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Staypineapple, A Delightful Hotel, South End

3.0 star property
This charming South End boutique hotel blends warm hospitality with vibrant city energy, creating a perfect base for exploring Boston's historic neighborhoods

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Interior - Staypineapple, A Delightful Hotel, South End (Boston)
Premium bedding, down comforters, pillowtop beds, desk - Staypineapple, A Delightful Hotel, South End (Boston)
Lobby sitting area - Staypineapple, A Delightful Hotel, South End (Boston)
Reception - Staypineapple, A Delightful Hotel, South End (Boston)
Bar (on property) - Staypineapple, A Delightful Hotel, South End (Boston)
Staypineapple, A Delightful Hotel in South End offers a relaxing spot after exploring Boston. Enjoy the on-site bar and restaurant, free bike rentals to visit Copley Place and Newbury Street, and multilingual staff for local insights and authentic experiences.

Reviews

9.0 out of 10
Wonderful

Popular amenities

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

Room options

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
(9 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
(47 reviews)
  • Sleeps 2
  • 1 King Bed

About the neighborhood

Located in South End, a neighborhood in Boston, Staypineapple, A Delightful Hotel, South End is near the airport and near a metro station. Fenway Park and Faneuil Hall Marketplace are notable landmarks, and the area's natural beauty can be seen at Boston Common and Boston Harbor. Looking to enjoy an event or a game? See what's going on at TD Garden, or consider Encore Boston Harbor for a night out. Visit our Boston travel guide
Map
26 Chandler St, Boston, MA, 02116

What's nearby

  • Copley Square
    Copley Square
    6 min walk - 0.4 miles
  • Copley Place
    Copley Place
    6 min walk - 0.4 miles
  • Newbury Street
    Newbury Street
    8 min walk - 0.5 miles
  • Boston Common
    Boston Common
    10 min walk - 0.5 miles
  • Boston Marathon Finish Line
    Boston Marathon Finish Line
    10 min walk - 0.6 miles

Getting around

  • Back Bay Station
    7 min walk
  • Arlington Station
    8 min walk
  • Boston, MA (BNH-Boston Harbor Seaplane Base)
    16 min drive

Restaurants

  • The Friendly Toast
    4 min walk
  • Club Café
    4 min walk
  • Grill 23 & Bar
    4 min walk
  • Billy's Sub Shop
    1 min walk
  • The Banks Seafood and Steak
    6 min walk

About this property

Staypineapple, A Delightful Hotel, South End

Boutique hotel near Copley Square
Located close to Boston Common and Fenway Park, Staypineapple, A Delightful Hotel, South End provides a bar and a restaurant.
You'll also find perks like:
  • Free bicycle rentals, an elevator, and a water dispenser
  • Coffee/tea in the lobby, luggage storage, and smoke-free premises
  • Multilingual staff, tour/ticket assistance, and a 24-hour front desk
  • Guest reviews give top marks for the helpful staff and location
Room features
All 56 rooms offer comforts such as premium bedding and laptop-friendly workspaces, in addition to thoughtful touches like air conditioning and bathrobes. Guest reviews speak positively of the clean rooms at the property.
Extra amenities include:
  • Hypo-allergenic bedding, pillowtop mattresses, and down comforters
  • Bathrooms with designer toiletries and showers
  • 50-inch flat-screen TVs with streaming services and cable channels
  • Coffee/tea makers, heating, and housekeeping

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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
  • Water dispenser

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
  • No plastic water bottles
  • Smoking not allowed
  • Water dispenser usage encouraged

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
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 29.95 per pet, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Specific rooms only, restrictions apply; pet-friendly rooms can be requested by contacting the property at the number on the booking confirmation
Food and water bowls are available

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

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • 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 have included all charges provided to us by the property.

Optional extras

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

The above list may not be comprehensive. Fees and deposits may 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

We should mention

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 Staypineapple, A Delightful Hotel, South End pet-friendly?

Yes, this property allows dogs (limit 2 total). There's a fee of USD 29.95 per pet, per night. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

How much is parking?

This property doesn't offer parking.

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

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

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

Check-out is at noon.

Where is Staypineapple, A Delightful Hotel, South End located?

Located in South End, this boutique hotel is within a 10-minute walk of Copley Square and Boston Common. Boston University and Fenway Park are also within 2 mi (3 km). Arlington Station is 8 minutes by foot and Tufts Medical Center Station is 9 minutes.

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Reviews

Staypineapple, A Delightful Hotel, South End Reviews

9.0

Wonderful

9.4

Cleanliness

9.0

Location

9.2

Staff & service

8.8

Property conditions & facilities
Rating 10 - Excellent. 643 out of 1004 reviews
Rating 8 - Good. 237 out of 1004 reviews
Rating 6 - Okay. 69 out of 1004 reviews
Rating 4 - Poor. 31 out of 1004 reviews
Rating 2 - Terrible. 24 out of 1004 reviews

Reviews

Verified

10/10 Excellent

Mariana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Me encantó. Cómodo, bonito y con un gran servicio. El detalle de la botella de agua fue fantástico.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
nice hotel near back bay station
Stayed 1 night in Mar 2026
Verified

8/10 Good

Yuko

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great downtown location and affordable rates for budget travelers. The staff was great. The room (expesicially the barhtoom) was teeny-tiny.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Matthew

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and comfortable room. Smaller, but comfortable. Bed was very cozy and loved the robes. Good location we walked everywhere. Quite noisy at night from traffic outside. But would definitely stay again.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean. Friendly and helpful staffs. Free water bottle.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Megan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The best!
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Shuheng

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
24h water supply with welcome drink. Exactly what I need
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely rooms, charming space, convenient to attractions.
Stayed 2 nights in Feb 2026
Verified

2/10 Terrible

Krystal

Disliked: Amenities, property conditions & facilities
We were coming from out of town. Checking in was fine. When we checked into our room it was 80 DEGREES!!! Turns out the heat was on. Air conditioning wasn't working. When we called the front desk, they said they completely shut off the AC during the winter and that we should open a window to have some breeze. We tried to open the window and the window was broken and wouldn't lock in place. The hallway and the bathroom were a reasonable temperature so we found it hard to believe that the AC was turned off. Unfortunately we believe the AC was broken and the heat was the only thing working. (Side note: the window shades had multiple rips and tears, definitely something that should be replaced.) My Husband and I could not stay under those conditions, we also believe that no other customer should be staying in a room that was 80 degrees. We left 10-15 minutes within being in the room. We did not receive any type of compensation for somewhere we didn't stay. We decided to stay at THE GODFREY HOTEL. Which we have stayed prior and it was AMAZING. When we told them about our experience with pineapple they upgraded our room! So if your looking for an amazing room with working air conditioning I would recommend The Godfrey hotel downtown Boston. The best staff and experience. Expedia only gave us a $20 credit.....
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Janina

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The beds were incredibly comfortable. We loved the individual duvets. The decor and ambiance were amazing. The staff was kind. The snack pack upgrade was very disappointing and sparse vs the picture. However, the overall experience was memorable.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Neil

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Thoroughly enjoyed my stay here. Excellent value.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

vasilios

Liked: Cleanliness, staff & service, property conditions & facilities
Making Pineapples Great Again
Stayed 1 night in Mar 2026
Verified

6/10 Okay

Taisha

Disliked: Cleanliness
Nice area and the staff were really nice but when we checked the room the sheets had stains and so did the towels & robe.
Stayed 1 night in Feb 2026
Verified

6/10 Okay

moonshine

Liked: Cleanliness, amenities, property conditions & facilities
There’s doesn’t seem to be any soundproofing I got stuck with noisy neighbors unfortunately otherwise the front desk staff was very friendly and informative
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Simeng

Liked: Cleanliness, property conditions & facilities
the staff is excellent!
Stayed 3 nights in Feb 2026
Verified

6/10 Okay

Jesse

Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
Charged a $29 amenity fee that was not disclosed when I checked in. Heat was on way too high with no way to control it. The bathroom sink is tiny. I also did not appreciate when the man who checked me in made a remark how my name sounded like a martial arts movie star (I’m Chinese). I come to Boston frequently and have stayed at many local hotels and would not stay here again.
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Joy

Liked: Cleanliness, amenities, property conditions & facilities
Loved this hotel. Convenient to everything, nice staff , rooms had everything you could need and the bed was very cozy. Loved the free reusable water bottle and the complimentary cocktail at the bar . Highly recommend
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Edna

Liked: Cleanliness, amenities, property conditions & facilities
Personal muy amable, muy buena ubicación y el cuarto muy bonito pensado en cada detalle
Stayed 3 nights in Jan 2026
Verified

8/10 Good

Mikita

Liked: Cleanliness, amenities, property conditions & facilities
Room was spotless but would be nice if they offer extra bottles of water
Stayed 5 nights in Jan 2026
Verified

10/10 Excellent

Skyler

Liked: Cleanliness, amenities, property conditions & facilities
Everyone was very kind and accommodating! Rooms were so cozy and clean. Would definitely stay again.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Fernando

Wonderful stay
Stayed 1 night in Jan 2026
Verified

8/10 Good

Bianca

Liked: Cleanliness, amenities, property conditions & facilities
Comodidades bem antigas mas nada que atrapalhe o uso, a recepção no quarto é bem bacana. Há um bar logo no térreo ao lado da recepção que não vi nos outros comentários e avaliações, porém a vedação do som é muita boa e não ouvimos nada, inclusive recebemos um vale bebida cada um! Recomendo para estadias curtas!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Aimee

Liked: Cleanliness, amenities, property conditions & facilities
Super cute room staff was great
Stayed 1 night in Jan 2026
Verified

8/10 Good

Lisa

Liked: Cleanliness, amenities, property conditions & facilities
Excellent customer service, free water/seltzer for water bottles, bar connected to hotel with great breakfast (weekend only), adorable room decor, comfy bed, nice size tv, small keurig inside room and staff let my daughter & I stay in lobby area until time to leave for airport. The only reason I gave 4 stars is bc the size of the bathroom. Stand-up shower plus spa shower head was lovely, but overall very small space. Tiny sink and def can’t have 2 ppl in space at one time except if 1 person in shower. Please don’t let that deter you from staying at hotel because it’s lovely. There is a $25 daily resort fee, make sure you set that side if on a budget. Back Bay T stop abt 8 min walk super close & 15 min from Prudential Center shopping. Thank you for wonderful stay!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Jan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We always enjoy the Staypineapple experience. Nice room, comfortable, clean and great service. Good location only a few minute walk to the Metro.
Stayed 1 night in Jan 2026