10 Charming Cabins in the Berkshires

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Are you planning an epic getaway to Massachusetts? Then you absolutely must stay in one of the best cabins in the Berkshires! The Berkshires is easily one of the most beautiful areas of Massachusetts. Situated in the western party of the state, it’s filled with outdoor adventures just waiting to be had.

This post includes all of the top Berkshires cabins in no particular order. No matter your budget, the number of people you’re traveling with, or the time of year that you have your adventure, you’ll be able to find a fantastic Berkshires cabin or cozy cottage to book on this list!

Cabins in the Berkshires

Woodland Cottage

brown cottage under a blue sky
Image courtesy of VRBO

First up is this beautiful Woodland Cottage that was completely renovated in 2020. It’s family-friendly and is located in Otis, Massachusetts, and can sleep up to eight people per night. So, it’s perfect for a huge get-together in the area!

The house has three bedrooms, two bathrooms, a living room, deck, kitchen, and more. There’s also tons of outdoor space and even outdoor furniture on the deck so you can enjoy nature while sipping your morning cup of coffee.

The location of the Woodland Cottage is fantastic. With just a short drive, you can get to Jiminy Peak, Butternut, and even Tanglewood. There are quite a few towns nearby, including Great Barrington, Lenox, and even Lee. Lee, in particular, has terrific outlets if you want to do some shopping during your trip!

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Ski Mountain Cabin

interior of a cabin living room with a white couch
Image courtesy of VRBO

Next, is the Ski Mountain Cabin, aptly named because it’s situated near four different ski areas! It’s located in Sandisfield and has three acres of land, so it’s perfect if you want to do some outdoor exploring. The home can sleep up to ten people at a time, and it’s just shy of 2000 square feet, so it’s definitely one of the larger cabins on this list of best cabins in the Berkshires.

The cabin features four bedrooms, three bathrooms, a kitchen, outdoor space, a huge living room, and of course, a deck. The living room is definitely the main showstopper of the cabin, featuring a furnace and tons of huge windows allowing for lots of natural lighting.

A short drive from the cabin will bring visitors to Otis Ridge, Jiminy Peak, Catamount, or Butternut ski areas. It’s situated in a similar spot as the cabin above (Woodland Cottage), so Stockbridge, Great Barrington, Lenox, and Lee are other nearby places to explore.

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Quaint A-Frame

Green and red a-frame cabin in the woods
Image courtesy of VRBO

One of the more unique cabins in the Berkshires that you won’t want to miss out on is this Quaint A-Frame! It’s in Becket in Sherwood Forest. It’s a bit smaller and can host up to five guests at a time. From the outside, the A-frame looks so magical! Just imagine if you were to visit the Berkshires in the snow.

Inside the cabin, there’s a bedroom, bathroom, living room, kitchen, and a loft. There are also no neighbors really in the area, making the home feel like a true natural getaway. If you’re tall, though, definitely be careful making your way around the home because of its shape! You might easily bonk your head, but it’s worth it for the beauty of the home.

Unlike other places on this list, this cabin is definitely one you’ll want to book if you’re genuinely looking to get away. Have a peaceful fire, watch the stars, and just embrace the paradise and tranquility of the location.

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Lakefront Cottage

brown cabin right along the lake with a dock
Image courtesy of VRBO

This Lakefront Cottage in Becket is one that’s perfect for a family getaway! It’s right on the lake (like the name suggests), and there’s even a dock, so you have easy access to the water. The home is a bit on the smaller side and can accommodate up to four guests at a time within 700 square feet.

The home has a kitchen, living room, two bedrooms, and a bathroom. The home is quite charming. Note that the area that the home is in does have a quiet policy that starts at around 10 p.m.; if you know you’re traveling with a louder bunch, you may want to book a different place on this list.

The outside of the home is the true part that you won’t want to miss. There are two decks, a dock, and outdoor furniture so that you can enjoy your food with a view. Plus, the cottage has three different kayaks and a canoe, so you can go out on the water without having to bring your own boats.

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Log Cabin in the Woods

aerial view of a log cabin
Image courtesy of VRBO

Located in Charlemont, this Log Cabin in the woods is absolutely beautiful! It’s nestled right in the woods and has impeccable views of the nearby mountains. The home can sleep up to twelve guests at a time throughout 2400 square feet, so the house itself is genuinely quite large.

There are four bedrooms, two bathrooms, a kitchen, deck, living room, and tons of outdoor space. There’s even a fire pit with outdoor furniture so you can get warm by the fire at night, as well as a jacuzzi located on the deck. Even though the home can host a large number of people, it’s a fantastic place to stay if you’re looking for a romantic getaway!

Whether you visit in winter or summer, you’ll have a fantastic view through the windows that allow natural lighting throughout the cabin. Be sure to wake up early to catch the beautiful sunrise over the mountains; you won’t want to miss it. Maybe even pop into the jacuzzi and take in the view!

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Williamstown Hiking Cabin

dog standing in front of a cabin
Image courtesy of VRBO

If hiking is your thing, then you’ll want to book a stay at this Williamstown cabin. Williamstown is a beautiful small town to stay at, and it’s not that far of a drive from southern Vermont or even New York, making it perfect if you want to explore more of the surrounding states!

The home was built in the 1900s and can host up to five guests at a time. The interior is very quaint and has two bedrooms, two bathrooms, a living room, kitchen, deck, and more. It’s been owned by the same family for around fifty years, so every room truly has its own story!

This cabin is perfect for hiking because you can actually walk the area behind the cabin and get lost in the Mount Greylock area, which is absolutely filled with tons of different hiking trails. Be sure to also pop into Williamstown and enjoy the beauty of the small town.

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Otis Reservoir Cabin

interior of a log home with a fireplace
Image courtesy of VRBO

Another great one of the cabins in the Berkshires that’s located in Otis is this one! The interior is exactly what you’d want out of a cabin. There’s a fireplace, tons of seating for family time, lots of natural lighting due to the windows, and hardwood everywhere you look. Plus, the cabin is just a very short walk to the lake!

This cabin can house four different guests at a time. There are two bedrooms, a bathroom, a living room, and a kitchen. It’s perfect for a family of four going on a family vacation in the area, mainly because the cabin is so charming.

Another fantastic feature of this cabin is the screened porch, so you can sit outside without worrying about the bugs that often come to New England in the summer. Visitors can go to Jiminy Peak, the Hancock Shaker Village, or even Six Flags New England with a short drive.

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Stockbridge Cabin for Four

living room inside a home with white walls
Image courtesy of VRBO

The Stockbridge cabin is another one that’s located near the lake! It’s definitely more of an airy cabin, but it’s absolutely breathtaking. The space feels large inside due to the white walls and ample windows, which really helps to open the house up.

Despite being 700 square feet, the cabin can host six guests at a time. There are two bedrooms, two bathrooms, a kitchen, deck, and lots of outdoor space. The deck also has outdoor seating, so you can sit outside and enjoy the view and beautiful weather while still staying covered.

Nearby activities for the cabin include the Norman Rockwell Museum, Stockbridge Town Beach, and even Tanglewood. Be sure to stop and explore lots of the outdoor spaces as well because there are tons of fantastic hiking trails in the surrounding area. 

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Oak Hill House

A cozy scene with a fire roaring in the fireplace at a Berkshires MA cabin
Photo courtesy of Oak Hill House; doesn’t this Berkshires cottage look so incredibly cozy??


This gorgeous 3 bedroom, 3 bath cottage in the Berkshires is an updated dream of a place to stay in MA! Not only can it sleep up to 8 people, but each bedroom has its own dedicated bathroom, allowing everyone extra privacy during their stay at this Berkshires gem.

Located on 12 wooded acres, this Berkshires gem is convenient for all sorts of fun Berkshires things to do, so whether you decide to hunker down in this cozy cottage or just use it as a home base for your explorations, you’re in the perfect place for it either way!

With a wood burning fireplace, outdoor fire pit, and hot tub, you might just decide there’s no need to stray too far from this cute Berkshires cottage.

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Great Barrington Cottage

navy barn under a blue sky
Image courtesy of VRBO

Last but not least is a cottage located in the Great Barrington/North Egremont area! It’s a beautiful cabin with unique decor inside. The home can sleep four guests at a time and used to be a barn which is what makes it so different from other places on this list.

The home has one bedroom, a bathroom, a kitchen, and more. There’s also quite a bit of outdoor space, including a firepit that the owners created which has seating surrounding it. Just imagine the fun cookouts you can have there, especially in the summer!

This cabin is an excellent area with Catamount and Butternut ski areas just a short drive away. There’s also the Berkshires at your doorstep. Enjoy the outdoors, go on a hike, or even stop by one of the local restaurants to mingle with those who live in the area and enjoy some local music!

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Hopefully, this post of the best cabins in the Berkshires has helped you find the perfect place to stay during your trip. From larger cabins to smaller ones and perfect for a romantic getaway, this area truly has it all!

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