Love You Some Fall Foliage? These Are the 8 Best Vacation Rentals to Book

Get out there and do some leaf peeping while autumn is still ablaze!

I just love fall—and not solely because it provides the perfect opportunity to show off a new pair of boots and coat. It’s more about the crispness in the air, farmers’ markets bursting with apples, gourds and cider, people being a little nicer to each other on the subway because it no longer a reeks of perspiration—and, oh yes, the hills and valleys ablaze with color. It is the perfect time to plot a little getaway to do some “leaf peeping,” as those quaint Vermonters like to call it, at the brilliant fall explosion.

I’ve rounded up a list of vacation rentals in points far and wide—from the Green Mountains, to the Great Smokies, the Catskills and the Rockies—that are sure to provide a picture perfect autumnal escape. No filter required.  

Stowe, Vermont

New England reigns supreme for fall colors, and perhaps no place is as picturesque as Vermont, which is literally aflame with reds, yellows, pinks and oranges. See the sights while staying cozy in this cabin in Stowe. Tucked away in a little dell at the edge of the woods, it offers mountain views that are sure to be vivid and it comes equipped with all the modern fixins, including an outdoor hot tub and field stone fireplace ideal for nestling. Close enough to Stowe Village that you won’t feel completely cut off from civilization (unless you really want to be). Wind your way there via the Green Mountain Byway for a jaw-dropping presentation of the changing maple, birch and beech trees.

RENT FROM: VacationRentals, from $310 per night, sleeps 4

Mount Desert Island, Maine

Acadia National Park in Maine is renown for its fall display, and this little gem puts you smack dab in the middle of it. But, more importantly, it’s a yurt! Yes, live out your yurt fantasies and blow up your Instagram while ogling spectacular scenery right outside your door. It’s like camping, but with all the conveniences a city girl can’t live without—such as heat, electricity, running water and shelter from random ravenous bears. Located in Southwest Harbor on Mount Desert Island, the yurt is near numerous hiking trails, and Bar Harbor is a short drive away. Leaf peeper pro tip: don’t miss the 27-mile Park Loop Road with its alternating views of the rugged Maine Coast and the dazzling hues of Acadia National Park.

RENT FROM: VacationRentals, from $87 per night, sleeps 4

Woodstock, New York

People like to say the Catskills are the new Hamptons. But I personally like to think of them as Brooklyn with more trees. Either way, the fall display here is extraordinary. Not only that, its proximity to New York means you can count on really good coffee, even in the most obscure of hamlets, and flea markets that are “well-edited” with all the artisanal delights—plus really good people watching at the Phoenicia Diner. Yes, celebs have homes all around this region. So keep your eyes peeled and at the same time don’t let the stars distract you from what you came here for: NATURE! This Woodstock retreat fits the bill. Newly refurbished and heavenly, it has all the amenities, including hot tub, but the true centerpiece is the stunning view from the deck of Ashokan Reservoir and Shawangunk Mountains, which is especially lit up during autumn. Your morning coffee never looked so good.

RENT FROM: VacationRentals, from $288 per night, sleeps 6

Monterey, Massachusetts

Narrow winding country roads, charming picturesque villages and sweeping forest vistas with frolicking white tail deer (and, okay, some bears)—what’s not to love about the Berkshires? And in the fall it is just so darn purdy. Leaf-peepers make the pilgrimage to Jacob’s Ladder Scenic Byway, a 35-mile stretch of road through the southern Berkshires and to the gorgeous Mohawk Trail along the northern end. This lakeside cottage in Monterey is the perfect base for exploration. Situated on nine acres, it provides seclusion and tranquility, but access to all the Berkshires has to offer—Great Barrington, Tanglewood, MassMOCA and other museums are a hop skip away. The Appalachian Trail is nearby for hiking, and the private dock awaits for your moment of zen. 

RENT FROM: VacationRentals, from $163 per night, sleeps 5

Pigeon Forge, Tennessee

Great Smoky Mountains National Park is one of the most popular national parks in the United States and for good reason: it is awe inspiring. The vast diversity of trees here guarantees a trippy display of fall colors, especially in late October and early November when its sugar maple, scarlet oak, sweetgum, red maple and hickories literally glow. This Pigeon Forge cabin has every amenity you could possibly want and views to die for, but don’t! Watch the Smokies change color from the high perch of the deck instead. And if you neglect to take a spin on at least a portion of the famous 469-mile Blue Ridge Parkway, you’re doing it wrong.

RENT FROM: VacationRentals, from $125 per night, sleeps 4

Asheville, North Carolina

Eclectic Asheville is a perfect basecamp for exploring the Blue Ridge Mountains any time of year, but during fall Mother Nature really gets gussied up. Variations in elevation ensure a long and vibrant season, beginning in mid September and ending in November (find a foliage forecast here). Asheville is close to so many stunning scenic drives you might be too blissed out to ever leave your car, but when you finally do you’ll have a nice place to lay your head in this rustic cabin hideaway in Buffalo Mountain. Views abound (as well as the obligatory outdoor hot tub to take them in from, a leaf-peeper essential), and you’re minutes from downtown Asheville, the Biltmore Estate and the many trail heads off the Blue Ridge Parkway.

RENT FROM: VacationRentals, from $171 per night, sleeps 6

Aspen, Colorado

They don’t call it Aspen for nothing. The shimmering tree that grows so abundantly in Colorado explodes into bright yellow in fall, a stunning bolt of color against the majestic Rockies. Popular leaf-viewing spots in the area include the iconic Maroon Bells peaks, Crater Lake and American Lake. Drive the stretch of the Kebler Pass road between Paonia Reservoir and Crested Butte to glimpse the world’s largest aspen forest. Or ride the Silver Queen Gondola to the top of Aspen Mountain for a particularly mind-blowing autumn panorama. Aspen lodging ain’t cheap. Here’s a solution: Bring a crew of friends and make a memorable weekend out of it! This expansive abode in Snowmass Village has six bedrooms and enough hot tubs to make everyone happy. That on-top-of-the-world feeling will be priceless.

RENT FROM: Homeaway, from $600 per night, sleeps 13

Columbia River Gorge, Oregon

On any given day Oregon’s 80-mile Columbia River Gorge can take your breath away. But come autumn, when the maples, ash and cottonwoods start their color show, the spectacle can leave you feeling downright besotted, like when you gaze at something too beautiful to behold (I’m thinking Kit Harington) and you need to sit right down. Sigh, where was I? Yes, drink it in while driving (or rafting) along the Columbia River or hike some of the numerous trails. And when it’s time for your lovesick soul to rest, retire to this luxe log cabin with your own private waterfall along the Rock Creek River. Listen to the lulling rush of water, pop some logs in the fire and pour a glass from one of the local wineries. Kit (and I) would be very happy here.

RENT FROM: Homeaway, from $350 per night, sleeps 2

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