Autumn is the perfect time to get cozy.
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As temperatures drop, forests across the country transform. Leaves slowly die in a beautiful display, ushering in the start of the harvest season. It’s a time to visit pumpkin patches, sip on spiced drinks, and cuddle up with loved ones in front of bonfires.
And what better place to do all of the above than while staying at a cottage?
In New England, no less?
While watching the leaves change is a classic pastime across the US, New England has a reputation for its stunning displays. And Massachusetts, with its towering forests and stretches of unspoiled land, has more hidden escapes than you’d expect to find in the 7th smallest state.
Whether you’re looking to head on a romantic and cozy couples retreat or simply drift back into the embrace of Mother Nature, Massachusetts should be in your travel rotation.
Looking for the perfect cottage escape to enjoy fall foliage in Massachusetts? Start with this list. It’s cottage-core… Massachusetts style.
Family adventure chalet
Otis, Massachusetts (Berkshires)
There’s a lake, kayaks, and a sauna—need I say more?
Well, I’d actually like to rave about the thick woods surrounding the house. They’re a Hollywood-caliber backdrop for all the outdoor activities you’ll want to enjoy in the fall.
There’s a fire pit for bonfires and a sauna for warming up. Plus, extras like a grill and even a pizza oven. The interior also reflects the rental’s moniker of a chalet—you’ll notice tons of wood features that feel purely Alpine.
Cozy lakeside cottage retreat
Groton, Massachusetts
This lakeside retreat truly is a remote oasis. But the home was remodeled in 2017, which means guests get all the modern amenities and finishing touches of a newer rental.
What I love most here is all the outdoor space.
The dock leads to a lovely pond, which is surrounded by all the outdoor features you’ll need to soak up the autumn beauty. Best of all, there’s a fire pit that perfect for toasting s’mores while enjoying the crisp air.
Farm Stay at Historic Ski Lodge
Holden, Massachusetts
No, you’re not in Giverny. This historic ski lodge might look like the stuff of rural France, but it’s recently been converted into a barn stay.
Though you aren’t immediately sheltered in the trees, you’ll have a spectacular view of the surrounding woodlands. It’s ideal for evening strolls and soaking up the views from the back patio.
Inside, you’ll find plenty of antiques, adding to its historical allure.
House on Otter Pond
Tolland, Massachusetts (Berkshires)
Like other lakeside, autumn-centric rentals, guests have kayaks and canoes ready to take out on the water. And while Otter Pond might sound sparing, the body of water looks more like a lake.
And who doesn’t like to soak up an autumn dreamland from the water?
On top of the scenic surroundings, the house is warmed by a wood-burning stove, which turns any autumn adventure into a cozy, romantic retreat.
Cottage with Private Beach
Ashburnham, Massachusetts
This dark-wood cottage is remote and located right on a private beach.
It’s sheltered by a stretching, healthy woodland, which offers a private way to soak up the stunning foliage. I’d personally spend my time at the fire pit by the lakeside.
But even if you’re indoors, there are enough windows in this cottage to provide an endless view of the natural wonders outside. Just keep in mind that this stay is slightly more rustic than others on this list.
Hidden Gem Barn
Acton, Massachusetts
Located only thirty minutes from Boston, this is the most accessible fall cottage selection on the list. The barn is located near the host’s main home, which means it might not be the best for those seeking total privacy.
That being said, guests have declared this spot a ‘home away from home’ thanks to the hospitality of the hosts. (That’s always a huge plus for me.)
To top off this wooded escape, there’s also a stunning patio that lets you immerse yourself in the forest as it transforms in autumn.
