20 Vacation Rentals Perfect for a Fall Getaway (and Yes, You’re Gonna Want to Book ASAP)

If the back-to-school commercials and the Halloween window displays (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 beach, 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.

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Hudson Valley

The Hudson Valley is a popular destination year-round, of course, but we think it’s best enjoyed in the fall, when the foliage is bright and the apples need picking. And even if outdoorsy stuff isn’t your speed, with all the charming towns that dot the river, there’s no shortage of restaurants to try and local shops to browse. 

1915 Hudson Home

Usually we’re all about doing it for the memories, but in this case we’ll admit we’re doing it for the ’Gram. (And the proximity to adorable downtown Hudson.)


Rustic-Chic Barn

Nothing says “cozy fall getaway” like a rustic converted barn and an outdoor bonfire.


Tivoli Cottage

There’s a claw-foot bathtub next to the bed, so no one’s going to blame you if you don’t leave the bedroom all weekend.



The Catskill Mountains are a mecca for outdoor enthusiasts, with all sorts of trails to hike and lakes to swim. Enjoy that fresh alpine air from one of these stylish getaways.

Hunter A-Frame

This place is perma-booked all summer, and we expect the same in the winter (it’s on the ski slope), so now’s your best chance to enjoy this absurdly Instagrammable home.

Red Cottage

Modernist Cabin

This 1950s treasure sits along the Stony Clove Creek and boasts gorgeous mountain views and access to a private forest (!).

Red Cottage

Hillside Lodge

Backgammon, anyone? This log cabin is perfect for a small group of friends looking for a chill getaway of hiking and hot-tubbing.


Mountaintop Perch

Indian summer calls for lounging in hammocks and taking outdoor showers. And if it’s chilly, just curl up by the wood-burning stove.


Out East

Perhaps you missed the boat on booking a summer house out east this year. (Pro tip: Get on that in February). The good news is that you book during the fall, you’ll avoid the crazy summer price surges.

Sag Harbor Designer Retreat

Double-height ceilings and loads of natural light can be disorienting to us New Yorkers, but we’ll persevere if it means we can stay in this gorgeous contemporary home that’s walking distance to town.


Sagaponack Oasis

We hear fall Hamptons shares are all the rage (if you’re like us and don’t want to do any raging at all). Round up 11 friends for a weekend of lounging in the sunroom and exploring the nearby towns.


East Hampton Cottage

Located across the street from Round Swamp Farm (home to some of the best pies in the Hamptons), this cozy retreat features a sprawling lawn, an outdoor shower and a barbecue for those unseasonably warm September days.


Wine Country Estate

Is that Tuscany? Nope, it’s the equally enchanting North Fork. And the saltwater pool is a prime spot to watch the sunset.



Connecticut has a ton of variety for a small state, which means there’s a rental property for every taste. So whether you’re looking for a beach escape, a wilderness retreat or a literal castle, you’ll find it only a short train ride from New York. 

1930s Stone House

If that trip to the English countryside isn’t in the cards, may we suggest this Granby stone home instead? 


Mid-Century Modern Abode

Put on your pencil skirt and pour yourself a stiff drink at this Zen retreat on the property once owned by sculptor Gutzon Borglum, aka the dude who designed Mount Rushmore.


Beachfront Escape

Got a flexible job situation? Post up for an entire month and work remotely from this perfectly appointed 1930s cottage. That deck, though…


New Jersey

The Garden State is full of surprises, and that includes some truly enchanting rentals that make for the perfect home away from home. 

Historic Cape May Guesthouse

The charming town of Cape May is a history buff’s heaven, and this Victorian home is no exception. It’s now divided into four spacious suites, each complete with its own kitchen.


Jersey Shore Victorian

The stained-glass windows and hydrangeas are reason enough to book this property, but the proximity to the beach and Ocean Grove don’t hurt.


Totally Unique

As the old adage goes, it’s not the destination, it’s the journey… around your totally wacky vacation rental. So if you don’t care where you escape to and are more interested in having a unique experience, check out one of these coveted rentals. 

Adirondack Tree House

Your inner 8-year-old needs to stay in this adorable treehouse that sleeps three. Just down the stairs, you’ll find an outdoor kitchen, a fire pit and a full bathroom. (BYO tin-can telephone.)


Tepee Hideaway

Skip the frustration of trying to assemble a tent and relax in this luxe tepee instead. (Yep, that’s a fully functional fire pit.) Bonus: It’s located in one of the best areas for stargazing in New York state.


Tiny Home on a Farm

Look, the irony of trading our shoebox of an apartment for a tiny house is not lost on us. But its location on a 12-acre farm (complete with goats and rabbits) in the middle of the forest makes for a nice change of scenery.


Storybook Castle

We may have to wait until 2019 for Game of Thrones to return, but at least we can live like a queen at this New England castle, built in 1917. (Don’t worry, the interior is fully modernized.)

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