Finest Airbnbs Close to Boston: The place to to Book This Winter

Berkshire Mountain retreat

Berkshire Mountain retreat | Photo courtesy Airbnb

Berkshire Mountain retreat | Photo courtesy Airbnb

If you want to book a stay nearby, you’ve come to the right place. New England is filled with some of the coolest, most adventurous, and gloriously quaint homes that you can call your own for a short while. Whether you are hoping to get away for a few days or even a week, we have it for you. Check out our list of the best Airbnbs near Boston when you feel like a need to escape. Find out in advance about the COVID-19 log of all households and, as always, don’t leave your mask behind.

Marblehead, Massachusetts
4 guests, $ 175 per night
Distance from Boston: 35 minutes
While dubbed the “tiny house” this Marblehead home, it offers plenty of space to relax and catch up on some much-needed relaxation. Steps from Salem Harbor and just 1 mile from downtown Salem, the choice is yours when it comes to grabbing a coffee, a quick bite, or even a stroll around town.
What guests say: “The house itself was beautifully decorated and very clean. It fit three of us very comfortably, with room for a fourth. The house is in a prime location and only a few minutes drive from downtown Salem. We enjoyed exploring Salem during the day and returning to a comfortable and quiet home at night. We would recommend this tiny house to anyone planning to visit the area! “Photo courtesy AirbnbYarmouth Port, Massachusetts
7 guests, $ 319 per night
Distance from Boston: One hour
Nothing says a weekend getaway to New England like spending time on Cape Cod. For breathtaking views of the water, you can enjoy a front row seat from either the private deck or this cottage in Yarmouth Port. The decor is pretty perfect too, so you may end up spending more time indoors than originally planned.
What guests say: “Really a great experience! Not only was the house beautiful with a fantastic location and view, the house had almost everything you could ever need, right down to the skunk spray (luckily we didn’t need that). “Photo courtesy AirbnbSanbornton, New Hampshire
4 guests, $ 257 per night
Distance from Boston: An hour, 30 minutes
Tucked away in the woods and 12 feet in the air, this New Hampshire treehouse has all your needs for a one-of-a-kind stay. With a stunning setup and an outdoor fire pit for frosty but not frozen nights, you’re back when the weather is warm or maybe next month – we wouldn’t blame you.
What guests say: “My friends and I loved staying in the tree house! The description was very accurate and we could see how much work and effort went into making this a spectacular Airbnb. Abby was very attentive and a great host. Highly recommend staying here! “Photo courtesy AirbnbNewbury, New Hampshire
4 guests, $ 456 per night
Distance from Boston: An hour, 30 minutes
This two story tree house in Newbury is conveniently located near Lake Sunapee and only a 5 minute drive to the ski slopes of Mount Sunapee. It’s important that we also mention the medieval-inspired interior, which is not only pristine but also perfect for snowy nights.
What guests say: “We had the perfect treehouse vacation – I can’t recommend it enough! The space, the property and the area were just breathtaking. We were in awe of the tree house and its history. “Photo courtesy AirbnbConway, New Hampshire
5 guests, $ 242 per night
Distance from Boston: Two hours
Located in Echo Lake State Park, you don’t have to travel far – if at all – to experience adventure on your weekend getaway to the White Mountains. The interior of the cabin, a beautifully decorated space with clean decor, is equipped with the necessary amenities and a fireplace so you can curl up on the couch. An added bonus? The place is dog friendly too, so you don’t have to leave your furry companion at home.
What guests say: “Nice place. Stylish decor. The morning coffee in front of the huge windows was perfect.”

Photo courtesy AirbnbLee, 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 quirky Berkshires getaway offers incredible views of the surrounding nature, including the property’s lily pond, which can be seen from the tower’s giant windows. The upstairs four-poster bed is another magical feature that will make you feel like you are far away.
What guests say: “If you want a fairytale experience in a rustic yet comfortable environment, you’ve found your dream stay in the Santarella Tower! It is so unique and absolutely perfectly located for amazing hiking trails, restaurants, city hopping, walks, star gazing and so much more. “Photo courtesy AirbnbLee, Massachusetts
8 guests, $ 281 per night
Distance from Boston: Two hours
If you’re looking for design inspiration, you’ve come to the right place. One step into this luxurious and energy-efficient home and you are already making notes for your next renovation. With an indoor fireplace, outdoor fire pit, mid-century tub, and dining area overlooking the forest, you’ll be glad to be left to your own devices.
What guests say: “Exceeded all possible expectations and we will be looking out for cancellations as we can’t wait to rebook. Really great hosts and space. Honestly, the best experience we had on Airbnb. “Photo courtesy AirbnbOtis, Massachusetts
4 guests, $ 167 per night
Distance from Boston: Two hours
This rustic cabin is another charming getaway in the Berkshires. It has an open floor plan, brand new kitchen and flooring, and a blackboard wall in case you have kids (or adults) who need entertainment. For a look at the place, visit the Otis Cabin on Instagram.
What guests say: “Impressive! What a phenomenal, easy stay. The space was beautiful and breathtaking with really thoughtful, design-oriented details. Such a comfortable, cozy place – and so peaceful.”Photo courtesy AirbnbBowdoinham, Maine
6 guests, $ 162 per night
Distance from Boston: Two hours
This two bedroom cabin in the small town of Bowdoinham has unique views of the surrounding forest and water. With windows overlooking the bay, you’ll be constantly reminded why you booked this place over your other options.
What guests say: “We had a great stay on the property! Such beautiful views filled with natural light. Although we visited when it was a bit cold we loved sitting outside by the fire pit as we watched the sunset on the water. “Photo courtesy AirbnbJamaica, Vermont
5 guests, $ 139 per night
Distance from Boston: Three hours
Another little home on our list, Apple Blossom Cottage in Vermont, has a personality all of its own. With chartreuse and pink on the outside and ties on the inside, this lovely little home is perfect for those looking for memorable stays. The home is also a short drive from Stratton Mountain, a favorite with New England and traveling skiers. If you’d like a different look at the place, you can watch a short video tour before booking.
What guests say: “An absolute gem of a rental. I could only stay one night but it was the BEST night I’ve slept in a while. The house is immaculate and has everything you could need. “

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Jillian Hammell is a thrillist writer. Follow her on Twitter and Instagram.

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