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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Air conditioning
The current price is NZ$556
includes taxes & fees
30 Oct - 31 Oct

Explore the area

View 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 Back Bay King

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

Back Bay King

9.0 out of 10
Wonderful
(46 reviews)

Highlights

Air conditioning
Flat-screen TV
Hypo-allergenic bedding
Down duvet
Pillow-top bed
Premium bedding
Hairdryer
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

8.6 out of 10
Excellent
(8 reviews)

Highlights

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

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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
  • ‪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

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.

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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 30 Sept 2025, prices found for a 1-night stay for 2 adults at Staypineapple, A Delightful Hotel, South End on 30 Oct 2025 start from NZ$505.45, 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. 610 out of 1019 reviews
Rating 8 - Good. 275 out of 1019 reviews
Rating 6 - Okay. 74 out of 1019 reviews
Rating 4 - Poor. 36 out of 1019 reviews
Rating 2 - Terrible. 24 out of 1019 reviews

9.4/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

8/10 Good

Brett

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

Great time in the south end

We had a great stay at Staypineapple Boston! The staff was truly amazing—friendly, helpful, and made us feel very welcome. The location is fantastic, perfect for exploring the city. A couple of small issues like holes in the blinds and some city noise at night, but overall, a really enjoyable experience.
Stayed 4 nights in Jun 2025

6/10 Okay

STEPHEN, AMSTON

Stayed 2 nights in Jun 2025

10/10 Excellent

Holly

Stayed 4 nights in Jun 2025

8/10 Good

Walter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great option within walking distance to downtown
Stayed 3 nights in Jun 2025

8/10 Good

Michael

Liked: Staff & service, room comfort
Stayed 1 night in Jun 2025

10/10 Excellent

Holly

Travelled with family
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

4/10 Poor

Douglas

Stayed 1 night in Jun 2025

8/10 Good

Jade

Business traveller
Liked: Cleanliness, staff & service, amenities
Super nice staff! Like the free water bottle for fill ups. Like the area / food abundant. But room super small and lots of noise from street and thin windows/walls.
Stayed 4 nights in Jun 2025

8/10 Good

Simon

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
I was in town for a conference.
Stayed 4 nights in Jun 2025

10/10 Excellent

Carrie

Business traveller, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
had a wonderful experience. Very cozy and comfortable love the ambience like The Restaurant was attached to it totally recommend.
Stayed 4 nights in May 2025

10/10 Excellent

Mary

Travelled with partner, Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Small room but they make the most of the space. Beds, pillows, linens, and towels comfortable. A/C is low noise. Hotel is on a culdesac so street noise is minimal, but did here the train once. Windows are not very sound proof, but didn't hear room neighbors. Close to many great restaurants, coffee and 7-11. Subway about a 12 minute walk. But walk is over cobblestone so beware of rolling luggage. Staff was friendly and helpful. Bar was handy, but didn't eat at the grill. Would recommend and stay here again.
Stayed 4 nights in Jun 2025

8/10 Good

Kelly

Liked: Cleanliness, staff & service, property conditions & facilities
I stayed for 13 nights. Very friendly front desk staff, loved the bedding, location was great (a few blocks from Back Bay subway stop). The water bar was helpful, morning coffee always good, and loved the afternoon cookies. A dry cleaner right across the street that does wash and fold. Also great if you need a late check out (noon). The negatives- TINY rooms, no mini fridge/microwave, and shower had poor water pressure. Overall, a good stay at a good value- this was one of the more reasonably priced hotels. I would stay again!
Stayed 12 nights in Jun 2025

8/10 Good

Fullando

Liked: Cleanliness, staff & service, amenities
This is very cute hotel nestled in a quiet residential area next to everything.
Stayed 3 nights in Jun 2025

10/10 Excellent

Gina, KANSAS CITY

Stayed 4 nights in Jun 2025

10/10 Excellent

Cyndie

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Food is great here... Rooms are super cute.
Stayed 6 nights in Jun 2025

8/10 Good

Chris

Liked: Cleanliness, property conditions & facilities
Stayed 3 nights in Jun 2025

10/10 Excellent

Raven

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My first Staypineapple hotel and now I’m in love!
Stayed 3 nights in May 2025

10/10 Excellent

Alice

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great little hotel. Friendly, front desk service. Great location to walk to all the sights. Clean and comfy. Small but perfect for a couples stay.
Stayed 5 nights in Jun 2025

8/10 Good

DAVID

Stayed 3 nights in Jun 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

shiva

Liked: Cleanliness, property conditions & facilities
Stayed 2 nights in Jun 2025

8/10 Good

Namthip

Travelled with family, Business traveller
Liked: Cleanliness, amenities
Stayed 3 nights in May 2025

10/10 Excellent

Violeta

Travelled with partner, Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Very cute room, stayed a couple nights and everything was pleasant. Close to many good restaurants and cafes. Staff was excellent. I would recommend to a single or couple, short walk to the train and bus lines. Bring your water bottle, they have a refill station in the lobby.
Stayed 4 nights in Jun 2025

10/10 Excellent

Hector

Stayed 2 nights in Jun 2025

10/10 Excellent

Federica

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Jun 2025