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4-Star hotel

Staypineapple, A Delightful Hotel, South End

26 Chandler Street, BostonSee map

Good

1551 reviews

8.5/10

Stay highlights

Vibrant South End scene

Nestled in Boston's charming South End, Staypineapple offers easy access to trendy restaurants, art galleries, and beautiful parks, perfect for exploring the city's vibrant culture.

Pineapple perks galore

Indulge in unique experiences like complimentary pineapple-infused treats and personalized service that make every stay feel special and memorable.

Charming boutique style

Enjoy cozy accommodations with playful decor, featuring plush bedding and modern amenities, ensuring a delightful retreat after a day of adventure.

Popular amenities

Non-smoking rooms

Air conditioning

Restaurant

Pets allowed

Lift / Elevator

Luggage storage

Non-smoking throughout

Concierge service

Pet bowls

Pet basket

Staff adhere to local safety protocols

Guest rooms disinfected between stays

Cleaning standards that are effective against Coronavirus

Hand sanitizer in guest room and key areas

Cashless payment available

Fire extinguishers

First aid kit available

Sanitized tableware & silverware

Choose your room

Aug 28th – 29th 2026

1 Room, 2 Travellers

8.5

1551 reviews

Cleanliness

8.14

Services

9.11

Comfort

7.6

Amenities

8.63

Value

9.09

Location

8.65

Food

8.14

1985smn

Family · October 2025

10/10

Staypineapple was a really cute, boutique style hotel. I spent six days here and enjoyed my time! It was partly solo and then my cousin joined later on. We each had our own room next door to each othe...Staypineapple was a really cute, boutique style hotel. I spent six days here and enjoyed my time! It was partly solo and then my cousin joined later on. We each had our own room next door to each other. I really appreciated the staff making accommodations for my cousin to have a room next door considering we checked in days apart. I enjoyed having a reusable water bottle and then access to water 24/7 in the lobby. I tried the pineapple teriyaki wings and they were really good. The rooms are super small, BUT you know that when you look up the hotel. It’s perfect for solo travelers but I don’t know couples or friends would enjoy the space. The shower has a half door. I don’t like when hotels just don’t give a full door to a shower or curtains. But it wasn’t a big deal to mark them down. It is within walking distance (5-20 minutes) of food places and things to do. The Back Bay Orange line is also about a 5 minute walk. Logan airport is about an 11 minute Lyft ride or so without traffic. Staff was friendly. I felt safe in the area it’s located in. I would definitely stay here again.Show More

chrin22

Couples · October 2025

10/10

Overall it was a very good hotel stay at a reasonable price compared to other hotels in the area. It was within easy walking distance of Boston Commons, We enjoyed the ability to check out bicycles to...Overall it was a very good hotel stay at a reasonable price compared to other hotels in the area. It was within easy walking distance of Boston Commons, We enjoyed the ability to check out bicycles to go see local sights, and on the one day we walked to Beacon Hill there was a good steady rain, so the ability to check out umbrellas was very helpful. When our departing flight was delayed the front desk was able to accommodate a late checkout. The Saturday night traffic noise was a medium volume, but it died down before it got too late and we didn't notice any real traffic noise on Sunday morning or even on weekday mornings. We got a corner room and it was pretty small, but I assume that is normal for an urban Boston hotel. My only complaint is that the lobby coffee was only available at certain times (until 8:00 AM on Sunday morning), and the maid didn't refill the coffee pods in our room. The only option to get coffee was to pay for it in the attached bar/restaurant, which seemed like an unnecessary add-on charge.Show More

bornin63

Couples · November 2025

10/10

This hotel was funky and fun. The staff members with whom we interacted were terrific. The location was far closer to everything we wanted to do in Boston than we thought it would be. It was a reasona...This hotel was funky and fun. The staff members with whom we interacted were terrific. The location was far closer to everything we wanted to do in Boston than we thought it would be. It was a reasonable distance from Back Bay Station, and we walked to the Theater District for dinner and a show (it was a comfortable distance to walk). We'd never stayed in the South End before and would definitely stay there again. The room was small but offered everything we needed. It was surprisingly quiet. The bedding was amazing. We're not pet people (and this hotel is over-the-top pet friendly), but we found the room to be as clean, well maintained & comfortable as any in a pet-free hotel. We received two drink coupons on arrival and used them in the all-inclusive Trophy Room on the last night. We're in our early sixties, and the crowd was a lot younger, but we didn't feel out of place. This hotel was quite nice and a very relaxing place to stay. We'll stay again.Show More

amykS5476TO

Family · October 2025

6/10

The water was turned off from 8am to 1pm on October 30. 2025. The hotel should have alerted all affected clients ahead of time so that they could make appropriate arrangements. I left a day early and ...The water was turned off from 8am to 1pm on October 30. 2025. The hotel should have alerted all affected clients ahead of time so that they could make appropriate arrangements. I left a day early and the GM did refund all daily amenity fees and did not charge me a penalty for leaving early. That is what should have happened. I just don't think I should have had to ask for it. We were left feeling like we needed to accept the situation. The front desk was like "oh yeah...bummer". 8am?? I understand that work needs to take place...but the hotel clients should be given advanced notice and offered refunds. we should not have to ask for them. Travelers...know your rights! The hotel is high priced for what they offer. Rooms are very clean but very small. no closets. Bathrooms are small but nice. No lobby to speak of. The location is noisy. Lots of street noise is easily heard in the rooms.Show More

Amenities

General

Non-smoking rooms

Air conditioning

Non-smoking throughout

Front Desk Services

Luggage storage

Concierge service

Cashless payment available

Front desk (limited hours)

Housekeeping on request

Accessibility

Lift / Elevator

Internet

Free wired internet

Internet access

Pet-Friendly

Pets allowed

Pet bowls

Pet basket

hygiene

Guest rooms disinfected between stays

Cleaning standards that are effective against Coronavirus

Hand sanitizer in guest room and key areas

Sanitized tableware & silverware

Restaurant & Bars

Restaurant

Cleaning Services

Guests can opt-out any cleaning services during stay

Business & Work

Invoice provided

Safety & Security

Staff adhere to local safety protocols

Fire extinguishers

First aid kit available

Smoke alarms

Face masks for guests available

Key card access

Additional Amenities

Bicycle-friendly property

FAQs

Check-in starts at 04:00 PM, while you're expected to check out by 12:00 PM.

Staypineapple, A Delightful Hotel, South End's cancellation policy depends on the room type and the dates it’s booked around. Make sure to select your preferred cancellation policy when selecting your rooms.

Yes, breakfast is included with some of the rooms. However, some rooms include breakfast with an extra charge. Make sure to select your preferred meal option when selecting your room. Subject to availability.

Yes. This hotel provides free wifi connectivity along with your rooms.

No, this hotel does not offer parking facilities.

Yes, pets are allowed at this hotel. Additional charges and restrictions may apply. Please check the pet policy while booking or contact the hotel for more details.

Yes, children can stay at this hotel. Family-friendly rooms and amenities may be available. Some extra charges may apply depending on room configuration and the age of the children.

Need more than 8 rooms?

Property description

Charming European-Style Boutique Hotel in Boston's South End
Modern Amenities: Each room at Staypineapple, South End boasts a flat-screen TV, iPod docking station, and a luxurious walk-in marble shower in the private bathroom.
Convenient Services: Guests can enjoy free WiFi, a work desk, and a direct line to the 24-hour front desk for any needs that may arise during their stay.
Prime Location: Situated in the historic South End, the hotel is just a short stroll away from renowned restaurants and attractions, including the vibrant Back Bay area and upscale shops on Newbury Street.
Ready to experience the perfect blend of comfort and sophistication? Book your stay at Staypineapple, South End now!

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Fine print

Please note, guest must be a minimum of 18 years of age to check in. Please note that, Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

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Staypineapple, A Delightful Hotel, South End

Good

1551 reviews

Aug 28th – 29th 2026

1 Room, 2 Travellers

1551 reviews

Cleanliness

8.14

Services

9.11

Comfort

7.6

Amenities

8.63

Value

9.09

Location

8.65

Food

8.14

1985smn

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chrin22

10/10

bornin63

10/10

amykS5476TO

6/10

Amenities

FAQs

Property description

Show more

Fine print

Show more

1551 reviews

Cleanliness

8.14

Services

9.11

Comfort

7.6

Amenities

8.63

Value

9.09

Location

8.65

Food

8.14

1985smn

10.css-xp6yv9{margin:0;font-size:14px;font-weight:400;line-height:140%;font-family:Futura;color:#453C37;font-size:10px;font-weight:350;color:#7C7068;margin-left:4px;}/10

chrin22

10/10

bornin63

10/10

amykS5476TO

6/10

Amenities

FAQs

Fine print

Show more

10/10

10/10