The 8 Most Magical Treehouses in Massachusetts

Massachusetts might be best known for its history and seafood, but it’s also full of natural wonder and whimsy.

Believe it or not, despite being home to the metropolis of Boston, the Bay State is actually the eighth most forested state in the country, which rental hosts have taken full advantage of.

Massachusetts forests, like most in New England, are full of oaks, maples, beeches, and birches. And with such gorgeous wildlands, no trip to the state would be complete without staying in them. Whether you want a place that is only steps from the beach or nestled into a mountainside, you’ll find the perfect getaway in the list below.

1. Mink Cove Treehouse

Why you should stay: For a cozy space with views of the cove.

• Nearest town: Wareham
• Sleeps: 2 guests
• Minimum Stay: 2 nights
• Rates from: $144/night

While everyone else might be headed to the Cape for the weekend, avoid the traffic (and the crowds) at the Mink Cove Treehouse. Located only three miles from the town of Wareham, you’ll feel like you’re worlds away. You’ll walk across a stunning suspension bridge to your home away from home and settle in.

At the treehouse, sip wine in one of the Adirondack chairs while watching the sunset, grab a good book and lounge on the hanging bed upstairs, or rinse off in the outdoor shower. Use the house as a jumping-off point to tour the area or never leave the secluded comfort of the woods. Either way, you can’t go wrong.

2. The Treehouse

Why you should stay: To lounge on the deck and take in all the nature around you.

• Nearest town: Truro
• Sleeps: 8 guests
• Minimum Stay: 5 nights
• Rates from: $461/night

There’s no reason to sacrifice luxury when staying in a treehouse and this Truro Hills abode is proof. Although its name is “The Treehouse”, it isn’t technically one. Rather, it’s a cabin on stilts that weaves its way through the trees. Windows flank most of the walls inside the house illuminating it with natural light.

The large kitchen and two (that’s right, two) full-size refrigerators also make this property perfect for hosting parties and reunions. The real highlight is the giant deck area that overlooks the valley below where you and your guests can enjoy a relaxing afternoon and stargazing when the sun goes down.

3. Berkshire Treehouse

Why you should stay: It’s off the grid but still close to town.

• Nearest town: Great Barrington
• Sleeps: 4 guests
• Minimum Stay: 2 nights
• Rates from: $199/night

Reminiscent of a witch’s cottage, this treehouse in the Berkshires could’ve been plucked straight out of a fairytale…but don’t worry, there’s no creepy old woman with warts luring children to her oven. Instead, the homey space reels you in with its whimsy and magic. The large tree that juts up through the center gives the house an ethereal feel. And yet, the house is as sturdy as can be.

Whether you are in the process of writing your first novel or currently a Picasso-in-the-making, this home is ideal for churning your creative juices. One thing to note, the property has no running water. It’s a true glamping experience to get away from it all.

4. Cape Cod Getaway

Why you should stay: Because there’s a private beach!

• Nearest town: South Wellfleet
• Sleeps: 8 guests
• Minimum Stay: 4 nights
• Rates from: $825/night

No need to bring the beach gear, the hosts of this incredible Cape Cod home have you covered. When you stay here, you have full use of the boogie boards, kayaks, and more! You don’t even have to get in your car to hit the beach. There’s a private one accessible over a cute footbridge just minutes from the house.

After a day in the sun, rinse off with the outdoor shower so you don’t drag in any sand. Then make a meal in the oversized kitchen to refill your energy for another beach day. While this isn’t technically a treehouse, the third-floor decks and overlooks sure make it feel like one.

5. Lakefront Treehouse

Why you should stay: The sunsets are unreal from the lakeside deck.

• Nearest town: Monterey
• Sleeps: 6 guests
• Minimum Stay: 4 nights
• Rates from: $284/night

It doesn’t get much better than mountains and a lake, yet this Berkshire treehouse surpasses expectations. The home is simple and does not need embellishments. The beautiful surroundings are enough to make a stay here spectacular.

Spend your days hiking around the area or using the provided kayaks and canoes on the lake (which is conveniently right out your door). Then end your day with a drink on the deck or in the three-season room for those chilly nights.

6. Timberdoodle

Why you should stay: It’s a stunning New England-style home…built into the side of a hill.

• Nearest town: Great Barrington
• Sleeps: 6 guests
• Minimum Stay: 7 nights
• Rates from: $315/night

Although this isn’t technically a treehouse, Timberdoodle is built with nature in mind, so it might as well be one. It’s the perfect basecamp for any outdoor adventure. For winter stays, it’s only a few miles from Catamount Ski Resort and Ski Butternut.

For those who stay during the warmer months, you’re in the heart of the Berkshires and close to tons of hiking trails and state parks. Or, you don’t have to leave the property at all and can enjoy the peace and quiet of the home. There is no nearby light pollution and the woods are filled with plenty of wildlife, like bears, foxes, owls, and hawks.

7. Enchanted Tiny Tower

Why you should stay: It’s a place where you can write, read, and live out your fairytale dream.

• Nearest town: Lee
• Sleeps: 2 guests
• Minimum Stay: 2 nights
• Rates from: $199/night

Play Rapunzel in your real-life fairytale while staying at the tower on the Santarella Estate. There are plenty of windows to choose from where you can let down your long hair. Or, you can play Sleeping Beauty in the four-poster bed complete with sheer curtains. If a warrior princess is more your style, hiking the surrounding woods will have you feeling daring and adventurous.

But, if you’ve already found your Prince Charming, the seclusion and whimsy of this place are great for a romantic getaway (not to mention perfect for Insta photos).

8. Quaint, Lakefront Treehouse

Why you should stay: To escape the daily grind and immerse yourself in nature.

• Nearest town: Great Barrington
• Sleeps: 2 guests
• Minimum Stay: 1 night
• Rates from: $185/night

This cozy and quiet treehouse has very little when it comes to modern amenities…but it doesn’t need them. Between the hanging bed and glass walls covered with wisteria plants, the space is meant to be savored and enjoyed without distraction.

The corrugated roof is ideal for those rainy days when you can snuggle inside and listen to the rain. But on nicer days, grab a stand-up paddleboard and float out on the lake that’s just a few steps from your door. Or, grab your favorite book and read under the dappled sunlight coming through the trees.

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