Unique Airbnbs to rent in and around Boston

Sure, you’ve probably already taken a cruise around Boston Harbor, but how about sleeping on it for a night? Docked in a Charlestown marina is a boathouse-turned-studio perfect for a sea-happy couple (but no one else; quarters are snug). There’s no kitchen, but there is a pool on the marina, and there’s even a tiny deck with Adirondacks so you can wave at fellow sea dogs. Pro tip: skip the rental car (parking’s expensive and difficult) and take a water taxi from Logan straight to your boat.

Get away from it all… 30 feet in the air! This treetop oasis is accessed via a suspended path. You’ll have to bring a sleeping bag, but otherwise this little forest sanctuary has it all, from a fridge and a wood burning stove to electricity and Wi-Fi.

This dreamy apartment feels like something straight out of a sitcom about aspiring twentysomethings in the big city, maybe. Grab an adventurous bestie for a weekend of sightseeing and shopping—the apartment is literally atop Charles Street in Beacon Hill, the most picturesque street in the city. No fighting over bedrooms, as both are impeccably appointed.

This fairytale guesthouse on the Santarella Estate in the Berkshires is both charming and romantic, with plenty of quiet seclusion. A former sculpting studio, the two-story cottage is surrounded by a lilly pond, babbling brook, and gardens.

Stay in one of New England’s quintessential symbols: a lighthouse. This unique property is completely renovated while retaining its historic elements and charm. Climb the spiral staircase to view the Atlantic from the lantern room and sleep in the former keepers home. The kitchen is fully equipped, and there’s a private beach on site. Several other Cape Cod beaches and towns are within a short drive.

A dark wood library with leather couches astride a massive fireplace? A pool table and wet bar? A ballroom? A private roof deck? An elevator? This 1860s single-family brick row house in the South End just drips with history—and, in fact, it once served as a gathering place for civil rights leader A. Philip Randolph. Once you’ve managed to extricate yourself from these elegant 19th century trappings, you’ll find yourself in the middle of a trendy area filled with hip bakeries, restaurants and boutiques.

Time to gather the extended fam and pretend to be Harvard intellectuals for a weekend. This stunning, five-bedroom Mansard Victorian is just a 10-minute walk to Harvard Yard. It’s a classic Cambridge abode—lovely yet unpretentious, combining an airy, modern kitchen with quirky decor, comfy furniture and the perfect yard for frolicking young’uns while the adults enjoy a glass of wine on the adjoining deck.

It’s the second oldest home in Beacon Hill, itself the oldest neighborhood of Boston. But what makes this space so irresistible is that it feels like a secret abode: A tiny jewel of a basement studio with brick walls peeking out between twee antique furniture. This is true city living (just be aware of the late night noise), which means you can walk or take public transportation almost anywhere.

As centrally located as this Bay Village brownstone is, it’s going to be hard to get yourself out the door—the decor is just that arresting. A predominantly white canvas serves as background to pristine mid-century lamps and furniture, as well as wall art both minimalist and splashy. The modernist, angular kitchen feels like it belongs in a museum, and the intimate side patio is the perfect spot for a morning coffee while you plot the day’s activities.