If you’re looking for a fun and affordable place to stay in Boston that’s walkable to almost everything, Staypineapple is a fantastic choice in the South End. The hotel embraces a quirky theme with serious hospitality that makes it a memorable home base for any trip to the city.
Boston is one of my favorite cities to visit, as there’s always something different and unique to explore. It has so many different neighborhoods, each with its own vibe, and I really enjoyed staying in the South End.
Staypineapple in Boston is located within what feels like a neighborhood, but it also is an easy walk from the T. It isn’t the closest hotel to the Freedom Trail, but it didn’t take me much time to get there, and I loved this funky hotel.
I stayed here as part of a press visit, but my opinions remain my own.
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Where Did the Name Staypineapple Come From?
When I first heard the name Staypineapple, I have to admit I was a little concerned that it might be that kind of hotel. It isn’t. At all.
They go with the pineapple theme because the founder’s father called her his Little Pineapple when she was a child, and the nickname stuck. Pineapples are a traditional symbol of welcome and hospitality, which is the second reason and fit for the name.
I gotta tell you, they really go with the theme. The yellow and pineapples are everywhere from the decor in the room to the staircase by the elevators.
Long story short, this is a different kind of pineapple hotel. You can stop worrying and googling.
Book Your Stay at an This Affordable Hotel!
Smart Design In A Cozy Space
The hotel itself is fairly small and charming. The rooms aren’t huge either, but they designed them smartly to maximize space. Besides, when I visit Boston, I am there to see the city rather than spend time in my room.
They did things like installing a fold-out desk that reminds me of a Murphy bed and placing drawers for storage under the bed itself. The bed was ridiculously comfortable, as were the pillows. It was the perfect place to crash after a long day of walking.
A Warm Welcome And Refreshing Perks
I absolutely love so many of the fun amenities you find at Staypineapple. For example, when you check in, you get a coaster that is good for a welcome drink at the bar.
You can choose from beer, house wine, or non-alcoholic beverages. I chose a cider to accompany my dinner, and it was delightful.
The freebies didn’t stop there. When I got to my room, there was a reusable water bottle waiting for me that they had filled with purified water.
The bottle is mine to keep, and next to the reception desk, they have a water filling station with still, sparkling, and hot options. If you choose hot, make sure you put it in a container that can handle it.
Sweet Treats And Yellow Bikes
Continuing on the theme of free items, Staypineapple also has bikes to borrow in the hotel’s signature yellow. It’s a great way to get around the city quickly, and when you borrow them, they have bike locks and a helmet available to keep yourself and the bike safe.
When you get back to the lobby after a day exploring, you might find a treat waiting. They had the most adorable pineapple cookies in the afternoon, along with hot coffee and tea for guests.
Dining With The Locals At The Trophy Room
I enjoyed dinner at the restaurant attached to the hotel called The Trophy Room. With the server’s suggestion, I ordered a pizza and a bowl of New England clam chowder.
It was so good that I ate more than I had intended to and more than I probably should have. The chowder may have been some of the best I’ve found anywhere in Boston, including the one I tried on my Boston food tour the next day.
What I found most interesting is that the majority of the people eating and drinking at The Trophy Room were locals and not hotel guests. There were hotel guests too, of course, but you rarely find a hotel restaurant where locals choose to hang out.
Exploring The South End And Beyond
The location was easy to access from the T that I took from the airport, though obviously you can get a taxi or Uber. I also did a lot of walking and biking from the hotel itself to other locations in the city.
The hotel is in the South End, so the first day, I went everywhere from the Boston Public Library and Trinity Church. The next day, I headed up to the aquarium and through the Boston Common and even to View Boston at the Prudential Center.
Side note: I definitely suggest you head up to View Boston for the views, sunset and dinner. This is a relatively new attraction in Boston that not many people know about yet.
I found the neighborhood to be easy to access whatever part of Boston I wanted to explore. I’m from Chicago, so I walk everywhere, and I know many people might have taken the T instead, but I enjoyed walking and felt safe the entire time.
A Pet-Friendly Atmosphere
While my pets stay home when I travel, Staypineapple is incredibly dog-friendly. There is a nightly fee for this, but you can also get pup packages with treats and water bowls and more.
They do maintain an inventory of rooms with no dogs allowed for those who are allergic to them. The hotel does recognize that not everyone is a dog person.
Even if you don’t travel with your own pup, they have an adorable stuffed husky mascot named Dash. You can “adopt” him and bring him home for $25, and a portion of the fee goes to support local rescue organizations.
Enjoy Staypineapple, A Unique Boutique Hotel
Are you convinced yet? Book your stay!
I really enjoyed my stay, and I will absolutely look for them as I travel elsewhere. Staypineapple has locations in other cities from New York to San Diego, though I had not heard of them prior to my visit to Boston.
