Staypineapple, A Delightful Hotel, South End Boston

Boston, MA · Hotel

Rating
4.4/5
★★★★☆ 4.4
Reviews
20
Rank in Boston
#43
of 148 hotels
City Percentile
67%
rating percentile
Address
Staypineapple, A Delightful Hotel, South End Boston, 26 Chandler St, Boston, MA 02116
Phone
(866) 866-7977
Website
www.staypineapple.com/south-end-boston/?utm_source=google&utm_medium=organic&utm_campaign=GMB&utm_term=spb

Staypineapple, A Delightful Hotel, South End Boston is a hotel located in Boston, MA. It is one of 148 hotels listed in Boston. Its 4.4-star rating is above the Boston city average of 4.2 stars. There are 10 photos associated with this location.

Customer Reviews

★★★★★ 5.0 Liz Katz · Mar 2026

I really enjoyed my experience here...any hotel where there is a bucket of dog biscuits in the lobby is good by me. The best way I can describe it is that it is quirky with its own vibe. When I entered the room, I was greeted by a plush dog (which I took home for $25 - all proceeds go to local animal shelters) and a giant pillow that said "sleep with me" (which I did). It had quaint yellow and pineapple accents everywhere including on the ceiling; a pineapple stand which had USB ports in it; and the spare toilet paper roll which was wrapped in yellow and had green tissue paper coming out of the top. After a long day of travel, it put me in a really good mood. The room was clean and although small, had ample places to store my clothes in drawers under the bed. The folks at the front desk

Trip.com Member · Aug 2025

Conveniently located hotel located a few blocks from the commuter rail backbay station. Hotel staff were great and allowed us to check in early upon arrival and store our luggage at check out so we could further explore the city. The rooms are small, bedding is best for someone under 5’9, otherwise it was a great home base for a weekend trip to the city.

Clairesc06 · Jan 2026

Delightful hotel in a nice location. Staff were great, special shout out to Mitchell & Rashawn who were very helpful & always gave us a warm welcome on our return from a full-on day of sightseeing. The rooms are not huge but clean & well laid out, perfect for what we needed. The hotel is walking distance of the station to get to other parts of the city or further afield, we used it to get to Salem which was relatively easy. Breakfast is only available on site at the weekends so bear this is mind if you are staying during the week. All in all a great stay & would recommend to others.

★★★★★ 5.0 Inna Hurley · Jan 2026

My husband and I had a great stay at Staypineapple Boston! The receptionist was very friendly and welcoming from the moment we arrived. The room was cute and quirky, with bright yellow accents, super soft sheets, and all the necessary toiletries — which smelled amazing with tropical scents. Such a fun, comfortable vibe. The bar downstairs is a perfect spot to finish your day with a drink or a quick bite to eat. The location is excellent — close to all the action, but still quiet enough to relax. The cleaning team did a wonderful job keeping everything spotless and were helpful in answering our questions. We’ll definitely be back soon. Highly recommend this hotel for its location, amenities, and price!

★★★★★ 5.0 Patricia Sullivan · Mar 2026

What a wonderful weekend at Stay Pineapple. The staff like Mitch were extremely friendly and helpful. The room was very clean, comfortable and was decorated for my birthday which was a delightful surprise! Loved the location- we walked everywhere! We will be back.

Services

Hotel

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This listing is informational. Contact the business directly to verify credentials, services, and availability.