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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • Air conditioning

Explore the area

View in a map
26 Chandler St, Boston, MA, 02116
  • Place, Copley Square
    ‪8 min walk‬
  • Place, Boston Common
    ‪13 min walk‬
  • Place, Fenway Park
    ‪2 min drive‬
  • Airport, Boston, MA (BOS-Logan Intl.)
    ‪5 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 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
  • ‪Berkeley Perk Cafe - ‬1 min walk
  • ‪Trophy Room - ‬1 min walk
  • ‪Billy's Sub Shop - ‬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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Nov 23 - Nov 24
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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 Nov 12, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Nov 26, 2025 start from $104.72, 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.

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. 612 out of 1004 reviews
Rating 8 - Good. 261 out of 1004 reviews
Rating 6 - Okay. 72 out of 1004 reviews
Rating 4 - Poor. 35 out of 1004 reviews
Rating 2 - Terrible. 24 out of 1004 reviews

Reviews

10/10 Excellent

Thomas

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Aug 2025

10/10 Excellent

Clelia Maria

Liked: Cleanliness, staff & service, property conditions & facilities
Great location
Stayed 5 nights in Jul 2025

8/10 Good

James

Liked: Cleanliness, staff & service, room comfort

A good place to stay

A good hotel . Bit shabby round the edges, but all in all, great. Super friendly staff . Nice bar. Free coffee in reception and a coffee machine in the room. Handy enough for the city . A good vibe to the place
Stayed 2 nights in Aug 2025

10/10 Excellent

Francis

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

Great location hotel with great atmosphere

The room was...cozy. The hotel was had a great atmosphere, comfortable bed, and was walking distance to many restaurants and sights. Would highly recommend.
Stayed 2 nights in Jul 2025

10/10 Excellent

Mitchell

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was the single greatest stay of my life. The hotel is so cute and beautiful with lovely pineapple decor on the pillows, ceiling, and everywhere else (the attention to detail is superb) they offer you a complimentary drink upon check in, they provide you with a free metal recyclable water bottle, and a very comfortable and soft robe. However, The most important moment of my trip was the incredible house keeping staff! I was there to get married and couldn’t get dressed and leave until 3:30. Not only did the staff stay later to clean my room before I brought my bride back after the wedding, but they decorated the entire room with a sequined bed runner, balloons, confetti, decorations, and more. Every member of the front desk staff were so amazing and kind and helpful every step of the way! Thank you all so much from the bottom of my heart on behalf of myself and my bride!! She was so excited to enter the room and have one last wedding day surprise! We will be back (exclusively!) to the Pineapple! 🍍
Surprise decorations on our wedding night!
Surprise decorations on our wedding night!
Surprise decorations on our wedding night!
Stayed 3 nights in Aug 2025

10/10 Excellent

Duwayne

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2025

10/10 Excellent

Ken

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Jul 2025

10/10 Excellent

Mark

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Worked out really well from 3 days in Boston
Stayed 3 nights in Aug 2025

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, property conditions & facilities
Super cute boutique hotel, staff were incredibly friendly and helpful. Rooms were small but cozy, the separate duvets were a great touch. Would definitely return!
Stayed 3 nights in Jul 2025

8/10 Good

Michael

Liked: Cleanliness, staff & service, property conditions & facilities
nice place to stay but the bedding was odd
Stayed 2 nights in Jul 2025

4/10 Poor

Charles

Business traveler, Traveled with partner
Disliked: Amenities, property conditions & facilities
The bed not having a sheet was weird. Only a comforter to sleep with caused me to sweat through the night. The room was too small and the furniture odd. I got charged 25 dollars for "amenities" (hidden cost) and I don't know about you all, but I am sick of hidden costs. I will never stay at this hotel again.
Stayed 1 night in Jul 2025

2/10 Terrible

Verified traveler

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

Skip it.

The hotel was nice, clean, and a good value.We had a HUGE issue with payments. Four different employees lied about the charges. We are over- charged and refunded, charged again for items we were told would not be charged. I had to ask four times for a receipt. We experienced very shady business processes and communication.
Stayed 3 nights in Jul 2025

10/10 Excellent

Claudia

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay at the Staypineapple was great, the hotel was clean and quaint, the staff was friendly and welcoming. The property itself was easy to find and was close to the T train. The area was walkable and had alot of options for food and drinks. The room was beautiful and clean. We really enjoyed our stay
Stayed 5 nights in Jul 2025

10/10 Excellent

Gayle, Savannah

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a great little hotel.
Stayed 4 nights in Jul 2025

8/10 Good

Jack

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

A fun, friendly and comfortable hotel

A quirky hotel in a great location. Our bed was really comfortable and the staff were very friendly. It was nice to be given a refillable bottle on arrival that could be topped up with icy cold still or sparkling water in reception, along with two vouchers for further drinks from the fridge in reception. We had a fantastic stay!
Stayed 4 nights in Jul 2025

10/10 Excellent

Jonathan

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was nice and clean. In a nice and safe location.
Stayed 3 nights in Jul 2025

6/10 Okay

Christina

Stayed 2 nights in Jul 2025

4/10 Poor

Anne

Liked: Cleanliness
Disliked: Staff & service, property conditions & facilities
Although there are many very cute touches to this property and it was well cleaned but it was not in any way worth its high cost. Cold air blowed on us all night from the mini-split. The room felt VERY DAMP throughout the stay. There are no closets, upper sheet, and no counter in the bathroom. Two of the three front desk persons were not particularly friendly. Matter of fact we felt like a bother just to ask basic questions. The amnities fee is really ridiculous. The food service and bonus treats are not available until 4pm when one is likely out and about. The hair products were not good and to get ice one had to go down 6 floors and ask the front desk.
Stayed 3 nights in Jul 2025

10/10 Excellent

Alison

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was cute and quirky. Many extra touches. I wish the on-site bar/restaurant was open for lunch. But overall delightful!!
Stayed 2 nights in Jul 2025

10/10 Excellent

Rajesh

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great value for the price
Stayed 2 nights in Jul 2025

10/10 Excellent

Brigid

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It’s in a nice location and the hotel is really cute. Severe able to walk to our event at the Wang and felt safe. The staff was very nice and there was a cute dog in residence.
Stayed 1 night in Jun 2025

10/10 Excellent

Ronny

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

10/10 Excellent

Shannon

Traveled with group, Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very quaint, fun hotel. Staff was very friendly, accomodating, and helpful. The room was compact, but comfortable, very European design. The pineapple theme throughout was fantastic. The towels, linens, etc were great quality. I would definitely stay again.
Stayed 2 nights in Jul 2025

10/10 Excellent

Stephanie

Liked: Amenities, property conditions & facilities
Stayed 4 nights in May 2025

10/10 Excellent

Diane

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in Jul 2025