20 Top Treehouse Rentals in Massachusetts

Explore the top 20 treehouse rentals in Massachusetts, from whimsical cottages to modern retreats, perfect for your next getaway. Ideal for travelers seeking unique stays.

Tobi Miles
July 5, 2024
Explore the top 20 treehouse rentals in Massachusetts, from whimsical cottages to modern retreats, perfect for your next getaway. Ideal for travelers seeking unique stays.

Massachusetts is filled with historic landmarks, lovely fall colors, beautiful nature, and is the perfect place to take your next trip. With treehouses located all around the state, you’re sure to find the ideal getaway for whatever you’re looking for.

Massachusetts has the perfect trip for you, no matter what you’re looking for. Stay in a modern treehouse filled with all the amenities you have at home. Relax in a humble cottage overlooking the water. Soak in hot tubs under the stars, roast marshmallows over fire pits, and live the life of luxury amidst the trees.

With so many treehouse options from whimsical cottages out of a fairy tale to modern multi-story abodes, doing research is a must. Luckily, this list should help point you in the right direction and get you to your perfect retreat into the woods.

1. Sandytoes Treehouse (Cape Cod)

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This multi-level treehouse is large, luxurious, and filled with everything you could want or need. With space to sleep up to eight, “Sandytoes” is the perfect retreat for a group of friends or family. It’s spacious, cozy interior and proximity to the water will have you wanting to stay forever.

This treehouse offers stunning views of Cape Cod from the top of its six story construction. The beach itself is also accessible via a short, paved walkway, so you don’t have to limit your enjoyment of the water to the view.

The treehouse is also located on 15 acres of isolated forest, so you’ll not only have access to water activities, but plenty of hiking as well. Outside, guests also have access to the elevated deck with outdoor furniture, a gas grill, and the Sandytoes garden.

The proximity to the waterfront also offers a perfect opportunity to go shell hunting. You may even find some blue mussels or sea clams for dinner in the inter-tidal zone.

The interior of the treehouse is also outfitted extensively. Throughout its six levels you’ll find a well-equipped kitchen, plenty of room to relax, a fireplace, antique soaking tub, and much more.

Whether you’re looking to shower under the stars, find some fresh clams, relax by the fireplace, or have fun with friends, you’ll find it here.

Location: Cape Cod, Massachusetts
Vrbo Rating: 4.8

2. Octagonal Treehouse (Wareham)

Credit: Airbnb

From the moment you see this treehouse and its unique construction you will be enchanted. Sleek and modern outside and in, this abode promises a unique and comfy stay that you won’t soon forget.

This treehouse offers stunning views of the nature around it with its multitude of floor to ceiling windows. Plus, with its unique octagonal shape, you’ll have a great view from anywhere in the house. The treehouse is located on seven acres of private forest, so no need to worry about privacy either.

The interior also has plenty to enjoy while looking out at the surrounding forest. A wood-burning fireplace serves a centerpiece in the living room. A fully outfitted kitchen is available, as well as a large relaxing living area.

Outside you’ll have access to a deck with a modern firepit and outdoor seating. The surrounding area also has plenty of places to walk and upper Spectacle Pond a short walk away.

This uniquely shaped treehouse serves as a perfect homebase to explore the area or for relaxing. For those that might find themselves inspired to work by the beauty of their secluded trip, there is also Wi-Fi included.

Location: Wareham, Massachusetts
Airbnb Rating: 4.94

Related Read: 20 Best Hiking Trails in Massachusetts

3. Mink Cove Treehouse (Wareham)

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This treehouse looks like something straight out of a fairy tale. Nestled in the treetops, 12 feet off the ground, and accessible by a suspension bridge, Mink Cove is a perfect for guests looking for adventure. High up in the trees you’ll have lovely views of Mink Cove and Buzzards Bay.

 Across the suspension bridge you’ll have access to a partially covered porch. This is the perfect space for watching the sky and sipping on your favorite drink.

The treehouse is also located adjacent to miles of trails, so you’ll plenty of opportunity to reconnect with nature. Outside you’ll also have access to an outdoor shower to wash off after your adventures.

Inside, the whimsical construction continues. Wooden all around with a cozy living area and a kitchen perfect for making food on the go.

The sleeping area is up a very narrow spiral staircase. Here you’ll find a double bed and a twin bed up in a loft space. This quaint little treehouse is perfect for a couple or duo of friends looking to disconnect and enjoy nature.

Location: Wareham, Massachusetts
Airbnb Rating: 4.94

4. Modern Treehouse in Truro Hills (Truro)

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Spacious, modern, and equipped with every comfort of home, this treehouse is an ideal getaway for a family or group of friends. The space has multiple bathrooms and bedrooms, a large living area, and plenty of other amenities for a comfortable stay.

 The kitchen is large and fully outfitted to create delicious meals for everyone in your visiting party. There’s even a dishwasher, making cleanup quick and easy. Outside there is also a Weber gas grill if you’re looking to enjoy a meal together on the deck.

The deck also offers a stunning view of Truro Hills and Cape Cod. Outside you will also have access to an outdoor shower, perfect for washing off after exploring the area.

With such a large space filled with activities and comforts, this is the perfect place to disconnect while not having to give anything up. Plan a trip with a family or group of friends for an unforgettable stay.

Location: Truro, Massachusetts
Vrbo Rating: 4.9

Related Read: 34 Best Romantic Getaways In Massachusetts

5. The Pondhouse (Ashfield)

Credit: Airbnb

When looking for a rustic, cozy, and magical stay in the wilderness, The Pondhouse is one of a kind. The Pondhouse is unique, so it might not be for everyone. However, those looking to have a close encounter with nature in a glamping setting will not be disappointed by this space.

The Pondhouse sits nestled among greenery by the titular pond, and you will always have full view of this nature. The Pondhouse is completely screened in. This means you’ll get to enjoy cool breezes and the sounds of nature all around you.

It’s unique screen constructions gives guests a closeness to nature unlike any other place, without having to worry about bugs. Plus, although the cabin is focused on nature, it still manages to offer a very comfortable interior with several amenities.

Inside you’ll find a bed, couches, and a comfortable living area, perfect for relaxing and enjoying the view. Outside you’ll also have access to a composting bathroom, sink, outdoor shower, and fire pit.

This makes The Pondhouse self-contained and perfect for disconnecting. Enjoy a simpler time and recharge in this truly unique accommodation.

Location: Ashfield, Massachusetts
Airbnb Rating: 4.92

6. Enchanted Tiny Tower (Lee)

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Another storybook stay waits for you in this enchanted tiny tower. Immediately distinct from the outside, this French country inspired, whimsical, wooden structure is the perfect homebase for a romantic retreat.

This unique two-story tower sits in the heart of the Berkshires. Surrounded by nature on 4-acres of explorable land, you’re sure to decompress here.

Wander through gardens, past bubbling brooks, and through the woods. Encounter wildlife in their natural habitat and reconnect with nature.

Inside the tiny tower you’ll find a cozy and well-appointed interior. You’ll find everything you need inside from a kitchen with all the tools to make a meal, to comfortable living area, and more.

While not technically a treehouse, this tower’s construction and views will still give you what you’re looking for. Plus, with Wi-Fi, TV, and games available, you’ll be comfortable you’ll also have everything you need at your fingertips.

Location: Lee, Massachusetts
Airbnb Rating: 4.95

7. Treehouse Farm Stay (Rehoboth)

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For those looking for an off the grid stay, this treehouse might just be what you’re looking for. Here you can enjoy the comfort of a rustic, yet spacious accommodation high in the trees, with great views of the nearby farm. Enjoy the sounds of nature and the friendly farm animals.

This treehouse offers you the chance to disconnect from the hustle and bustle of everyday life and go back to a simpler time. Enjoy cool breezes as they come through the open windows, warm up with the wood stove.

Nearby to the main structure you’ll have access to a composting toilet, outdoor bath by the pond, and a charcoal grill. The treehouse is also located near several great restaurants. Enjoy a warm meal before taking a hike around the area.

Location: Rehoboth, Massachusetts
Airbnb Rating: 4.91

Related Read: 20 Best Clear Water Beaches in Massachusetts

8. Magical Yurt in the Woods (Williamsburg)

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Another unique and cozy stay perfect for those looking to unplug, can be found in this magical yurt in the woods. The wood stove inside also makes it a perfect low-key retreat destination for any time of the year.

While the yurt may be rustic and minimal, it still makes the most out of its space. Inside you’ll find a full kitchen, a spacious and comfortable living space, and a private entrance to a full bathroom. You can feel disconnected while still maintaining the comforts of home.

This is especially ideal for those looking to book a longer stay. There’s even a discount if you choose to do so. Those looking to find time for themselves to read, relax, hike, and decompress will feel right at home in this yurt.

Location: Williamsburg, Massachusetts
Airbnb Rating: 4.87

9. Serene Berkshires Cabin (Otis)

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This spacious and luxurious cabin in the trees is packed with amenities for a modern stay. With enough room to sleep up to eight in its 1727sqft, this cabin is ideal for a trip with the whole family or with friends.

It’s cozy, well-appointed interior and proximity to outdoor activities will have something for everyone. Hike the Appalachian Trail, go fishing, or relax inside by the wood burning stove.

During the winter the area transforms into a winter wonderland. Nearby will be plenty of options for skiing or fun family snowball fights. You can let loose, knowing you’ll have a cozy homebase to return to.

Enjoy woodland views, roasting marshmallows over the fire pit, and a screened-in porch as well. Whether you’re looking to relax and decompress or get out and have some fun, you’ll find it here.

Location: Otis, Massachusetts
Vrbo Rating: Unrated

10. A Frame in Sherwood Forest (Becket)

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Those looking for a humble, rustic, and cozy getaway will feel right at home in this quaint A-frame. Don’t let its diminutive size fool you though, this accommodation has plenty to offer and room enough to sleep up to five.

Plus, it sits on a secluded lot of forest, so you and your guests can enjoy your visit in private. Take a hike around the area or head down to the lake nearby. Here you can go fishing, swimming, or just enjoy relaxing by the water.

An added bonus of this accommodation is that while it is secluded, you will always be only a short drive from loads of activities. Head into town to sit at a restaurant, go shopping, or hear some live music.

Location: Becket, Massachusetts
Vrbo Rating: 4.9

Related Read: 60 BEST Things To Do in Salem, MA

11. Log Cabin on Lake Pontoosuc (Lanesborough)

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A classic construction straight out of your childhood toys is waiting for you at this log cabin. Built in the classic Lincoln Log style, this spacious accommodation offers a secluded and comfortable stay filled with activities. Hidden away in three acres of private woods, here you can enjoy the seclusion of the forest and beautiful views of the lake peacefully.

Get out on the water with a canoe or kayak. Decompress and sit in hammock in the waterfront gazebo. The cabin is also strategically located to offer quick access to civilization while still offering seclusion. Inside you’ll have access to a well-appointed kitchen, tv, Wi-Fi, and more.

With the space to fit up to 5 guests, this cabin is great for group outings. The perfect blend of modern and classic are waiting for you all at this cozy cabin.

Location: Lanesborough, Massachusetts
Vrbo Rating: 4.9

12. Gingerbread Treehouse (Lee)

Credit: Airbnb

This unique accommodation promises to give guests a fairy tale experience. It’s distinct wooden construction sits nestled in four acres of land filled with various landscapes, offering a beautiful stay inside and out.

Outside you can explore the private land. Walk over brooks on stone bridges, head down to the lily pond, walk through the forested area, or enjoy the lovely garden paths. There’s also plenty of nearby trails, for those looking to hike.

The abode also sits close to several Berkshire towns. This is great for guests that are also looking to explore a cityscape, eat at restaurants, or do some shopping on their trip.

Inside you’ll find a cozy living area filled with plants and a second story tower area. The tower area has a decent kitchenette, an eating area, bath, and more. Head up another winding staircase to reach the bedchambers with a lovely view of the area.

Location: Lee, Massachusetts
Airbnb Rating: 4.99

13. Double Treehouse (New Marlborough)

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This treehouse is perhaps one of the most visual distinct on this list. It’s made of two individual buildings connected by an elevated deck. This double treehouse also brings the beauty of nature into itself with the live tree poking through the center of its construction.

The double treehouse offers a humble, rustic retreat into the forest, while still being close to the city. Take a hike through nature, or head into Great Barrington for a meal and some shopping.

Anyone looking for a premiere glamping experience will find exactly what they’re looking for in this abode. Disconnect and enjoy nature while knowing that you’re still close to civilization if you need it.

Location: New Marlborough, Massachusetts
Airbnb Rating: 5.0

14. The Writers Retreat (Orange)

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Breathtaking views of Tully Pond and Tully Mountain are waiting for you here in this cozy salvaged barn. Sustainable resources went into every aspect of the design and construction of the abode to make a comfortable and green stay.

It’s outfitted with all the modern comforts of home from a washer and dryer to a TV, to running water, and more. You’ll have everything you need for a comfortable stay and all the views of nature to inspire.

Enjoy mountain and lake views with a cup of coffee, get in a kayak out on the water, or sit at the dedicated workspace. This quaint treehouse is everything you could ask for from a retreat.

Location: Orange, Massachusetts
Airbnb Rating: 4.91

15. Hilltown Cabin Hideaway (Chesterfield)

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This cabin hideaway sleeps up to four and offers a scenic and tranquil visit for every guest. Get a taste of the simple country life without having to give up the comforts of your modern home. Enjoy everything this area has to offer, knowing you’ll have a great homebase to return to.

Inside you’ll have access to full bath, kitchen, laundry, and all the basics of a household. The secondary building serves as a bunkhouse for additional guests. This makes this little hideaway perfect for small groups.

Outside you’ll have access to a multitude of outdoor activities. In the summer you’ll have the choice of several waterways. Go fishing, angling, swimming and more. The space is also near several great trails.

Location: Chesterfield, Massachusetts
Airbnb Rating: 4.97

16. Freda Rose Cottage (Westhampton)

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Those looking for a humble stay without all the bells and whistles will find exactly what they’re looking for in the Freda Rose Cottage. This low-key space is ideal for disconnecting and enjoying the beauty of the area.

The cottage’s proximity to the water makes it great for sitting out on the dock, swimming, or taking a canoe out on the water. The cottage even comes with a canoe specifically for this. Outside you’ll also have access to a firepit and a deck for relaxation.

Another plus is that while the cottage is secluded, it sits only 15 minutes from several town centers. So, you can either prepare a meal in the well-equipped kitchen or head into town for a prepared meal.

Location: Westhampton, Massachusetts
Airbnb Rating: 4.94

17. Berkshires Log Cabin (Washington)

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Get lost in the tranquility of the Berkshires in this modern and spacious cabin in the forest. Located on private land, the cabin allows for a quiet getaway while still remaining close enough to civilization for the essentials.

The cabin comes with a comfortable open concept living and dining space, perfect for enjoying the company of up to six guests. Soak in the clawfoot tub, watch some tv, or go up in the loft for a nap. There’s also fiber optic Wi-Fi for those that need to stay connected.

Outside you’ll have access to an outdoor shower, picnic bench, and room to walk around. This cozy wooden structure is a great place to enjoy the peacefulness of the Berkshires with friends and family.

Location: Washington, Massachusetts
Airbnb Rating: 5.0

18. The Bacchus Cottage (Tolland)

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This private and homey cottage, offers a spacious and cozy stay for up to five guests. Walk through a blueberry meadow to the beach, relax in the airy interior, and enjoy all the comforts of home.

The Bacchus Cottage everything you and your guests will need and much more. Located in Wildwood, a private, year round community, you'll have access to plenty of pristine outdoor activities.

Golf, windsurf, sail, play tennis, or engage in any number of other activities offered by the community. There is sure to be something for everyone. There's also restaurants and other attractions nearby.

Location: Tolland, Massachusetts
Vrbo Rating: 4.8

19. The Photographer’s Hut (Orange)

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This aptly named treehouse is the twin to the Writer’s Retreat from earlier in the list and offers several of the same comforts.  However, it still manages to have its own charm and character for the careful observer. The house is uniquely decorated with antique cameras and offers gorgeous views of the water to take pictures of your own.

Another unique feature is the hut’s ability to house up to four people. The interior comes with all the modern amenities you could hope for and a comfy living area for all guests. Inside you’ll also find other little bits of character that liven up the space, like the Godzilla shower curtain.

Outside you’ll have access to the pond where you can head out in kayaks. For swimmers, nearby Tully Lake is a great destination. Whether you’re looking for inspiration, or simply hoping for a peaceful escape, this hut is a great choice.

Location: Orange, Massachusetts
Airbnb Rating: 4.92

20. Private Upscale Cottage (Truro)

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This modern upscale cottage is a great escape for those looking to enjoy the outdoors with the comforts of a luxury abode. Its location surrounded by National Seashore make it the perfect destination for loads of outdoor activities.

Head out for bike rides or hikes. For water lovers, there are several ocean beaches mere miles away. Nearby is also the city of Truro where you have access to a whole slew of other activities. Enjoy restaurants, museums, and more.

The interior is also well equipped and spacious. Sleep up to four comfortably and has plenty of amenities to make sure everyone is taken care of. This is a truly luxurious stay that offers fun and tranquility in equal heapings.

Location: Truro, Massachusetts
Vrbo Rating: 5.0

Tobi Miles
Article updated:
July 5, 2024 11:03 AM

Tobi Miles is a University of Florida graduate turned globe-trotting culinary explorer and digital nomad expert. As the founder of "Bytes & Bites," he combines his passion for international cuisine with practical advice on remote work, inspiring others to experience the world through food and cultural immersion. With 32 countries under his belt and a knack for uncovering hidden culinary gems, Tobi is redefining the intersection of work, travel, and gastronomy for a new generation of adventurers.

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