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Staypineapple A Delightful Hotel South End

eee - (888) 323-5826
Staypineapple A Delightful Hotel South End, 26 Chandler Street, Boston, MA -(888) 323-5826
Area: Back Bay - Copley Square
(Map)
4.2
HOTEL RATING: 
VERY GOOD
4.2 out of 5 (1043 Ratings)
5.4 miles Roadrunner Boston
v14 mins driving
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The Spotlight on Staypineapple A Delightful Hotel South End

Chic Comfort in Boston’s South End

Modern European-style charm meets classic Boston character at Staypineapple A Delightful Hotel South End. Nestled in the historic South End neighborhood, this boutique property puts you within walking distance of Newbury Street, Back Bay, and a lineup of top-rated restaurants and attractions. With sleek rooms, walk-in marble showers, and thoughtful touches like iPod docks and free WiFi, it’s a stylish base for your concert night out—or recovery the next morning.

Why Concert-goers love it

Music fans love this hotel’s walkable location—you're just a short stroll from venues like the House of Blues and others around Back Bay. Despite the central spot, the vibe inside is quiet and relaxing, perfect after a high-energy night. Late check-out at 12:00 pm gives you time to sleep in, and the 24-hour front desk is a big plus for late arrivals post-show.

Who this Hotel is great for

  • Groups of friends looking for a central crash pad with easy access to bars and music venues
  • Solo travelers catching a big-name artist
  • Couples turning a concert into a romantic Boston weekend
  • Fans needing a quiet, stylish space to recharge
  • Budget-conscious music lovers who still want boutique flair

Food and Drink Options

While there’s no on-site restaurant, you’re surrounded by great eateries in the South End. Whether you're grabbing tacos at a local spot or indulging in late-night ramen, you won’t go hungry. Breakfast joints open late nearby are perfect for a slow morning after the show, and coffee lovers will appreciate the local cafés within a block or two.

Nightlife Options

No live music in-house, but you’re close to some of Boston’s best cocktail bars and lounges. From craft cocktails to cozy pubs, the South End and Back Bay put nightlife options within easy walking distance. It’s a great base to explore the scene before or after your concert.

What People Say

Guests rave about the hotel’s stylish design, spotless rooms, and friendly staff. The walkable location gets top marks, and many guests say it’s a hidden gem in a quiet but central spot. The comfortable beds and upscale bathrooms are also frequently praised—ideal for post-show recovery.

Areas for Improvement

The hotel doesn’t have a full-service restaurant or bar on-site, which some guests miss. And while the rooms are cozy and charming, they can feel a bit compact if you're traveling with a lot of gear. But for most concert-goers, the location and comfort make up for it.

The Bottom Line

This boutique gem offers style, quiet, and walkable convenience—a perfect stay for concert-goers exploring Boston’s music scene.
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1 room
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2 guests
Amenities View More
y
Free Internet
w
Non Smoking
r
Pets Allowed
x
Free Breakfast
j
Free Parking
u
Swimming Pool
E
Fitness Center
A
Business Center
B
Airport Shuttle
q
Accessible
Other Amenities
` Garden
` Air Conditioning
` Bar
` 24-Hour Front Desk
` Express Check-In/Check-Out
` Elevator
` Hair dryer
` Coffee/tea maker
` Children's playground
` bathrobes
` Fishing
` Karaoke
` Heating
` telephone
` alarm clock
` kitchenware
` Boating
` Concierge services
` Free Wi-Fi
` Off-Site parking
` Restaurant(s)
` Daily Housekeeping
` English
` Arabic
` French
` Spanish
` Non-Smoking Rooms Available
` Slippers
` taxi service
` Pub crawls
` Smoke alarms
` Fire extinguishers
` Guests can opt-out of daily cleaning service
` First aid kit available
` Cashless payment available
` Linens, towels and laundry washed in accordance with local authority guidelines
` Hand sanitizer in guest accommodation and key areas
` Invoices
` Sterilizing equipment
` Staff trained in safety protocol
` Free face masks
` Ticket services
` Contactless check-in/out
` Food delivery
` Audible alarm
` Complimentary drinking water
` Daily disinfection
` Ironing amenities
` Luggage storage & lockers
` Non-smoking property
` Room towels provided
` Separate shower/bathtub
` Spa services
` Toiletries provided
` Tour services
` TV & Movies/Shows
` Air conditioning in public area
` Heating in public area
` Desk/workspace available
` Allergy-free rooms available
` Cleaning products available
` Pets allowed (charges may apply)
` Alcoholic beverages available
` Bicycle rental (charges may apply)

Staypineapple A Delightful Hotel South End Guest Reviews

Overall Average Score: 
Very Good (4.2 out of 5)

Write a review

5

Exceptional - 5.0 out of 5

Andrew S, Boston, visiting Wilbur Theatre

Me and my girlfriend spent one night and were very pleased with our brief stay. Would definitely recommend the hotel to others, and if we found ourselves needing a place to stay in the Boston area would definitely stay at the Chandler Inn again.

Liked: Everything besides room temperature.
Disliked: Room was too hot - couldn't figure out how to turn the heat down.

3

Pleasant - 3.0 out of 5

Melissa, Providence, visiting Wilbur Theatre

Liked: Conveniently located; nicely decorated; cool bar downstairs.
Disliked: Bed was extremely uncomfortable.

1.5

Poor - 1.5 out of 5

Deborah Wed, 13 August 2025

Not going to stay at...

Liked: The location of the hotel was near our daughter so that was good. It is near downtown with lots of nice restaurants near by. The coffee shop around the corner "Berkeley Perk" was awesome! The restaurant attached to the hotel, The Trophy Room, had good cocktails and the food was good. The bed was comfortable and they have air conditioning.
Disliked: The bathroom was disgusting. It appeared updated with gray and white tile; however, the grout had turned yellow and looked like it had never been cleaned. The bathroom floor was slimy and they were parts were the grout was completely missing and black. It was really gross. They also charged a $25 amenities fee per day which was a joke. We still have no idea was that fee was paying for. The rooms are only serviced every other day. They advertise that they have treats in the lobby from 3pm - 5pm but the treats consist of a small plate with around 20 cookies on it. Most of the time, the cookies were completely gone by 3:15pm. The rooms are teeny tiny. If you are a big person, you would not be comfortable in the rooms.

5

Exceptional - 5.0 out of 5

Rebecca Tue, 12 August 2025

Exceptional

3.5

Good - 3.5 out of 5

Elizabeth Sun, 10 August 2025

Simple and comfy accommodations in...

Liked: Bedding is super comfortable. Love the complimentary drink. Location was great, close to a T-line. We didn’t stop by but we did see the bar below happening so it looked like it had a great social scene.
Disliked: For a short stay the small bathroom worked but for a longer stay they bathroom would have been too small to stand.

4

Very Good - 4.0 out of 5

Ellen Sat, 9 August 2025

Lovely stay

Liked: Good location Nice bar. N staff v helpful. Cosy rooms n robes.
Disliked: Amenity charge per person should just be part of room it looks like an extra charge.

5

Exceptional - 5.0 out of 5

Jeff Fri, 8 August 2025

A Delightful Hotel!

Liked: Its location was fantastic
Disliked: As many have written it’s a small room and bathroom. Having said that if you organize yourself correctly, it’s not a problem.

4

Very Good - 4.0 out of 5

Dominika Fri, 8 August 2025

Very good

4

Very Good - 4.0 out of 5

Ilesha Thu, 7 August 2025

We arrived after midnight and...

Liked: Very quiet, comfortable bed, flexible with later check out

4.5

Wonderful - 4.5 out of 5

Neil Sun, 3 August 2025

Superb

3

Pleasant - 3.0 out of 5

Susan Fri, 1 August 2025

Pleasant

Liked: Front desk staff was very welcoming. Bed was comfortable.
Disliked: Shower flooded bathroom. Temperature hard to control.

4

Very Good - 4.0 out of 5

Brooke Sat, 26 July 2025

Very good

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Staypineapple A Delightful Hotel South End 26 Chandler Street, Boston, MA