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Staypineapple, A Delightful Hotel, South End

3.0 star property
Hotel with a restaurant, a quick walk to Copley Square

Photo gallery for Staypineapple, A Delightful Hotel, South End

Interior
Lobby sitting area
Premium bedding, down duvets, pillow-top beds, desk
Reception
Bar (on property)

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Pet-friendly
  • Air conditioning
  • Restaurant
The current price is AU$458
includes taxes & fees
1 Sept - 2 Sept

Explore the area

View 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 duvets, pillow-top beds, desk

Back Bay King

9.0 out of 10
Wonderful
(42 reviews)

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Premium bedding
Pillow-top bed
Down duvet
Bathrobes
Designer toiletries
  • Sleeps 2
  • 1 King Bed

View all photos for South End Corner King

Premium bedding, down duvets, pillow-top beds, desk

South End Corner King

8.4 out of 10
Very good
(7 reviews)

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Premium bedding
Pillow-top bed
Down duvet
Bathrobes
Designer toiletries
  • Sleeps 2
  • 1 King Bed

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Exterior

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The price is AU$484
includes taxes & fees
1 Sept - 2 Sept
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About the area

Boston

Staypineapple, A Delightful Hotel, South End places you in the centre of Boston, within just a 15-minute stroll of Copley Square and Boston Common. Highlights at this boutique hotel include a restaurant and a bar/lounge. .The restaurant, Trophy Room, serves American cuisine and is open for brunch and dinner. Other amenities include coffee/tea in a common area and free use of bicycles. Bring your pet along and take advantage of this property's pet-friendly amenities, such as food and water bowls. .With a stay at this 3-property class South End hotel, you'll be 2.5 km (1.5 mi) from Fenway Park and 2.6 km (1.6 mi) from New England Aquarium.

What's nearby

  • Copley Square - 8 min walk - 0.7 km
  • Boston Common - 13 min walk - 1.1 km
  • Fenway Park - 2 min drive - 2.2 km
  • New England Aquarium - 2 min drive - 2.2 km
  • TD Garden - 4 min drive - 3.6 km

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
  • ‪Billy's Sub Shop - ‬1 min walk
  • ‪Trophy Room - ‬1 min walk
  • ‪Berkeley Perk Cafe - ‬1 min walk

About this property

Staypineapple, A Delightful Hotel, South End

Hotel with a restaurant, a quick walk to 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 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 members are multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Lift
  • No smoking on site
  • Bar or lounge
  • Dining venue
Staypineapple, A Delightful Hotel, South End offers 56 accommodations with iPod docking stations and complimentary bottles of water. Pillowtop beds feature down duvets and premium bedding. 50-inch flat-screen televisions come with satellite channels.

Bathrooms include a shower, bathrobes, designer toiletries and complimentary toiletries. Business-friendly amenities include desks and telephones; free local calls are provided (restrictions may apply). Additionally, rooms include coffee/tea makers and a hairdryer. Hypo-allergenic bedding and an iron/ironing board can be requested. Housekeeping is provided on request.

Languages

English, French, Spanish

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Property amenities

Internet

  • Available in all rooms: Free internet

Parking and transport

  • No on-site 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

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.
  • Lift
  • 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
  • Smoke-free property

Room amenities

Bedroom

  • Down comforter
  • Hypo-allergenic bedding
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Designer toiletries
  • Dressing gowns
  • 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

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.
  • Cots (infant beds) are not available.

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 on-site 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 all 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

What is the cancellation policy at Staypineapple, A Delightful Hotel, South End?

Staypineapple, A Delightful Hotel, South End offers free cancellation on select room rates. Check out the cancellation policy for more info.

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

As of 21 Aug 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on 1 Sept 2025 start from AU$413.15, including 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.

Are there any beaches close to Staypineapple, A Delightful Hotel, South End?

Yep, Staypineapple, A Delightful Hotel, South End is a short 8-minute walk from Carson Beach.

What makes Staypineapple, A Delightful Hotel, South End a romantic place to stay?

A lounge bar, plus pillowtop beds in the guestrooms, help set the scene for a romantic weekend at Staypineapple, A Delightful Hotel, South End.

Is there a free airport shuttle available at Staypineapple, A Delightful Hotel, South End?

No, Staypineapple, A Delightful Hotel, South End does not offer an airport shuttle service.

Is there a bar or restaurant at Staypineapple, A Delightful Hotel, South End?

Yep, they've got a lounge bar and an onsite restaurant that serves American cuisine. Pre dinner cocktails anyone?

What time are check-in & check-out at Staypineapple, A Delightful Hotel, South End?

Check-in begins at 4 PM. Check-out time is noon.

Are pets allowed at Staypineapple, A Delightful Hotel, South End?

Dogs are welcome at Staypineapple, A Delightful Hotel, South End, with food and water bowls on offer. Just so you know, there's a limit of 2 pets.

Staypineapple, A Delightful Hotel, South End Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 593 out of 999 reviews
Rating 8 - Good. 272 out of 999 reviews
Rating 6 - Okay. 75 out of 999 reviews
Rating 4 - Poor. 36 out of 999 reviews
Rating 2 - Terrible. 23 out of 999 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.6/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

2/10 Terrible

Xiaohang

Disliked: Cleanliness
Very awful and unsafe place :(
Stayed 2 nights in May 2025

8/10 Good

Sue, SPRINGFIELD

Travelled 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

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

Susana

Travelled with partner
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

8/10 Good

Brian

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
The rooms are small, but very clean and comfortable.
Stayed 1 night in May 2025

6/10 Okay

Sherryl

Travelled with family
Liked: Cleanliness, staff & service
Cute, eclectic hotel, however it's geared more for one person per room than two. A little tight and no place to put things. For me personally, I thought the price was a little high for the offering and amenities, especially when we got there and found out there was another $87 charge for amenities(?). It's an older hotel with some things in the room still needing update. The staff I encountered were very nice and helpful. A single person probably would find it suitable, but I would look for a different hotel if visiting the city again.
Stayed 3 nights in May 2025

10/10 Excellent

Vivek

Stayed 2 nights in May 2025

6/10 Okay

Jon

Liked: Cleanliness, property conditions & facilities, room comfort

Would consider Pineapple chain in future

Overall it’s a nice boutique hotel and a good location for walking and transportation. The single biggest issue is with “resort fees” while this was refunded this time, it’s such a stain on the overall experience. If you are required to pay it, it should show in the total price initially.
Stayed 3 nights in Mar 2025

10/10 Excellent

Jim

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Very central
Stayed 5 nights in May 2025

6/10 Okay

andrew

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities, room comfort
The surrounding area was great, however,the room was as small as a shoe box! The service was friendly and helpful.
Stayed 2 nights in May 2025

10/10 Excellent

Caitlin

Travelled with partner
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

2/10 Terrible

James

Stayed 4 nights in May 2025

8/10 Good

MARK

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

The definition of funky

Right after cool, offbeat, quirky, and unconventional in the list of synonyms for “funky” there should be a picture of the Staypineapple in Boston.
Stayed 1 night in May 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

Barbara

Travelled with family
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

6/10 Okay

Verified traveller

Liked: Cleanliness

Disappointed

Wanted to give it the benefit of the doubt since I went in knowing the rooms are small etc. The bathroom was EXTREMELY small though- hard to even wash your face in the sink. The biggest irritation was a daily $25 amenities fee for things that really should already be included- water bottle refills, in room coffee, wifi. It might be worth it if you plan to use the bikes? Otherwise it felt like a scam. Also the coffee cups weren’t cleaned on the every other day room cleaning & coffee wasn’t replaced either.
Stayed 4 nights in Apr 2025

10/10 Excellent

Mario

Business traveller
Liked: Staff & service, amenities
"Housekeeping only came every other day. However, the hotel and the service are good—well located and everyone is friendly. It's expensive, but I think it's one of the best options compared to other hotels."
Stayed 4 nights in May 2025

6/10 Okay

Allan

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

Say as it is

It’s a budget hotel and you get what you pay for. Staff cordially friendly. Room small, with nowhere to sit. Limited TV services and open to everyone WIFI. Reasonably placed to get into the Boston tourist area, approx a mile walk. Noisy as close to a freeway and train station (there again Boston is a noisy city)
Stayed 3 nights in May 2025

10/10 Excellent

Robert

Travelled with partner
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

Andrea

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the decor and the bikes to ride around the city!
Stayed 1 night in May 2025

8/10 Good

Cheryl

Liked: Cleanliness, property conditions & facilities, room comfort
Stayed 1 night in Apr 2025

10/10 Excellent

Helen

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very kind staff. Awesome bar connected and great food. Would stay again!
Stayed 1 night in Apr 2025

8/10 Good

Helen

Stayed 2 nights in Apr 2025

10/10 Excellent

S

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

8/10 Good

Verified traveller

Liked: Room comfort

Location is best thing

Check in was messy. Nobody seemed to know how to do it. Finally got to room. No wifi and no reply from hotel about how to resolve. Safe was locked and, again, no reply from hotel how to change. Location good, but overall service not great. Shame. Bar downstairs offers distinctly average drinks at prices more than other local bars. Worst espresso martini ($15, plus a 20% tip expected!!) I’ve ever had!
Stayed 2 nights in Apr 2025