall. The hotel is in a very residential area so it’s not that accessible to things location wise, but the upside to that is that it was very quiet for a hotel in a city, no traffic noises etc keeping you up at night. It is a dog friendly hotel and I did hear a few dogs barking throughout the night. You could tell the owners tried to keep them as quiet as possible though. It didn’t really bother me, it kind of made it feel homey actually because I have three dogs at home. Just something to note though if you plan on staying here. My only “big” complaint is there is not parking anywhere near the hotel, I had to walk several blocks. Which is annoying when you have a suitcase and Boston has cobblestone everything you make a big ruckus going getting from the parking garage to the hotel. And also annoying when it’s bad weather. I know they can’t make parking appear but maybe there could be a system with curbside drop off of luggage then go park your car. Overall really great hotel
Stayed 1 night in Apr 2025

8/10 Good

Jennifer

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved this hotel. The location was great and was walking distance from a metro station. The room was clean and perfect for what it was needed for. Restroom was on the smaller size but didn’t affect us. There was a restaurant/bar downstairs where we got a drink. Friendly staff and cute pups! I would stay here again.
Stayed 4 nights in Apr 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