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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)
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)
Premium bedding, down comforters, pillowtop beds, desk - 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

  • 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)
  • 18 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Back Bay King

Premium bedding, down comforters, pillowtop beds, desk

Back Bay King

9.2 out of 10
Wonderful
(49 reviews)
  • 18 sq m
  • 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. Faneuil Hall Marketplace and Fenway Park 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
  • Newbury Street
    Newbury Street
    8 min walk - 0.5 miles
  • Copley Place
    Copley Place
    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
  • Grill 23 & Bar
    4 min walk
  • Flour Bakery + Cafe
    5 min walk
  • Club Café
    4 min walk
  • The Banks Seafood and Steak
    6 min walk

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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
  • Hardwood flooring in room
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible concierge desk
  • Wheelchair-accessible path of travel
  • Wheelchair-accessible registration desk
  • Wheelchair-accessible restaurant

More

  • 1 building
  • 8 floors
  • Built in 1900
  • Fireplace in lobby
  • 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
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • 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)

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.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Staypineapple, A Delightful Hotel, South End Reviews

9.0

Wonderful

9.4

Cleanliness

8.8

Location

9.2

Staff & service

8.8

Property conditions & facilities
Rating 10 - Excellent. 655 out of 1016 reviews
Rating 8 - Good. 231 out of 1016 reviews
Rating 6 - Okay. 71 out of 1016 reviews
Rating 4 - Poor. 32 out of 1016 reviews
Rating 2 - Terrible. 27 out of 1016 reviews

Reviews

Verified

10/10 Excellent

Karina

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good location, great staff, clean rooms
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Laura

Liked: Cleanliness
Accommodations and staff were above what I expected. Will absolutely be back.
Stayed 1 night in Apr 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

Hortencia

Liked: Cleanliness, staff & service, amenities
Clean and great location. Wonderful service. Really enjoyed our stay and will return.
Stayed 3 nights in Nov 2025
Verified

8/10 Good

Debora

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I like this property. Fantastic location for this solo female traveler and the staff is super friendly. The room was small (expected in a historic space) so there was no place to sit other than the bed and no other furniture. Even leaving my suitcase open during my 3 night stay was a challenge in the small room’s foot print. What I really liked was the vibe and the amenities such a free refillable water bottle, real glasses and coffee cups in the room, and a bathrobe.
Stayed 3 nights in Apr 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

Robert

Liked: Cleanliness, staff & service, amenities
The cleanliness of the entire property was above average, the friendliness was fantastic
Stayed 1 night in Feb 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

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

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

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

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

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
Verified

10/10 Excellent

waileong

Liked: Cleanliness, staff & service, amenities
staff and room are great
Stayed 2 nights in Jan 2026
Verified

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
Verified

10/10 Excellent

vasilios

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

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
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

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
Verified

10/10 Excellent

Theresa

Liked: Cleanliness, staff & service, amenities
clean, cute, great location, parking garage minutes away
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Loren

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

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
Verified

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
Verified

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
Verified

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