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