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Staypineapple, A Delightful Hotel, South End

3.0 star property
Hotel with a restaurant, 9-minute walk to Copley Square

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

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Air conditioning

Get more when you're a member

  • Save 15% or more on select VIP Access properties when you reach Silver tier or above
  • 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
Premium bedding
Down duvet
Designer toiletries
Bathrobes
Air conditioning
Down comforter
Hypo-allergenic bedding available
Pillowtop mattress
Bathrobes
Designer toiletries
  • 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
Premium bedding
Down duvet
Designer toiletries
Bathrobes
Air conditioning
Down comforter
Hypo-allergenic bedding available
Pillowtop mattress
Bathrobes
Designer toiletries
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Map
26 Chandler St, Boston, MA, 02116

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

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
  • A water dispenser, luggage storage, and coffee/tea in the lobby
  • Multilingual staff, an elevator, 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

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 Nov 9, 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on Nov 23, 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.

How much is parking at Staypineapple, A Delightful Hotel, South End?

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

8.8

Excellent

9.4

Cleanliness

9.0

Location

9.2

Staff & service

9.2

Eco-friendliness

8.8

Property conditions & facilities
Rating 10 - Excellent. 610 out of 1002 reviews
Rating 8 - Good. 261 out of 1002 reviews
Rating 6 - Okay. 72 out of 1002 reviews
Rating 4 - Poor. 35 out of 1002 reviews
Rating 2 - Terrible. 24 out of 1002 reviews

Reviews

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

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

8/10 Good

Hailey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was nice
Stayed 3 nights in Aug 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

10/10 Excellent

KAREN

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

Marybeth

Liked: Cleanliness, staff & service, property conditions & facilities
Room was cozy
Stayed 2 nights in Aug 2025

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved our stay here! The hotel is great & the bar was super fun! The location was great, an easy walk to wherever you want go!
Stayed 2 nights in May 2025

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic spot for the price, it was super clean and cute! Only downside is no parking, but there was plenty of spots near it to park at. 10/10 experience and staff was super nice
Stayed 1 night in Aug 2025

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fun hotel with unique decor. Would stay there again
Stayed 2 nights in May 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

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

8/10 Good

James

Liked: Cleanliness, staff & service
Disliked: Amenities, property conditions & facilities
Tiny toilet
Stayed 4 nights in Sep 2025

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, property conditions & facilities
Loved this quirky boutique hotel. It has great character, very clean, great walkable location. In south end - convenient to shopping and Fenway!
Stayed 1 night in Apr 2025

10/10 Excellent

Barbara

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely amazing bedding - very comfortable! We will definitely stay again - very walkable to the Boston Commons, shopping, restaurants and theater. Staff were very nice and personable. A wonderful stay.
Stayed 2 nights in May 2025

4/10 Poor

akemi

Liked: Cleanliness
Disliked: Staff & service, amenities, property conditions & facilities
It’s terrible that the hotel rate doesn’t include amenities. The quality of the amenities isn’t even that good, yet they don’t give you the option to refuse them. they’re forced to pay for amenities. Absolutely awful.
Stayed 2 nights in Oct 2025

10/10 Excellent

Kim

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

Cute and fun

This is a cute, fun hotel. It is in a great location. Also offers a restaurant and bar. I love the bedding.
Stayed 2 nights in May 2025

10/10 Excellent

Ryan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great location, friendly staff, and comfortable rooms. Yes, the rooms are smaller than average, but only if you're expecting American-style hotel rooms (which waste a lot of space). It was plenty spacious, and very comfortable.
Stayed 4 nights in May 2025

10/10 Excellent

Carl

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
The most comfortable hotel I’ve ever stayed in!
Stayed 4 nights in Feb 2025

10/10 Excellent

Alison

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

S

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Simple hotel walking distance from station. Friendly basic comfortable
Stayed 1 night in Apr 2025

10/10 Excellent

Amy

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

enjoyed this boutique hotel

As noted in descriptions the room was small but very well situated to be comfortable and functional. Amenities to meet the needs of a few days of travel, bright comfortable space, conveniently located.
Stayed 2 nights in Mar 2025

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful, quaint hotel. Very nice location in residential, walkable city neighborhood. Staff is very friendly and helpful. Nice bar in the lobby that was not too loud. Only complaint was a single cockroach that visited our bathroom.
Stayed 2 nights in May 2025

10/10 Excellent

Katherine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such helpful staff!! And great with dogs
Stayed 1 night in Apr 2025

10/10 Excellent

Lori

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
StayPineapple is a lovely quirky hotel located in downtown Boston. Very walkable with affordable dining options close by. The rooms are spic and span with modern upgrades and ever so comfortable beds. Plus, it is a phenomenal bargain in an expensive world.
Stayed 2 nights in Mar 2025

10/10 Excellent

Susana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exceedingly good! We are so impressed with the concept and attention to detail in service and comfort. We will definitely choose Staypineapple when available.
Stayed 2 nights in May 2025