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Staypineapple Boston Hotel

Website: staypineapple.com

Phone: (857) 444-6111

Cross Streets: Near the intersection of Chandler St and Berkeley St

26 Chandler St Boston, MA 02116 ·535.54 mi

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4.5
9 reviews
5 star
6 4 star
1 3 star
2 2 star
0 1 star
0
Tripadvisor traveler Ethan S 08/13/26

We had such a great stay at Staypineapple! The hotel was super clean, comfortable, and had such a fun, welcoming atmosphere. One of our favorite little touches was walking into the room and seeing the adorable stuffed dog sitting on the bed—it was such a cute surprise and immediately made us smile. The room was cozy, the bed was extremely comfortable, and the little details throughout the hotel really made it stand out from a typical hotel stay. The staff was also friendly and helpful. We would definitely stay here again and highly recommend it to anyone visiting the area!

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Tripadvisor traveler Ricardofreiresilva 07/14/26

Great staff, very friendly and helpful, great atmosphere! The location is also nice and easy. Rooms are more on the smaller side, but they are very comfortable, bed and pillows are superb. I will definitely use Staypineapple again from now on, when visiting US!

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Tripadvisor traveler Catie E 12/14/25

The room was very small!! Zero closet space and the bathroom was so tiny and there was no counter space. We wouldn't stay here again.

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Tripadvisor traveler galotgo 10/05/25

My bestie and I wanted to love StayPineapple Boston, and there were certainly aspects worth celebrating. However, significant issues with our specific room made what should have been a relaxing work-and-play trip exhausting and stressful.The PositivesThe hotel has a lot going for it. The location is absolutely perfect—centrally positioned with easy access to both popular tourist spots and authentic local neighborhoods. The cheerful yellow, green, and white color scheme and thoughtful interior design elements create a welcoming, joyful atmosphere that immediately lifts your spirits.The staff truly shines here. Everyone was friendly and helpful, with a special shoutout to Mitchell, who went above and beyond. I also appreciated the hotel's community partnership with a local dog rescue organization and their dog-friendly policy. The beverage selection was impressive too, including PATH water and protein drinks—thoughtful touches for health-conscious travelers.The DealbreakersUnfortunately, our room had serious problems that overshadowed these positives. The cleanliness wasn't up to standard, but worse was the shower situation. It leaked constantly, flooding the already tiny bathroom and rendering it essentially unusable throughout our stay.The real issue was the location of our room at the end of the hallway. The main door to our floor slammed repeatedly—day and night—disrupting sleep constantly. On our final night, a distressing incident involving another guest's loud, frightening screaming jolted us awake. Between the door slamming and this incident, we barely slept during our three-night stay. We left Boston as zombies rather than refreshed.The ResolutionThe hotel did credit us the amenity fee for our three nights, which I appreciated as a gesture. However, given the cost of the stay and the toll the sleep deprivation took on our entire Boston experience, it felt insufficient.Would I Return?Possibly, but only if guaranteed a room far from the main hallway door. The hotel's concept and many features are genuinely wonderful—it just requires careful room selection to avoid the noise issues we experienced. If you book here, specifically request a room away from floor entrance doors.

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Tripadvisor traveler Rachael W 10/04/24

A lovely couple of days spent in this hotel. Great location, clean and well-appointed. Would recommend. The bar downstairs was lively and welcoming. Well positioned for all attractions in Boston plus some good diners locally ideal for breakfast

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