In the heart of South End, Staypineapple, A Delightful Hotel, South End offers a haven of relaxation. With a bar and restaurant on site, you can unwind with your favorite drink or meal. Explore the nearby Copley Place and Newbury Street on two wheels with free bicycle rentals or get insider tips from the multilingual staff.
Boston, MA (BNH-Boston Harbor Seaplane Base) - 17 min drive
Beverly, MA (BVY-Beverly Municipal) - 33 min drive
Norwood, MA (OWD-Norwood Memorial) - 35 min drive
Bedford, MA (BED-Laurence G. Hanscom Field) - 35 min drive
Lawrence, MA (LWM-Lawrence Municipal) - 36 min drive
Portsmouth, NH (PSM-Portsmouth Intl.) - 72 min drive
Back Bay Station - 6 min walk
South Station - 21 min walk
Boston Ruggles Station - 25 min walk
Arlington Station - 8 min walk
Tufts Medical Center Station - 9 min walk
Copley Station - 10 min walk
Restaurants
Club Cafe - 3 min walk
Grill 23 & Bar - 4 min walk
Billy's Sub Shop - 1 min walk
Greystone Cafe - 5 min walk
Clerys - 5 min walk
About this property
Staypineapple, A Delightful Hotel, South End
Staypineapple, A Delightful Hotel, South End puts you in a great location, within just a 10-minute walk of Copley Square and Copley Place. For a bite to eat, guests can check out Trophy Room, which serves American cuisine and is open for dinner. Other highlights at this boutique hotel include a bar/lounge and free bike rentals. Fellow travelers love the helpful staff and location. Public transportation is just a short walk: Arlington Station is 8 minutes and Tufts Medical Center Station is 9 minutes.
Languages
English, French, Spanish
At a glance
DONE
Hotel size
56 rooms
Arranged over 8 floors
DONE
Arriving/Leaving
Check-in start time: 4 PM; Check-in end time: midnight
Minimum check-in age: 18
Check-out time is noon
Contactless check-out available
DONE
Special check-in instructions
Front desk staff will greet guests on arrival at the property
DONE
Required at check-in
Credit card, debit card, or cash deposit required for incidental charges
Government-issued photo ID may be required
Minimum check-in age is 18
DONE
Children
No cribs (infant beds)
DONE
Pets
Pets allowed (dogs only, 2 total)*
Service animals welcome
Specific rooms only, restrictions apply*
Food and water bowls available
LOCAL_PARKING
Parking
No onsite parking
DONE
Other information
Smoke-free property
Property amenities
Food and drink
Restaurant
Bar/lounge
Coffee/tea in a common area
Services
24-hour front desk
Concierge services
Tour/ticket assistance
Luggage storage
Multilingual staff
Free bicycle rentals
Facilities
1 building/tower
Built in 1900
Accessibility
Elevator
Wheelchair-accessible path of travel
Wheelchair-accessible concierge desk
Wheelchair-accessible registration desk
Room amenities
Be entertained
IPod docking station
50-inch flat-screen TV
Satellite TV channels
Streaming services
Home comfort
Climate-controlled air conditioning and heating
Coffee/tea maker
Bathrobes
Iron/ironing board (on request)
Sleep well
Hypo-allergenic bedding
Down comforter
Premium bedding
Pillowtop mattress
Freshen up
Private bathroom
Shower only
Designer toiletries
Hair dryer
Towels
Stay connected
Desk
Free local calls
Food and drink
Free bottled water
More
Housekeeping (on request)
Special features
Dining
Trophy Room - This restaurant specializes in American cuisine and serves brunch and dinner. Guests can enjoy drinks at the bar.
Fees & policies
Mandatory fees
You'll be asked to pay the following charges by the property at check-in or check-out. Fees may include applicable taxes:
Resort fee: USD 29.06 per accommodation, per night
Resort fee inclusions:
Additional inclusions
In-room bottled water
In-room coffee
Internet access (may be limited)
Sporting facilities or equipment
Pets
Service animals exempt from fees
Pets are allowed for an extra charge of USD 29.95 per pet, per night
Policies
Guests can rest easy knowing there's a smoke detector on site.
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
This property accepts credit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover, Diners Club, Union Pay
Cashless transactions are available.
State tax ID - C0014880350
Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.
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
Does Staypineapple, A Delightful Hotel, South End offer free cancellation for a full refund?
Yes, Staypineapple, A Delightful Hotel, South End does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.
Are pets allowed at Staypineapple, A Delightful Hotel, South End?
Yes, dogs are welcome, with a limit of 2 total. There's a charge of USD 29.95 per pet, per night. Service animals are exempt from fees. Food and water bowls are available.
Is parking offered on site at Staypineapple, A Delightful Hotel, South End?
Sorry, there's no onsite parking at Staypineapple, A Delightful Hotel, South End.
What are the check-in and check-out times at Staypineapple, A Delightful Hotel, South End?
Check-in start time: 4 PM; Check-in end time: midnight. Check-out time is noon. Contactless check-out is available.
Is there an onsite casino at Staypineapple, A Delightful Hotel, South End?
No, this hotel doesn't have a casino, but Encore Boston Harbor (9-min drive) is nearby.
What is there to do at Staypineapple, A Delightful Hotel, South End and nearby?
Have fun during the warmer months with activities such as cycling.
Are there restaurants at or near Staypineapple, A Delightful Hotel, South End?
Yes, Trophy Room offers American cuisine.
What's the area around Staypineapple, A Delightful Hotel, South End like?
Staypineapple, A Delightful Hotel, South End is in South End, a short 7-minute drive from Logan International Airport (BOS) and 9 minutes' walk from Copley Square. Travelers say that the hotel is in a great location.
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Staypineapple, A Delightful Hotel, South End Reviews
Reviews
8.8
Excellent
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
9.4/10
Cleanliness
9.2/10
Staff & service
8.4/10
Amenities
8.8/10
Property conditions & facilities
9.2/10
Eco-friendliness
Popular mentions
Room
Service staff
Location
Bed
Restaurant
Bar
Bathroom
Shower
Parking
Amenities
What guests liked
The property's restaurant and nearby dining options were highly praised for their quality, variety, and convenience. (9 reviews)
The property has a welcoming and dog-friendly atmosphere with helpful staff and accessible pet access. (3 reviews)
From real guest reviews summarized by AI.
Reviews
10/10 Exceptional
Jun 30, 2025
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
Holly
Holly, 3-night trip
10/10 Exceptional
Jun 13, 2025
Food is great here... Rooms are super cute.
Cyndie
Cyndie, 6-night trip
8/10 Very good
Jul 2, 2025
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.
Brett
Brett, 4-night trip
10/10 Exceptional
Jun 12, 2025
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.
Alice
Alice, 5-night trip
10/10 Exceptional
May 28, 2025
Love it here!
Renee
Renee, 2-night trip
10/10 Exceptional
Jun 11, 2025
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.
Ryan
Ryan, 4-night trip
8/10 Very good
Jun 20, 2025
I was in town for a conference.
Simon
Simon, 4-night trip
10/10 Exceptional
Mar 2, 2025
Great stay!
Hayden
Hayden, 1-night trip
8/10 Very good
Jul 8, 2025
Not staying here again for the price.
Room was too small, and noisy next to the stairs.
Ron
Ron, 4-night trip
10/10 Exceptional
May 10, 2025
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.
Kim
Kim, 2-night trip
10/10 Exceptional
Jul 9, 2025
I was indeed delighted!
This place truly is delightful! The decor is charming, yellow accents and pineapple-y. The bedding is SO comfortable. I ended up not feeling well one day and didn’t mind staying in bed for half a day. The room was so cozy! The hotel doesn’t have a microwave or fridge for guests to use, either in rooms or communally, so be forewarned. The loaner bikes are a nice touch and come in handy for a quick ride along the River Charles.
Lisa
Lisa, 2-night trip
10/10 Exceptional
Apr 8, 2025
This was such a cute hotel! Perfect stay for a few days in Boston. It was in a nice neighborhood and close to transport to explore the city. I would recommend this hotel to anyone.
Domenic
Domenic, 3-night trip
10/10 Exceptional
Apr 24, 2025
This property was so cozy and the staff was so welcoming! It was also in a great area for the marathon! Super happy and would return
Jessika
Jessika, 5-night trip
10/10 Exceptional
Feb 23, 2025
Great hotel with a good location..Every staff member provided us and amazing service ;)))
Melany
10/10 Exceptional
Apr 30, 2025
Simple hotel walking distance from station. Friendly basic comfortable
S
S, 1-night trip
10/10 Exceptional
Apr 20, 2025
They have the nicest staff imaginable! The beds are incredibly comfy- I can’t wait to go back! I’m blown away!
samantha
samantha, 1-night trip
6/10 Good
May 15, 2025
The surrounding area was great, however,the room was as small as a shoe box! The service was friendly and helpful.
andrew
andrew, 2-night trip
10/10 Exceptional
Mar 31, 2025
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.
Amy
Amy, 2-night trip
10/10 Exceptional
Feb 20, 2025
This hotel was so cute! The staff was amazing everything was spotless, the bar and restaurant great.
KellyJo
KellyJo, 1-night trip
10/10 Exceptional
Jan 29, 2025
Love love such a cute hotel
Priscilla
Priscilla, 1-night trip
10/10 Exceptional
Jan 25, 2025
perfect stay, perfect welcome
Nathalie
Nathalie, 1-night trip
10/10 Exceptional
Apr 7, 2025
Such helpful staff!! And great with dogs
Katherine
Katherine, 1-night trip
10/10 Exceptional
Feb 25, 2025
The most comfortable hotel I’ve ever stayed in!
Carl
Carl, 4-night trip
10/10 Exceptional
Mar 29, 2025
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.
Lori
Lori, 2-night trip
10/10 Exceptional
Apr 9, 2025
Great location with easy access to fun walkable neighborhoods and mass transit.
Small rooms but as long as you know what to expect they’re entirely reasonable, with tasteful updates and nice amenities.