When you think about fall in New England, you envision a blaze of red, yellow, and orange foliage streaking the landscape. During the autumn months, the one thing that might beat sitting on the porch of a New England inn with a cup of hot apple cider is sleeping among the trees.
There are nearly 270,000 treehouses around the world on Airbnb, but North America takes the cake for hosting the most treehouse stays. Their popularity has soared over the last few years with the number of treehouses on Airbnb climbing more than 65 percent from 2022 to 2024.
James “B’fer” Roth has 25 years of treehouse building under his belt. He’s one of the designers for The Treehouse Guys, a partnership with Chris “Ka-V” Haake based out of Warren, Vermont. “In the last five years or so, about 80 percent of our clients have been folks that want to build a treehouse to use as a rental,” says Roth. He believes the one big draw to treehouses is about a needed connection to nature. “When you’re up in a tree you’re somewhat disconnected. And I think that disconnectedness is even more important now that people are so dang addicted to looking at phones for information and not just being.”
What makes New England a prime spot for treehouses? According to Roth, the trees of New England are a sturdy foundation for these magical dwellings. “Hardwood trees, the deciduous trees like maples, oak, hickory, and beech, are great because of the density of the wood.” And, of course, you can’t deny the beauty of these trees as the leaves change color in the fall.
(9 unexpected places to see fall foliage in the U.S.)
1. Winvian, Litchfield, Connecticut
Situated on 113 acres, two-thirds of the Winvian estate borders the White Memorial Conservation Center, a wildlife sanctuary established in 1913 for the preservation of over 4,000 acres of woodlands, fields, and water. The property has 18 very different cottages, ranging from one with a Coast Guard helicopter sitting in the middle to a rustic log cabin.
Winvian’s two-story treehouse cottage sits 35 feet above the forest floor, surrounded by beech and maple trees, and is known to sway in the wind. The angles of the walls and the trees—close enough to see lichen—inspire the playfulness of a childhood treehouse all while providing a luxurious experience with the jetted tub and a gas fireplace on each level. You can use one of the provided bikes to head over to the main house, where chef Chris Eddy serves meals as elegant and beautiful as the fall foliage, or over to the spa building for a soothing massage.
(Here are the best places to travel during ‘shoulder season’)
2. Mink Cove, Wareham, Massachusetts
What started as a dream for a daughter who is now all grown up has become a dream come true for travelers. Tucked within an inlet off of the Atlantic Ocean sits Mink Cove treehouse. Sketched by Butch Ripley and his eight-year-old daughter and built from salvaged wood, the treehouse is small, as treehouses are meant to be, with a narrow winding staircase to its upper level. The house is adorned with twinkle lights and is an enchanted retreat among red and black oak trees. It has a private outdoor shower where only the squirrels will see you, a small bathroom, coffee nook, and fridge. Making this treehouse stay that much more magical is the smell of the nearby ocean.
3. Twin Farms, Barnard, Vermont
It’s hard to beat fall in Vermont. Just up the road from Silver Lake and one Vermont’s oldest general stores, The Barnard General Store, is the private, luxurious, and all-inclusive oasis known as Twin Farms. Landscape architect Dan Kiley worked to ensure that each experience felt integrated with its surroundings, and the Twin Farm treehouses follow the same philosophy. Designed with the hilly topography in mind, the treehouses allow guests to enter at ground level and, without ever climbing a step, arrive at a deck that sits about twenty feet high in the trees.
The treehouse boasts a bathroom with a soaking tub, large shower, and heated floors. Fall asleep in a cloud-like king-sized bed while looking out at the trees, and start up the modern gas fireplace to stay even more cozy. If you want even more treehouse in your life, you can hike to the Doug’s Treehouse Folly at Knobbs Hill, where a thoughtfully prepared picnic lunch will be waiting for you, or enjoy a farm-to-table and seasonally inspired meal at one of their two on-site restaurants.
4. Tiffany Hill Treehouse, Sunapee, New Hampshire
A five-minute drive from Mount Sunapee State Park, and surrounded by conifers, oak, birch, and beech trees that turn yellow and orange in the fall, you will find the charming Tiffany Hill Treehouse. This two-bedroom treehouse, supported by a sturdy oak tree, has radiant heat flooring, a propane fireplace, arched doorways, a functional kitchen, wraparound porch with a fun basket pulley system for groceries, and thoughtful design touches, like a saddle mirror and stirrup hand towel bar, that make you smile from room to room.
Drive 10 minutes to Newbury to grab a bite at Bubba’s Bar & Grille, digest with a walk on the dock, and then treat yourself to ice cream at Sanctuary Dairy Farm Ice Cream where the donkeys lean again the gates to have their long ears caressed.
5. Oaktagon Tree House, Monmouth, Maine
Kent Ackley, a registered Maine guide, saved a Monmouth island 25 years ago from a developer with dreams of killing its integrity and ecosystem. While 1 Big Sustainable Island isn’t one of Richard Branson’s islands and there are no spa treatments, it’s a truly special place to connect with nature with included access to canoes, fishing rods, a rope swing, your own private dock, and a hot shower powered by propane.
At the center of the Oaktagon yurt-style treehouse is an oak tree that serves as the center of the structure. Inside, there’s a loft with a queen-sized bed, two futons downstairs, a wood stove, a small kitchen, and even your own private composting toilet. You can watch the tree sway in the wind from your living room, and at night you might hear the sounds of acorns dropping from its branches onto the wraparound deck. Don’t forget to bring along some biodegradable shampoo and take a peaceful morning bath in the lake, a short walk from the treehouse down a trail, and right off of your own private dock.