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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

Choose dates to view prices

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.
VIP Access

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Air conditioning
  • Bar
  • 24/7 front desk

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  • Experience top-rated quality and exceptional service
  • Get an in-stay perk at select properties, plus free room upgrades, early check-in, and late check-out when available

Room options

Available filters for rooms
Showing 2 of 2 rooms

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)

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
Down duvet
Premium bedding
Designer toiletries
Private bathroom
  • 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)

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
Down duvet
Premium bedding
Designer toiletries
Private bathroom
  • Sleeps 2
  • 1 King Bed

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Exterior

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Jan 28 - Jan 29
Total with taxes and fees
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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 guideOpens in a new window
Map
26 Chandler St, Boston, MA, 02116

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

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, concierge services, and smoke-free premises
  • An elevator, multilingual staff, and a water dispenser
  • Tour/ticket assistance, luggage storage, and coffee/tea in the lobby
  • 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

Similar properties

Exterior
Charlesmark Hotel
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
8.8 out of 10, Excellent, 1,129 reviews
$119 nightly
The price is $137
Jan 28 - Jan 29
Total with taxes and fees
Charlesmark Hotel

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

As of Jan 17, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Feb 1, 2026 start from $64.0, 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.

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 15-minute walk of Copley Square and Boston Common. Fenway Park and New England Aquarium 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. 624 out of 1001 reviews
Rating 8 - Good. 251 out of 1001 reviews
Rating 6 - Okay. 71 out of 1001 reviews
Rating 4 - Poor. 32 out of 1001 reviews
Rating 2 - Terrible. 23 out of 1001 reviews

Reviews

10/10 Excellent

Jan S

Liked: Cleanliness, amenities, property conditions & facilities
We've been to several Staypineapple hotels and they're always great. Clean rooms with comfortable beds and nice little extras that make the stay more pleasant.
Stayed 1 night in Jan 2026

10/10 Excellent

Jasmyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs!
Stayed 3 nights in Dec 2025

10/10 Excellent

Dandre

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was absolutely amazing and met all needs.
Stayed 2 nights in Jan 2026

10/10 Excellent

John

Liked: Cleanliness, property conditions & facilities
Small but well layed out room. Small bathroom but very functional. Room was up to sate and very clean. Staff very friendly and helpful. Nice bar area.
Bathroom
No closet but very creative storage.
Wall mounted wide screen
All rooms have Keurig coffee makers.
Stayed 2 nights in Dec 2025

10/10 Excellent

Kevin

Liked: Cleanliness, amenities, property conditions & facilities
In an extremely cute area - a short walk and you're in this beautiful neighborhood with great shops and food. The hotel staff were so incredibly nice. The room was very comfortable. The bathroom is a little small, but very clean and has a great shower. Would absolutely stay here again!
Stayed 4 nights in Jun 2025

10/10 Excellent

Loren

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

10/10 Excellent

Lauren

Liked: Cleanliness, amenities, property conditions & facilities
Room was lovely. Clean and well maintained. The front desk stay were very friendly and helpful. I will definitely stay there again !
Stayed 5 nights in Nov 2025

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

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

10/10 Excellent

Bianca

Liked: Cleanliness, amenities, property conditions & facilities
Previously stayed prior to it being changed to Staypineapple. Love the renovations and new look. Beds were comfy and completely dog friendly. Staff are friendly and helpful. Plan on staying there again. Enjoyed my stay.
Stayed 4 nights in Oct 2025

10/10 Excellent

Yamel

Liked: Cleanliness, amenities, property conditions & facilities
Staff courteous. Very pretty room!
Stayed 1 night in Nov 2025

10/10 Excellent

Steve

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

Ashley

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

10/10 Excellent

Cathy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast only available on weekends. Room clean but bathroom small. Nice helpful staff. Bar-good options. Dinner opens at 4pm. Great location
Stayed 3 nights in Oct 2025

10/10 Excellent

Randall

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Enjoyed the onsite bar and other amenities. Room was comfortable. Bathroom was very tiny, but manageable. Very walkable to shopping and dining options. Decor was very nice. Would recommend.
Stayed 4 nights 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

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

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

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

Jonathan

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

10/10 Excellent

Holly

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

Friendly Staff

Both the staff at the hotel and the Trophy Room restaurant were absolutely amazing!! Beds were very comfortable and we liked the location
Stayed 3 nights in Jun 2025

8/10 Good

Karen

Liked: Cleanliness, amenities
Great staff and great location, convenient to trains and subway. Fun bar in the lobby connected to the hotel. Very comfy beds.
Stayed 3 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

Caitlin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This hotel is so cute! It was a great location to everything!
Stayed 3 nights in Apr 2025

10/10 Excellent

Brigid

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