The Best Airbnbs in and Around New England to Soak Up the Foliage This Fall

These spots will provide an autumn peep show unlike any other, plus other rad amenities to enjoy when the hiking boots come off.

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Autumn gets a bad rap for being the season of “basic”…everything. Cozy sweaters, pumpkin patches, apple picking, and, of course, the both dreaded and beloved PSL. But, people: basic isn’t always bad! Especially when it’s accompanied by crisp air that makes you want to breathe, shorter days that beg for roaring fires and spiked hot cider, and a peaceful quiet that overcomes nature as the landscape transforms from dense to dormant during a majestic journey that brings with it golds, oranges, and reds of autumn—better known as fall foliage.

New England (and the surrounding area) is famous for being the best spot to appreciate this bizarrely beautiful transformation of life to death, especially if you hit particular locales during their peak color-changing period. Craving a getaway that calls for long walks accompanied by the sounds of leaves crunching under your feet while surrounded by some amazing leaf-changing action? These Airbnbs will provide an autumn peep show unlike any other, plus other rad amenities to enjoy when the hiking boots come off.

A converted barn near Woodstock with views of Overlook Mountain

16 guests/$1,414 per night

This converted barn dates back to the mid-1800s, but rest assured, it’s been updated with modern amenities (though charming rustic details are still visible throughout). The house sleeps 16, and many of the bedrooms have views of Overlook Mountain. For even more views after you get out of bed, there are enormous windows, a screened back porch (with a clear ceiling for maximum sunshine and star-gazing enjoyment), and a patio with an eight-person hot tub. The house sits on 16 acres of land where you’ll discover 19th century stone walls, two ponds, a creek, and a couple of hammocks—because nothing makes you need a nap in a hammock like staring at fall foliage all day.

What guests say: “What a sanctuary! Rob's house is one of the loveliest houses we've ever stayed at. Big, light, and thoughtfully furnished, with incredible views on a fantastic piece of land. A quick drive away from Woodstock but incredibly private. We enjoyed cooking in the wonderfully appointed kitchen, soaking in the hot tub under the stars, and exploring the forest, streams, and pond on the property. There's so much to discover!”

An octagonal glass treehouse in the Berkshires

4 guests/$350 per night

Airbnbs with one cool quirk are exciting on their own, but an Airbnb with three cool quirks? That’s more excitement than any leaf-centric vacay has seen in a while. This home in the Berkshires (20 minutes from Great Barrington) is a treehouse (!), made of glass (!), and eight-sided (!!!!!!!!). Thanks to the fact that it’s made of glass, it offers unobstructed views of the reason you’re there (the trees and their leaves). Take those in during the evening while grilling on the spacious deck, and then when the sun goes down and with it, your raison d’etre, gather around the firepit or wood-burning fireplace with a cocktail in hand.

What guests say: “Unique, private, and relaxing location. Close to lots of great hiking trails and the small town of Great Barrington for some local shopping and dining. The treehouse was a great place to relax and enjoy a book by the firepit on the deck or play some games around the indoor fireplace. Cozy beds and a modern style complete this fun house!”

A renovated farmhouse with historical details and a charming pond

8 guests/$457 per night

This 1793 farmhouse has been renovated to include 21st century amenities, but it is not without unique 18th century details, like wide-timbered wood floors, exposed beams,  and tiny nooks throughout. It sits on 16 acres of well-maintained land that truly lives its best life in the autumn when you can take leisurely walks to the pond or just sit on a stone bench and take it all in. (There is a swimming pool, but it’s only open during the summer.) One of the bedrooms is in the attic, which seems like it would be the room someone gets “stuck” with, but it actually may be the coolest room in the house because of all of the wood and the cozy reading nook. Also, like any good house meant for relaxing, there’s a hammock for afternoon (or morning—no one is judging here) naps.

What guests say: “This house is living history, and the grounds are absolutely stunning. We stayed during fall, and the trees were absolutely stunning on the property. We fished in the lake, enjoyed the fireplace, and loved the history. Still close enough to town to go out for dinner or groceries.”

A modern glass and wood cabin with a heated swimming pool

4 guests/$450 per night

If you want a cabin vibe without the creaking floors and dusty corners, this sleek dwelling near Rhinebeck is for you. While there, you’ll have access to the 3.5 acres of land, but if you don’t feel like wandering to find your fall colors, you’ll also be able to take in the wooded view from the 360-degree views (glass is an amazing thing!) and the swimming pool that is heated year-round. Other cool amenities include an orb fireplace, outdoor shower, solarium cottage in the woods with a wood stove and a bed, hammock (natch), heated cement floors throughout, and deep soaking tub. 

What guests say: “Absolutely gorgeous. Coming up the driveway with the lights guiding us, inviting us, made for a lovely welcome that felt like a hug. Opening the door (easy) and stepping into this oasis of a space and it's like weights you didn't know you carried are lifting. Getting into the heated pool first thing on a crisp-ish morning relieving your tense back quicker than a massage. And take it from me, you want there to be a rainy day because that fireplace will crackle even sweeter. 10/10 recommend.”

Luxury cedar log home on the Sunday River

16 guests/$732 per night

Newry, Maine has a population of fewer than 350 people, so this is an ideal location if you truly want to get away from it all and not get a single noise complaint. It’s also the site of Maine’s worst Cold War aircraft crashes and a B&B where four people were murdered in 2006, but that guy is in prison for life, and anyway, this isn’t a B&B; it’s a private home! And it’s not just any private home; it’s a private home located directly on the Sunday River (great for trout fishing) and with views of the tree-covered (you know what that means!) Sunday Slopes. Sit around the fire pit in the gorgeous gazebo on the main deck one night and the fire pit by the river another. There’s also a hot tub for six to eight, a sauna for detoxifying after late nights, and a pool table.

What guests say: “If you are planning a trip to the Sunday River/Newry area, then look no further than Rediker Retreat! This house has it all and then some. From the gorgeous log cabin style to the open concept living areas, beautiful indoor fireplaces, plenty of sleeping areas, two outdoor fireplaces, sauna, waterfall steam shower, hot tub, and amazing views of the river and mountain, you won't actually ever want to leave this gem in the mountains!”

A former Girl Scout lodge in the Catskills

7 guests/$379 per night

This Adirondack lodge in the town of Catskill proper was originally a camp lodge for Girl Scout church services and stage performances. Today, it’s been completely renovated into a spacious three-bedroom cabin with a fully-stocked chef’s kitchen, massive stone fireplace, windows throughout that look out at the forest and the Catskill Mountains, and a covered porch for morning coffee and afternoon beers. It’s also close to tons of hiking trails, and Saugerties, a small town with fun bars and restaurants, Woodstock, and Hudson (if you’re more into wine and cheese than the burgers and beer you’ll find in Saugerties). Oh, and if you have a hankering to reenact those Girl Scout performances? There’s a baby grand piano just waiting to be played.

What guests say: “The perfect mini escape from the city. The home is impeccably decorated, very clean, and well-stocked with everything you need. The location is great for some of the best hiking in the Catskills. We will definitely be back!”

A historic icehouse surrounded by 900 acres of private wilderness

4 guests/$259 per night

Originally built to store blocks of ice that were cut from nearby ponds in the winter to use in the summer, this 19th century property is now a very cozy mix of old-meets-new, perfect for “simple cabin living.” The kitchen has everything you need, including a waffle iron and an ice cream maker (because what are waffles without ice cream?) and there’s an outdoor grill for cookouts and dinners looking out at the Adirondack’s High Peaks. But the best part is that you’ll be surrounded by hiking trails, babbling brooks, and open fields that no one has access to but you. 

What guests say: “The icehouse was amazing. It is a perfect location for anyone seeking to connect with nature and to enjoy some peaceful silence. The cabin is super cozy, with its many blankets, fireplace, and architecture. The kitchen is fully equipped for home cooking. The trails around the house are beautiful to walk and offer many different views of the Adirondack high peaks. Sugar house creamery is right down the road where you can support a small local farm by buying their high-quality cheese, milk, eggs, meat, baked goods, and more.”

Modern home on 800 acres in the Appalachian Mountains

6 guests/$550 per night

West Virginia probably isn’t the first place you think of when you dream of a fall escape, but this mountain home will convince you otherwise. Not only is it right in the heart of the Appalachian Mountains (meaning: plenty of hiking and biking trails covered in those leaves you’re craving so badly), it’s on a private lake stocked for fishing (and playing thanks to a canoe, kayaks, and paddleboards), and there’s an infinity-edge pool, hot tub, and sauna. Into disc golf? There’s a course on the property.

What guests say: “Reality is as good as the pictures. The house is great, but the pool/hot tub/lake were phenomenal. This place really is off the beaten track; there's truly nothing else around. And there is no wifi, which is a little tricky in these modern times. But a wonderful place to unplug and enjoy some relaxing time with family. You won't be sorry you booked!”

A historic grist mill perched atop Mill River waterfalls

4 guests/$303 per night

You could see this romantic and totally unique getaway on HGTV, Netflix, or in Architectural Digest, or you could experience it for yourself. If you choose the latter, you’ll be treated to a stay in a 1778 grist mill that features original elements like hemlock grain bins and ladders, and a getaway that only a few people will ever be lucky enough to experience. The Mill comprises four narrow stories that include two chained and cantilevered river decks overlooking Mill River's 150-foot carved waterfall (probably not ideal for those scared of heights, but perfect for those who want to take it all in with their beverage of choice in-hand). The entrance to the Mill is a covered bridge (does it GET more New England than that?), and there’s a path that runs along the river—both perfect for those fall foliage photos. There’s also plenty of hiking nearby and, if weather permits, swimming in the river, which is apparently Vermont’s warmest.

What guests say: “This space is truly a must-visit. Wrapped in nature, historical charm, and hosted by incredible people that want to make your stay as special as possible. The Mill is comfortable, relaxing, and full of artistic and historical expression. The sound of the river swallows you into sleep and wakes you in the morning. Tons of outdoors to explore around the Mill.”

A modern cabin in the Catskills

4 guests, $352 per night
Described as "small but efficient," it'd be tough to feel cooped up in this quiet cabin considering its sweeping Catskill views and a deck that essentially functions as a second living room (just imagine sipping your morning coffee or winding down with some wine out there). It's a cozy spot that pairs country charm with modern amenities (indoor/outdoor Sonos speakers and a Nest thermostat-controlled fireplace), and also has everything you need to cook up a storm, including a grill. Plus, if you're in the mood to get up close and personal with the outdoors, it's only a short drive to popular hiking spots like Vernooy Kill Falls. 

What guests say: "This is a wonderful little hide-away, perfect for a 'time out,' away from everything. It's exactly as described, very stylish, in the middle of beautiful nature with gorgeous views and with complete silence (apart from the bird song)."

A historic schoolhouse perched in the Green Mountains

6 guests, $303 per night
Looking out over a sprawling fourth-generation organic farm, this newly renovated 800 square foot two bedroom schoolhouse gets insane views of the Green Mountains from literally every direction. Take in the vista from the deck with your morning coffee, or sit by the fire pit and watch the sun go down. If you feel upping the relaxation ante, there's also an adjacent deck equipped with both an on-site sauna and hot tub, either of which makes for a spectacular star-gazing spot at night.

What guests say: "Amazing place -- book it now and however amount of time you are pondering about staying -- add at least one more day! They have put a lot of thought and work into making this home truly feel like a home away from home for guests -- many thoughtful touches and the views are divine."

A rustic retreat in the Berkshires

8 guests, $300 per night
As if plucked from the pages of Architectural Digest, this stylish retreat is centrally located in the Berkshires between the towns of Stockbridge, Lenox, and Lee, serving as an ideal home base for a chill weekend away in the thick of leaf-peeping madness. With enough room to sleep eight, it's can likely accommodate your whole crew, but still feels cozy thanks to quaint touches like natural wood paneling and an indoor fireplace. When you feel like exploring, you've got plenty of options thanks to some standout nearby restaurants and hiking trails, plus museums like the Clark Art Institute and MASSMoca that are less than an hour's drive north.

What guests say: "An interior designers dream home well equipped with everything you could possibly need for your stay. Great location close to all the local townships whilst offering complete peace and tranquility."

Treetop views in the Vermont National Forest

9 guests, $217 per night
If you're looking for seclusion in the mountains, this spacious three bedroom retreat has you covered. It sits on two acres in the hills and features a huge deck that stretches the length of the entire home, providing a stunning 180-degree view of the Green Mountains (which flourish with color in September and October). Although the built-in stone wood-burning fireplace will make it hard to want to leave its confines at all, if you do feel like exploring, the quaint downtown of Rochester is just a few minutes quite literally down the road. 

What guests say: "This home is absolutely incredible. Truly the middle of nowhere and so unbelievably gorgeous. Sweeping mountain views, a very well equipped kitchen, and multiple bathrooms - could we ask for anything more?"

An upscale escape in Maine

4 guests, $269 per night
Although you don't need any excuse to visit Portland in the fall (it's particularly great just after peak tourist season), this modern post-and-beam cottage is itself worth the trip. Situated about 20 minutes from the tiny coastal city, you're close enough to the top-notch restaurants, breweries, and other fun sites in the Old Port to be convenient, but secluded enough to enjoy the tranquility of being tucked away amongst the colorful changing trees. The rustic home -- which has been described by some guests as the "perfect oasis" -- also boasts a couple standout touches like a lofted bedroom and wood stove.

What guests say: "'Can we just stay here forever?' That thought ran through my mind countless times whilst staying at the cottage. I have enjoyed many vacations and yet this little 2 day getaway in the cottage tops them all. We will be back soon enough and would one million percent recommend to anyone looking for a place to stay in the area!"

Daisy Barringer is a freelance writer whose favorite book as a child was the incredibly depressing “The Fall of Freddy the Leaf,” which is exactly what you’re thinking it is. Follow her on Twitter @daisy for more uplifting gems like this one.
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