The Wildest Houses You Can Rent in Upstate New York

We’ve all been itching to travel, and bust our bums out into the wilderness for some Sunny D, skinny dipping, and fireside chatter. But we’re also kind of lazy, and want to plan our galavanting as close to home as possible. Plus, it’s a whole lot easier to wrangle the crew for a weekend jaunt in a nearby town than it is to scoot everyone to Positano [sigh]. 

But also, who needs Italy? (We needs; we just can’t have it on our current budget.) Scope hard enough, and you can find Mediterranean-style villas in upstate New York that feel worthy of Sophia Loren; do a bit of digging, and you can find bonkers vacation rentals on Airbnb and Plum Guide (the latter of which is a treasure trove of highly ~*aesthetic*~ homes) for you and a dozen of your friends to break bread, pass the poppers, and create unforgettable memories in a setting that looks like the set of an A24 film. Remember: People are talented, but the people upstate of New Yakh City have a special streak of poetry in their hosting, and will invite you into converted boats, school houses, barns, and more. 

Sometimes the best wood-shingled hippie pads for you and your burgeoning cult are right under your nose. Here are the ones on our bucket list, whether upstate NY is an hour (or five) away from your abode. 

The purple mood lighting and poolside floor poufs say, “totally, man.” This Woodstock house comes with its own spa, porch, fully equipped kitchen, and a king-sized bed with a 1910 fireplace. You know, for the drama. 

Private SPA; sleeps up to 8, $600/night at Airbnb

Guess we can just stop the article here, because where can you go from a bespoke dome home in New Paltz that looks like it was built by aliens in the 1970s? At the heart of over 28 acres of your own private forest, this home comes complete with a tub, baby grand piano (and powerful outdoor speakers), and some bitchin’ Wi-Fi. There’s even a towel warmer. (We may never leave.) 

Unique Dome Home on 28 Acres with Hot Tub & Piano; sleeps up to 6, $598/night at Airbnb

Does your crew run deep? This sprawling home in Blooming Grove, New York can accommodate up to 18 guests, and sits on the edge of a forest. There’s a huge cast-iron fireplace, and the main bedroom’s ensuite is described as having a “Japanese zen feel to the wood-lined shower and onsen-style jetted tub.”

Woodcutter’s Rest; sleeps up to 18, $525/night at Plum Guide

Che spettacolo! Who needs Italy when you can rent out this villa worthy of Michelangelo in Catskill with mountain views? You and up to 14 friends can sprawl out over the five-acre property with a pool, fire pit, and surrounding activities like tennis, boating, and other Lana Del Rey-core East Coast shenanigans.  

Mediterranean Villa with Pool; sleeps up to 14, $445/night at Airbnb

For those who want to feel like they’re in an A24 movie, we present this miniature A-frame cabin in Freehold, New York. It has an impressive five-star average rating and comes equipped with a fire pit and a hot tub for memorable, toasty nights.

Tiny Home A-Frame with Hot Tub & Creek; sleeps up to 3, $284/night at Airbnb

Calling all hot cottagecore people: This shingled abode in Woodstock, New York is dressed in the perfect amount of fairy lights, is equipped with Smeg appliances, and, most importantly, a hot tub. No wonder it has a coveted five-star averafe rating from reviewers.

Cozy and Eclectic Woodstock Getaway; sleeps up to 3, $232/ night at Vrbo

There are a lot of rental homes designed by famous architects out there, but this one was designed by the visionary Philip Johnson in the late 20th century. This home on the Hudson river stuns from the inside out, and the glass-filled interior lets in plenty of light and feels like a private wing at the Getty Museum, while the panoramic views inspire us to pop the question. (The question being, “Which natty wine are we opening tonight?”)

A New Perspective; sleeps up to 8, $1,611/night at Plum Guide

There are some Airbnbs that just make us feel richer, if only for a few nights. This [pulls back velvet curtains] is one of them; located in Amenia, this fancy farm has Downton Abbey-worthy interiors and all the dogs, horses, and goats you could hope for. There’s even a therapy pig named Shackelton, if your heart didn’t melt enough already. 

Luxury Horse Farm by the Room; sleeps up to 6, $300/night at Airbnb

The hosts of this "Adirondack Tree House Retreat" on Airbnb describe it as "one of the most sought after places for couples to reconnect with nature." That's right—the real mile-high club shouldn't be the cramped, germ-splattered bathroom on a red-eye flight to O'Hare; nope, it should be a genuinely romantic setting with a bird's eye view, like this mega-cute elevated cabin with a winding staircase and outdoor kitchen. 

Adirondack Tree House Retreat; sleeps up to 3, $275/night at Airbnb

A close-enough facsimile for Bali is only a drive away from your Brooklyn pad, and with all the picturesque, waterfront vibes you've been craving. This house has it all: a sprawling 7.5 acres of wooded surroundings, including grasslands and a private, spring-fed pond; four individual "pods" connected by enclosed outdoor walkways, for peaceful privacy; a chef's kitchen, a bathtub next to a fireplace, and even a hot tub. Plus, it was even made with imported materials from Indonesia. "Working" from "home"? There's also super-fast Wi-fi and Apple TV. "I'm still not sure [whether] it is the memories of vacations in Bali or Thailand that get waken up while I'm here or the serene location or maybe there are some magnetic fields deep underground," the hosts write, "but I tell you, I sleep better here than anywhere else." 

Hudson Valley Bali House Retreat; sleeps up to 8, $529/night at Airbnb

Now this is the kind of elevated camping (OK, “glamping”) we’re interested in. It’s part sailboat, part farmyard outpost, and you’ll be nestled in between “a beautiful stream and a row of trees bordering the main horse corral” in the town of Accord, hosted by a couple of self-described “hippies at heart.”

The Hangout w/ Yoga Deck on Horse Farm; sleeps up to 16, $106/night at Airbnb

Just a four minute walk from the Hudson waterfront you’ll find this 1970s-style home, whose massive windows will bathe you in light and the surrounding natural landscape. There’s ample patio space for barbeques, and a hot tub for relaxing after dinner with some bubbly jets and a glass of pinot grigio.

House in Highland; sleeps up to 6, $455/night at Vrbo

Just imagine roasting a duck here with your closest friends, each of you wrapped in a cashmere throw with a highball in-hand, staring out one of the gazillion glass windows of your modern Woodstock estate. This home is complete with a heated saltwater pool and cedar tub, and was the winner of the 2009 American Institute of Architects Design Award (which we can’t wait to tell Mother on the phone, to prove… something?).

Modern Woodstock House in the Trees; sleeps up to 8, $850/night at Airbnb

Sold. And while we’re soaking, you can explore “the array of activities the spot has [to] offer, with a barbecue, fire pit, ping pong and foosball tables, kayaks, and a deck to jump straight into the freshwater lake.” 

Pine’s Reach; sleeps up to 10, $1,165/night at Plum Guide

Once upon a time, you were a teenager heading to Coachella to wrap yourself in glow sticks and the sweet vocals of Prince. Now you and up to 16 of your kind-of-close (but really fun) friends can recreate the magic in this Woodridge geo dome.

Outlier Inn Geo Dome 1 on Farm Upstate Catskills; sleeps up to 16, $379/night at Airbnb

You’ll feel like you’re sleeping in the trees in this secluded, minimalist estate in the Catskills (but in a classy way, not a woodpecker way), which is complete with its own pool table, art books, and should quite frankly be the setting of someone’s aesthetic, Danish horror movie. No bad angels on this baby, just vibes. 

Kodama; sleeps up to 6, $2,193/night at Plum Guide

Definitely the kind of place where our lucid, Nancy Meyers dreams take flight. This 1820s manor sits on the edge of a Catskills swimming creek, with a “waterfall cascading over an ancient dam of hand-laid stone” and a giant outdoor dining table for you and your buds to host a farm-style dinner into the wee hours of the night. 

Floating Farmhouse; sleeps up to 10, $2,032/night at Plum Guide

This converted barn in Uster County, New York comes not only with a hot tub but its very own music studio—just in case you decide it’s time to finally drop the track that you and the nine other people (the house sleeps up to ten) invited to the weekend getaway have been perfecting over the many years of your friendship.

New Barn Home; sleeps up to 10, $690/night at Vrbo

The Berkshires has long been a pull for artists looking to escape the city and seek inspiration in Mama Nature, and this converted 1866 schoolhouse is the perfect place for you to finish your memoirs (or start them). It sits right by Wahconah Falls State Park, and has a gorgeous 1920s bar for unwinding with a martini after your ~pensive~ strolls. 

River Song; sleeps up to 10, $499/night at Plum Guide

What a place to have a stylish midlife crisis. We can just picture ourselves sipping wine from the crow’s nest, overlooking the rest of the North Fork before heading down to the private beach. Big Little Lies, but put it on the East Coast. 

The Old Life-Saving Station; sleeps up to 14, $1,469/night at Plum Guide

This pop art-filled home is in the town of Fleischmanns, surrounded by nature and perched over a stream. There’s a “humongous kitchen [that] is perfect for preparing a convivial feast with friends,” says the host, and your proximity to both the Belleayre Ski Resort and bus stop makes it an easy place for friends to come and go from the 3,000-square-foot playground.

Catskills Pop Art House; sleeps up to 10, $375/night at Airbnb

This is where you go to seek all your Japandi design inspiration. Located in the Catskills, this minimalist home is like the chicest oversized rectangle we could ever hope to break bread in; the beauty’s in the details of the marble bathrooms, lava stone and Italian Porcelanosa tiles, and the proximity to nature (there’s also a campfire on-site). 

The Edge; sleeps up to 6, $1,466/night at Plum Guide

The king of turning on, tuning in, and dropping out may have done so over at his mansion in Millbrook, New York, but this white Woodstock estate is giving us the same acid-tab nostalgia. It’s spread out over 26 acres of land, and is just five miles from downtown Woodstock. There’s a cedar hot tub, a large wraparound porch, and all kinds of architectural details that you just don’t find anymore. 

Magical Woodstock Getaway; sleeps up to 10, $400/night at Airbnb 

Meanwhile, in Rondout Valley, this home invites you and your buds to live out your Captain Fantastic fantasies over 75 acres of woodland complete with a pool, campfire, stables, and (for a little extra) whimsical glamping tents.

Hawk & Falcon; sleeps up to 10, $2,522 at Plum Guide

God, we love this Hallmark movie. “Summer at the Barn is like summer camp, but with comfortable beds and AC,” writes the host of this home in Tivoli. They encourage you to “grill epic meals, go on hikes, relax [in] the hammock,” and take a dip in the stream before warming up by the fire pit. 

The Barn in Tivoli; sleeps up to 5, $495/night at Airbnb

OK, so it's not exactly a "house." But the Roxbury Motel is a cult fave for lovers of kitsch, and it is definitely a wild place to lay your noggin. Essentially the East Coast version of the Madonna Inn, the Roxbury is comprised of dozens of maximalist rooms and suites, from the futuristic, Star Trek-themed "Final Frontier," complete with intergalactic views, to the luxurious "Digs," a standalone cottage with "hidden treasures and maps, secret passageways, fulfilled prophecies, Gods, libraries, idols, reptile skins, surround-sound television, ancient curses, leather, hieroglyphics, bull whips, solid gold, fire features, Mayans, Egyptians, Mesopotamians, Micronesians, Indians, Romans, Spartans, Arabians, Aztecs, Siamese, Trojans, Crusaders, kings, queens, torches, babbling brooks, relics, and the ability to take a shower next to saltwater fish that are protecting Cleopatra’s long lost underwater tomb." [Inhales.]

Yes, this place is nuts, and we're obsessed. 

The Roxbury Motel, starting at $165/night at TripAdvisor

Stuck on the West Coast? Let’s head over to Joshua Tree. 

The Rec Room staff independently selected all of the stuff featured in this story. Want more reviews, recommendations, and red-hot deals? Sign up for our newsletter.