Cool Airbnbs Near Boston To Book This Winter

Brb packing a bag

Berkshire Mountain retreat
Berkshire Mountain retreat | Photo Courtesy of Airbnb
Berkshire Mountain retreat | Photo Courtesy of Airbnb

If you’re looking to book a nearby stay, look no further. New England is filled with some of the coolest, most adventurous, and gloriously picturesque homes that you call your own for a short while. Whether you’re hoping to get away for a few days—or maybe even a week—we’ve got you covered. Check out our list of the best Airbnbs near Boston for when you’re feeling like you need to escape. Be sure to read up on all of the homes’ COVID-19 protocol prior, and as always, don’t leave your mask behind.

A Tidy Tiny House Near Salem

Marblehead, Massachusetts
4 guests, $175 per night
Distance from Boston: 35 minutes
Despite being labeled a “tiny house,” this home-away-from-home in Marblehead has plenty of space for lounging and catching up on some much needed relaxation. Just steps away from Salem Harbor and only a mile away from downtown Salem, you’ll have your options if you decide to venture out for coffee, a quick bite, or even a stroll around town.
What guests say: “The house itself was beautifully decorated and extremely clean. It fit three of us very comfortably, with room for a fourth. The house is in a prime location and only a few minute drive to downtown Salem. We enjoyed exploring Salem during the day and coming back to a comfortable and quiet home at night. We’d recommend this tiny house to anyone looking to visit the area!”

Photo Courtesy of Airbnb

Comfy Cottage on the Cape

Yarmouth Port, Massachusetts
7 guests, $319 per night
Distance from Boston: One hour
Nothing says a New England weekend getaway like time spent on Cape Cod. If you’re looking for breathtaking views of the water, you can enjoy a front row seat from either the private patio or nestled inside this Yarmouth Port cottage. The decor is pretty perfect too so you might be spending more time indoors than you originally planned.
What guests say: “Truly an amazing experience! Not only was the house beautiful with an amazing location and view, the house had almost anything you could ever need, right down to the skunk spray (luckily we didn’t need that).”

Photo Courtesy of Airbnb

A Treehouse Built for Wintry Stays

Sanbornton, New Hampshire
4 guests, $257 per night
Distance from Boston: One hour, 30 minutes
Tucked away in the woods, and standing 12 feet into the air, this New Hampshire treehouse hits all your needs for a unique stay. With a stunning setup, and outdoor fire pit for frosty but not frostbitten nights, you’ll be back when the weather’s warm or maybe next month—we wouldn’t blame you.
What guests say: “My friends and I loved staying at the treehouse! The description was very accurate and we could tell how much work and effort went into making this a spectacular Airbnb. Abby was very responsive and a great host. I highly recommend staying here!”

Photo Courtesy of Airbnb

Two-Story Treehouse Near the Slopes 

Newbury, New Hampshire
4 guests, $456 per night
Distance from Boston: One hour, 30 minutes
For those exclusively looking for aerial views, this two-story treehouse in Newbury is conveniently located near Lake Sunapee and only a 5 minute drive to the ski slopes at Mount Sunapee. It’s important that we mention the medieval-inspired interior as well, which is not only immaculate but perfectly crafted for snowed-in nights.
What guests say: “We had the perfect vacation at the treehouse - I cannot recommend highly enough! The space, the property and the area were just stunning. We were in awe of the treehouse and its story.”

Photo Courtesy of Airbnb

Chic Cabin in the Woods

Conway, New Hampshire
5 guests, $242 per night
Distance from Boston: Two hours
Located in Echo Lake State Park, you won’t have to travel far for adventure—if at all—during your weekend getaway to the White Mountains. The cabin’s interior, a gorgeously decorated space with crisp decor, is equipped with the necessary amenities and a fireplace for when you’re curled up on the couch. An added bonus? The place is also dog-friendly so you don’t have to leave your furry companion at home.
What guests say: “Great location. Stylish decor. Morning coffee in front of the huge windows was perfect.”

Photo Courtesy of Airbnb

Enchanted Tiny Tower

Lee, Massachusetts 
2 guests, $235 per night
Distance from Boston: Two hours
You’ve heard of a tiny house, but have you heard of a tiny tower? This whimsical stay nestled in the Berkshires offers incredible views of its surrounding nature, including the property’s lily pond which can be seen from the tower’s giant multi-paned windows. The canopied bed upstairs is yet another magical feature that will have you feeling like you’re far, far away. 
What guests say: “If you want a fairytale experience in a rustic yet comfortable setting, you have found your dream stay at the Santarella Tower! It’s so unique and absolutely perfectly situated for access to amazing hiking, restaurants, town hopping, walks, stargazing, and more.”

Photo Courtesy of Airbnb

A Modern Minimalist’s Dream Home

Lee, Massachusetts
8 guests, $281 per night
Distance from Boston: Two hours
If you’re looking for design inspiration, look no further. One step into this luxurious and energy efficient home, and you’ll already be taking notes for your next renovation-spree. With an indoor fireplace, outdoor fire pit, mid century tub, and dining area looking out into the woods, you’ll be happy to be left to your own devices.
What guests say: “Exceeded every possible expectation and we will be on the lookout for any cancellations as we can’t wait to rebook. Truly amazing hosts and space. Frankly, the best experience we have had on Airbnb.”

Photo Courtesy of Airbnb

Scandinavian-Inspired Spot in the Berkshires 

Otis, Massachusetts 
4 guests, $167 per night
Distance from Boston: Two hours
Another charming stay in the Berkshires, this rustic cabin features an open floor plan, brand new kitchen and floors, and a chalkboard wall in case you have any kids (or adults) that need entertaining. To take a peek at the place, check out the Otis Cabin on Instagram.
What guests say: “Wow! What a phenomenal, easy stay. The space was beautiful and breathtaking with really thoughtful, design-minded touches. Such a comfy, cozy place - and so peaceful.”

Photo Courtesy of Airbnb

Unbeatable Views at this Bayfront Escape 

Bowdoinham, Maine
6 guests, $162 per night
Distance from Boston: Two hours
For something serene, this two-bedroom cabin found in the small town of Bowdoinham offers one-of-a-kind sights to the surrounding forest and water. With windows looking out at the bay, you’ll have a constant reminder why you chose to book this place over your other options.
What guests say: “We had a great stay at the property! Such beautiful views, filled with natural light. Though we visited when it was a bit chilly, we loved sitting outside with the firepit as we watched the sun setting on the water.”

Photo Courtesy of Airbnb

The Groovy Apple Blossom Cottage 

Jamaica, Vermont
5 guests, $139 per night
Distance from Boston: Three hours
Yet another tiny house on our list, the Apple Blossom Cottage in Vermont has quite the personality. With pops of chartreuse and pink on the outside and tie dye on the inside, this lovely little home is perfect for those looking for memorable stays. The house is also a short drive away from Stratton Mountain, a favorite amongst New England and traveling skiers. In case you want to get another look of the place, you can check out a quick video tour before you book.
What guests say: “An absolute gem of a rental. I could only stay one night but it was the BEST night of sleep I’ve had in a while. The house is spotless and has every little thing you could possibly need.”

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Jillian Hammell is a contributor for Thrillist. Follow her on Twitter and Instagram.