20 Vacation Rentals Perfect for a Fall Getaway (and Yes, You’re Gonna Want to Book ASAP)
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If the back-to-school commercials and the Halloween costume pop-up stores (ugh) haven’t already tipped you off, then we have some news for you: Summer will be over before you know it. We’re all about living in the moment, but we also know that if we want to make the most of fall, we have to start planning now. So while everyone else is blissfully enjoying the ocean (NYC does have some great, underrated beaches), we suggest getting a jump on booking your fall weekend escapes, because now is the perfect time to snag those rentals that were so difficult to lock down during the busy summer season. From a Grecian English manor that’ll rival the Bridgerton family home, to an adult treehouse and mid-century modern artist’s studio, here are 20 fall vacation rentals near NYC (many of which are PureWow editor-approved) that abound with autumn foliage and plenty of fall festivities.
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1. Cloud 9 Lodge (Lake Harmony, PA)
“Situated in the heart of Lake Harmony, Pennsylvania, this home puts you smack dab in the middle of gorgeous foliage come peak fall. My friends and I rented this Airbnb a few years ago and fell in love with the place, from the stone fireplaces to the sprawling downstairs game room. It has huge windows and plenty of outdoor deck space for big groups to relax outside and take in the leaves. Another fun bonus? It’s got a year-round hot tub!” - PureWow senior commerce editor Stephanie Maida
2. Lakeside Retreat (Jim Thorpe, PA)
“I love heading to the Poconos in Pennsylvania come foliage season, and one of my favorite towns in the region is the oh-so-charming Jim Thorpe,” Maida says. Not only is the town center filled with cute shops and eateries (all housed in a smattering of Insta-worthy architecture), but there's a ton of outdoor activities to take part in surrounding it, including hiking trails that take you on a foliage-filled tour of Lehigh Gorge State Park.” Make this peaceful lakeside retreat your homebase, with its generous wrap-around deck and lakefront backyard perfect for lounging around with your friends and family on a long weekend. And if you’re willing to brave the waters, kayaks, peddle boats and a canoe are available.
3. Eastwind Hotel & Bar (Windham, NY)
“If you’re looking for an idyllic weekend upstate that's plucked right out of a Hallmark movie, this is it,” raves PureWow executive managing editor Catrina Yohay. “We stayed in a king suite in the main house and loved its stylish, no-frills, Scandi vibe. The property as a whole feels cozy and inviting. Each morning we’d start the day with a freshly made breakfast complete with scrambled eggs, bacon and mini muffins. After a day of hiking and beer tasting at the local taproom (a stop at West Kill Brewing is a must, to this day it’s still my husband’s favorite brewery), we’d cap off each night with a craft cocktail at the Eastwind bar and lounge while casually playing chess next to a roaring fire. Also, it’s dog-friendly, a major win in my book. We can’t wait to go back and bring our pup along!”
4. Wildflower Farms (Gardiner, NY)
“Secluded and submerged in nature—what more can you ask for?” Yohay raves. “I loved exploring the 140-acre grounds on foot, meandering through the rows of cabins while enjoying the mountain backdrop off in the distance. My favorite morning began with some of the best olive oil pancakes I’ve ever had, devoured at their main restaurant Clay and ended with a trip to the chicken coop to feed the hens (P.S. they love being held!). The service is also unbeatable with each staff member going above and beyond. Sidebar: I had a love affair with the strawberry jam they use in the restaurants and asked if they had jars available for purchase. The kind staffer told me no but that he would see what they could do. Later that day, I came back to my cabin to find three complimentary jars of jam with a personalized note...I mean come on! Top-tier service, without a doubt.”
5. Hotel Lilien (Tannersville, NY)
“Tucked away in the Catskills, this Victorian boutique hotel is so cozy,” says Jillian Quint, PureWow’s editor-in-chief. “There are little nooks everywhere for reading, canoodling or grabbing a quick game of checkers. Although honestly, when I was there mid-winter, all I wanted to do was cozy up by the wood-burning stove.” If you come in the fall, you’ll be in that sweet spot where days are still mildly warm but get chilly at night. Be sure to set aside time to stroll down the historic main street in the afternoon, explore the nature of Catskill Park and Mountain Top Arboretum, then cozy up by the fire pit at night.
6. Urban Cowboy Lodge (Big Indian, NY)
“If you combine the words ‘rustic’ and ‘luxury’ you’ll get the vibe of Urban Cowboy,” says Purewow senior commerce editor Stephanie Maida. “I felt like I stepped into my Yellowstone dreams in the bar and lounge area, which is decked out in Western textiles, wooden accents and even an antler chandelier.” Set smack dab in the middle of the Big Indian wilderness, there will be fall foliage in abundance, which you can enjoy via an idyllic ride on the Delaware & Ulster Railroad or while pedaling a small railcar yourself. Other great places to breathe the fresh, crisp fall air: Big Indian Wilderness, Mount Tremper Trail and Overlook Mountain.
7. Scribner’s Catskill Lodge (Hunter, NY)
With a dog-friendly policy, consider this the best fall vacation rental near NYC for pet owners. According to PureWow fashion editor Abby Hepworth, Scribner’s is also one of the Catskill’s most glamorous hotels. “While the Catskills have an exciting restaurant scene, don’t miss a meal at Prospect, the hotel’s on-site restaurant, which serves delicious cocktails and rustic fare using locally sourced ingredients,” she says. “I also love the outdoor firepits, perfect for making s’mores and watching the [leaves] fall.” There’s plenty to see around the area, too, from Kaaterskill Falls to antique shopping in Tannersville.
8. The Tiny House (Hastings-on-Hudson, NY)
It takes just over an hour by car (or 40 minutes by train from Grand Central) to reach Hastings-on-Hudson, a village sitting on the Hudson River. Rife with foliage that blankets the gently rolling hills, it’s a prime destination for leaf-peeping that doesn’t demand you trek hours out of Manhattan. The Tiny House itself is a charming and quirky little property in an equally eclectic town. Think chickens out back, a hammock, fireplace (and pit) and fun artwork. And if you loved the character of Gilmore Girls’ Stars Hollow, you’ll find that Hastings-on-Hudson gives a similar vibe, from the old fashioned diner and speakeasy to an under-the-radar record store and family-owned hardware store and pharmacy. A perfect place for a stroll in the crisp autumn air, if you ask me.
9. Sleepy Hollow Apartment (Sleepy Hollow, NY)
What better time to visit the legendary Sleepy Hollow than during peak spooky season? Yes, this is *the* Sleepy Hollow—the idyllic town on the Hudson where opportunities for leaf peeping abound. Your first stop? The Sleepy Hollow Cemetery, of course. Who knows? You may encounter the Headless Horseman. But ghosts aside, the town has a lively reputation for going all-out on Halloween, and this cozy apartment is in the center of it all, literally. It’s adjacent to the Rockefeller State Park Preserve, where you can take a hike among the vibrant colored leaves. If you visit in October, you’ll also want to catch Lyndhurst Castle, when the Gothic revival mansion is bathed in candle light.
10. Tarrytown Studio (Tarrytown, NY)
Tarrytown is another village that lives in the literary hall of fame, notably as a principal settling in F. Scott Fitzgerald’s The Beautiful and Damned. While the family was fictional, you can visit the home of a real literary legend: Washington Irving. His historic home, Sunnyside, is a Dutch stone house that sits on a bucolic ten acres and is beautiful in autumn. You’ll also catch stellar views on the Hudson Riverwalk. Picture it: A brisk fall stroll while nibbling on a bagel from the local institution, Bagel Emporium, and watching the sunrise. Seeing as it’s less than an hour from Manhattan via Grand Central, there’s really no excuse not to go. And this little Tarrytown Studio puts you in the middle of it all.
11. The Barn (Tivoli, NY)
If you want to be completely enveloped in nature, head upstate to The Barn, a rustic outpost in Tivoli. With a fire pit, picnic table, pond and creek, it gives you every excuse to be outside, marveling at the changing seasons. In town, be sure to try a scoop of the seasonal apple cider doughnut ice cream at Fortune’s, enjoy a cozy meal at Rojo’s Tapas and Wine and see the Catskills at blue hour from Tivoli Bays.
12. The Hunter Greenhouse (Tannersville, NY)
Come to The Hunter Greenhouse for a breath of fresh mountain air and starry night skies, and a place to cozy up as the temperatures begin to drop. Large windows offer serene views of the forest, with a fire pit on the deck where you can gather around in all seasons. (But autumn, of course, is one of the best times, with mild temps that are *just right* for roasting marshmallows and wearing a down jacket.) The lack of light pollution will allow you to view dazzling fall stars and constellations, including Orion, Aquarius and Capella.
13. Sag Harbor Mid-Century Home (Sag Harbor, NY)
Autumn Hamptons getaway? Yes, please. This fall vacation rental is a mid-century marvel three hours from NYC near the tip of Long Island. Here, soaring 20-foot-tall windows provide a generous view of the fall leaves, and you can reach the village by foot. Start with a doughnut at Grindstone Coffee & Donuts and stroll down the historic Main Street, which dates back to 1745. You should also not hesitate to use Sag Harbor as your base to explore the the tip of Long Island, including “the end of the world” in Montauk. (It’s also a given that you should consume as many lobster rolls as humanly possible.)
14. Cozy Hudson Retreat (Germantown, NY)
As the temperatures get chillier, what better way to usher in fall than with a trip to Germantown? This quaint country home overlooks acres upon acres of bucolic pasture, with the mountains looming in the distance. And, the surrounding area is rife with farm stands hawking everything from dairy products to meat and produce, which you can then prepare in the stocked kitchen. If you really want to get into the fall spirit, hit up the local pumpkin patch, Mead Orchards, which also offers apple picking and a corn maze. The trip isn’t complete without a meal at Gaskins, whose owners, Nick and Sarah Suarez, cut their teeth in many establishments in NYC.
15. High Tea & Hedgerows (Poughkeepsie, NY)
Bridgerton fans, now’s the time to retreat to your country estate, aptly named High Tea & Hedgerows. The charming (and rather palatial) 1840s Grecian-style English manor is 40 minutes from Poughkeepsie, sitting on a sprawling 18 acres. After you’ve taken your breakfast in the farmhouse kitchen, stroll the grounds and gardens as towering oak trees sway in the breeze and colorful leaves rain onto the path. Then, like any proper young society lady, spend your afternoon in the library near the fireplace, or playing the antique piano. All that’s missing is a dashing duke…but who knows? You might just find one here.
16. Zenhouse (Stamford, CT)
Talk about an epic fall vacation rental near NYC. The Zenhouse, located less than two hours from Manhattan, sits on the property of the former studio of American sculptor Gutzon Borglum. (That’s the man who designed Mount Rushmore, FYI.) The guesthouse and pool offer 3.5 acres of tranquility, a pool and tasteful mid-century design. Meanwhile, the city of Stamford is rife with outdoor activities, including the Stamford Museum & Nature Center, Cove Island Park and Mianus River Park. Take advantage of the waning (warm!) days of autumn while you can.
17. North Fork Oasis (Cutchogue, NY)
Autumn in wine country? Name a better fall vacation idea, I dare you. Round up a group of friends (this North Fork property hosts 11) for a weekend on Long Island in the region’s famed gastronomic capital. Large glass sliding doors offer a serene view of trees, fields and vineyards that stretch for miles, and there’s a chef’s kitchen where you can prepare meals from locally-bought produce. As for what you actually came for: Wine tasting in the autumn. Be sure to stop by Bridge Lane Wine, Baiting Hollow Farm Vineyard, Clovis Point Wines and Croteaux Vineyards—just to get you started.
18. Historic Upstate Home (Poughkeepsie, NY)
Venture up to this historic home in Poughkeepsie, where colorful fall foliage abounds and you’re surrounded with plenty of outdoor activities. Start with a leisurely stroll in the Walkway Over the Hudson State Historic Park to take in more of the autumnal views. Then, hop over to the Franklin D. Roosevelt National Historic Site and Locust Grove Estate. At home, you’ll find a fully stocked kitchen, two wood-burning fireplaces and a patio for lounging around on lingeringly warm afternoons. Pets are welcomed for an additional fee.
19. Treehouse (Middle Grove, NY)
Face it, the best thing about autumn is the changing leaves (and apple cider doughnuts). What better way to bask in the season than with a little fall vacation in the treetops? Just nine miles outside Saratoga Springs is this canopy treehouse in the foothills of the Adirondacks. To access it, you’ll need to climb the winding staircase, which leads to a sleeping area and covered porch. There’s also an outdoor kitchen and grill, with a fire pit located just over the footbridge by the stream. For all you bookworms, this feels like it’s straight out of Bridge to Terabithia.
20. Bellfire Tipi (Roxbury, NY)
In the fall, so many beautiful constellations come out: Orion, Andromeda, Cassiopeia, Canis Major…just for starters. Roxbury is a perfect place to go stargazing, surrounded by miles on miles of forest. The Tipi features custom furniture, wool blankets and cedar floors, with a kitchenette, fire pit, grill and hammock. Additionally, the property borders state land, so you can explore the vast wilderness (and take in some of the pretty fall foliage).
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