Located in Boston's vibrant South End, Staypineapple, A Delightful Hotel offers a prime urban experience for travelers seeking convenience and comfort. This smoke-free boutique hotel provides easy access to the city's most iconic attractions. Complimentary bicycles available for guest use 56 modern guestrooms with premium bedding Bar and lounge for relaxation and refreshments
Staypineapple, A Delightful Hotel, South End offers Complimentary coffee, Smoke-free property, Coffeemaker, Bathrobes, Hair dryer, Free bottled water, Free WiFi, Pets allowed, HDTV, Bicycle rentals, Bar/lounge, Coffee shop or cafe, Wedding services, Gift shop.
Staypineapple, A Delightful Hotel, South End is located at 26 Chandler St, Boston.
Staypineapple, A Delightful Hotel, South End has an average rating of 4.3 out of 5 based on 917 guest reviews. It holds a 3-star Stars rating.
1 King Bed
South End Corner King
1 King Bed
Back Bay King




+19

Located in Boston's vibrant South End, Staypineapple, A Delightful Hotel offers a prime urban experience for travelers seeking convenience and comfort. This smoke-free boutique hotel provides easy access to the city's most iconic attractions.
Staypineapple, A Delightful Hotel, South End offers a quirky and comfortable stay in the heart of Boston, known for its pineapple-themed decor and friendly service. Recent reviews highlight the location's convenience and the hotel's welcoming atmosphere, while some guests have raised concerns about room size and noise levels from the on-site bar.
Lovely hotel with many quaint features and amazing perks. Bed was so comfortable with cozy robes and the coffee machine was special highlight for drip coffee. You get a drink on the house, free bicycle access to explore the city. And the service was so prompt and attentive. Mitchell especially was very responsive to many complaint about cable tv and got it resolved very quickly
The room and bathroom are incredibly small. Bsically you have a bed and 2 night tables and not much else. There isn't a dresser or closet to put your clothes in. The bathroom doesn't have a vanity or anywhere to store your toiletries. Doing my makeup was incredibly difficult with nothing but a sink under me. The only place to put your clothes is on wall hooks or under-bed drawers. There isn't anywhere to sit other than the bed or the oddly stained ottoman, which I chose to stay away from - it gave me the ick. The only surface to put your items on is along the window. The staff was friendly and helpful, the "free" water bottle is a nice touch (this is probably covered by the resort fee they charge) and I did keep it. They also stored our luggage for the afternoon while we were tourists. The common hotel amenities are lacking, no blowdryer, no ironing board or iron, no little toiletries. They may have been available at the front desk but as I didn't need them, I didn't ask. The TV "satellite" kept cutting out and the selection of channels was sad. First hotel I've seen in a long time that didn't have any streaming options available. Overall, it's a cute hotel. Cool bar that was pretty full on a Friday night, nice safe area, but the lack of closet, dresser or bathroom counter make this hotel a bit overpriced. It was fine for one night, but if you're planning on staying more than that I would suggest somewhere else.
Im writing this 3 years late so maybe things have changed, but I remember this being one of my favorite hotels I've ever stayed in. The pineapple theme is sooo cute, and the bed was very comfortable. Room was very clean. I stayed here in January 2023. Upon arrival I was greeted by this cute dog plush on my bed. I love small touches like that. I didn't have a pet with me, but I noticed there were water bowls and dog treats available throughout the hotel which I thought was sooo cute Room was spacious and comfortable. I love the ceiling accents in this hotel, the architecture is gorgeous Had breakfast one day at Staypineapple and it was yum. Also, they had these complimentary sugar cookies that look like pineapples in the lobby and they were so good. There's also a bar. I didn't get to try it but it looked nice from what I saw My stay at this hotel felt decently luxurious for the price. I got my room at a deal, it was around $550 for 3 nights which I think is relatively affordable for Boston Location is right next to one of the major train stations and is like a 10 minute walk to downtown Staff was sweet and accommodating. Next time I am in Boston I would stay here again
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.
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 were very friendly and helpful with suggestions for local coffee shops. I highly recommend it.
Five stars for Staypineapple Boston! The location is unbeatable for exploring downtown. The hotel is exceptionally clean and has a really cool, modern aesthetic that stands out from other places I've stayed. Loved the quirky details and the friendly service. I’ll definitely be staying here again on my next trip to Boston.
So dog friendly: love that dogs can be in the lobby and they get water bowls and poop bag dispenser. Cute area. Nice restaurants to walk to. No parking on site. Use spot hero to find spots to pay for. Wish the restaurant had more hours of operation
A friend and I booked our stay for a birthday evening celebration out in Boston. The service was absolutely wonderful! We were allowed an early check-in with no fuss, & had every need met & anticipated. While the room was small, it was just our launchpad for our outing & a place to sleep, so it was great for our needs. The location of the hotel can’t be beat and the on-site bar was fun to hang out in. We’ll definitely book again for a super easy Boston stay.
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!
My husband and I stayed one night in a corner room on the third floor. We absolutely love the eclectic atmosphere and decor. We especially love the bedding and the fact that we had comfy separate duvet covers. I asked gbchat and found out you can purchase the entire bedding set including the cute stuffed husky. Unfortunately the bedding is sold out but I will definitely get it at one point. We will absolutely return and stay again. Loved the coasters to use for a free drink. The metal water bottles to refill with sparkling or water in the lobby. So many perks. Our new favorite stay in Boston. Also when you submit a Google review they give you a cute little candle. All class this place.