Otis Cabin

With the coziest nook in all of the Berkshires, this peaceful, super kid friendly cabin is not to be missed. The enviable interiors will make you want to stay in by the wood stove all day, but there are so many good hikes and day trips in the area you may have to venture out at some point. Plus Great Barrington is only a short drive away - lots of great restaurants, bars and shops to explore!

Historic Berkshires Farmhouse

Built in 1820, this beautifully renovated farmhouse is a perfect mix of historic New England and minimal modern design. This spacious 3 bedroom, 2 bath home is an ideal spot for a family getaway (there's even a bedroom for kids). The covered porch looks out onto park-like grounds complete with a private brook. Can't you just envision drinking your morning coffee on the porch while the kids play in the yard? Book your weekend now! 

Overbrook House

This cabin is the ultimate Berkshires retreat. After you park, a winding path leads you through the woods and over a wooden bridge to the door of the rustic, secluded cabin. A babbling brook and majestic hardwood forest will be your only neighbors! A large stone fireplace, beautiful chef's kitchen, and clawfoot tub are waiting for you inside. With 2 bedrooms and the dreamiest loft, this cabin is perfect for a romantic getaway or a weekend with close friends. Put on some records and cozy up by the fire or soak up the sounds of nature out on the porch. Overbrook truly has it all!

Harold Parker State Forest

We've stayed at a lot of campgrounds and this is the one we always come back to over and over again. It's located only 20 miles outside Boston but is surrounded by 3,000 acres of state forest - so even though you're not that far away from the city you feel like you're in the middle of nowhere. The sites are spacious and private with top notch bathroom facilities close by. Plus there are miles of trails in the forest, ponds to swim in, and a quaint New England general store only a mile away. This spot will become your new go-to, we promise! 

1930's era Cabins on Cape Cod

If you're wanting a classic Cape Cod cottage experience - look no further. These 9 rustic cottages built in the 1930's will instantly ease your mind and transport you back to a time where life on the Cape was quiet, simple, and sans bumper to bumper traffic. Located on the outer Cape, the cabins are minutes from some of the best beaches in the state (both ocean & bayside) and super close to the Cape Cod rail trail. Plus these cabins are very pet friendly! Always a big plus.

Photo via Airbnb

Photo via Airbnb

The Pondhouse

A unique open air retreat that provides the best of both worlds - a super cozy cabin interior with no walls, only screens. Cuddle up in a warm bed with a book while listening to the crickets and gazing at the stars. Cook up a meal on the fire pit or just eat some pizza from the nearby town and roast s'mores for dessert. There's no electricity or running water, but a bathroom and shower are available close by.