The view down a beach in the Hamptons
The Hamptons are one of many places you can safely shake off your shelter-in-place blues this summer.
Bridget Shevlin
By Austa Somvichian-Clausen / May 27, 2020 1:14 pm

A true New Yorker’s love for the city is unconditional. Nothing unites its inhabitants more than a sense of collective struggle, whether that means passing a knowing glance to one another on a packed 9 a.m. Subway car or seeing a fellow Uber rider stuck in Midtown traffic on the way to spend $17 on a cocktail. But since the coronavirus pandemic hit, those invisible connections have grown even deeper.

With that being said, New Yorkers are also bonded by something else: the joy of leaving the city, if only for a fleeting summer weekend. But amid the current circumstances, are upcoming summer trips even going to be viable?

On May 15th, Governor Cuomo began Phase One of unpausing New York, starting with the five regions of the state that met all seven of his criteria: Mohawk Valley, North Country, Southern Tier, Finger Lakes, and Central New York. A few others are on the verge of meeting those criteria. 

According to Cuomo’s guidelines for reopening, each phase will be in effect for at least two weeks, and comes with a new round of reopenings for certain nonessential businesses. Phase Two includes businesses such as in-person retail and real estate; Three extends to restaurants and other food services; and the fourth phase will see the reopening of arts, entertainment, recreation and education. If each phase moves forward at the two-week mark, more than half of the regions in the state will be fully reopened by the end of June.

With all that in mind, can you ethically vacation this summer? Probably, but that trip won’t (and shouldn’t) look anything like your party-hopping Hamptons days of yesteryear. It will still be important to stay as isolated as possible to continue to flatten the curve.

If you are thinking about heading back to your favorite vacation town this year, try to avoid crowded streets and packed beaches. Opt instead to venture farther out of town, where you’ll probably snag a much grander property as well as the chance to reconnect with nature and close friends or family in a way that keeps you, and others, safe. And before you start your drive over, be sure to stock your car with supplies — from the cleaning gear you’ll definitely need to the bottles of wine you know you’ll want — in order to avoid disrupting another town’s supply chain. Finally, regardless of where you and your party choose to head this summer, make sure to read the fine print before booking, and expect cancellations.

With all that said, we’ve taken the liberty of compiling 11 rentals within driving distance of NYC that are appropriately isolated, still have late summer vacancies and specify flexible cancellation policies. Prices are based on the same dates in August for each property, and are subject to change.

1. A secluded lodge in the Catskills

Photo courtesy of Airbnb

Looking for a true escape? This stylish lodge in the Catskills sits on a private drive, bordered by 20 thousand acres of public land as well as ample trails for hiking and biking, streams, lakes and forest. Luxe amenities — like a brand new chef’s kitchen and hot tub by an outdoor fireplace — mean you’ll have plenty to do without even leaving the premises.

The specs: 4 bedrooms, 4 beds, 3 bath | $403/night

2. A renovated Hamptons barn in Sagaponack

Photo courtesy of Airbnb

This renovated Hampton’s Barn is walking distance to both Wolffer Vineyard and the water. The barn supposedly belongs to a famous artist, so those looking for a little inspiration might want to shack up here for a weekend. Located on the coziest street in Sagaponack, the house is only a quick bike ride away from the beach where surfboards and bikes are available to rent.

The specs: 1 bedroom, 1 bath | $400/night

3. A modern mansion with a hot tub and pond in Upstate NY

Photo courtesy of Airbnb

An hour’s drive from Manhattan will bring you to the Mission House Sanctuary. This private villa has all of the upgrades you could hope for, from a grand-scale wood burning fireplace to a master bedroom and bathroom that overlook your own private lily pond. Outdoorsy guests will love that it’s located less than a mile from the Appalachian Trail. 

The specs: 4 bedrooms, 5 beds, 4 baths | $400/night

4. A spacious private cottage at the Finger Lakes

Photo courtesy of Airbnb

The Finger Lakes region is one of the five that Cuomo deemed ready to begin phase one of reopening. There, you’ll find this lake cottage two miles from the village of Penn Yan. With spectacular views of the lake, a dock and hoist for a boat, and a fully equipped kitchen, this cottage is the perfect option for a relaxing nature getaway.

The specs: 3 bedrooms, 4 beds, 2.5 baths | $450/night

5. A romantic cabin on West Sand Lake

Photo courtesy of Airbnb

Located on a farm, the Lodge at June Farms is a “stunning, rustic, open-floor-plan retreat” that was featured on the season finale of Bravo’s Backyard Envy. The screened-in front porch looks down onto a picturesque horse pasture, and the vibes are made even more romantic by a rain shower with a French door that opens out to the forest. For adventure seekers, they have ATVs, golf carts, snowmobiles or Kawasaki Mules available to rent.

The specs: 1 bedroom, 1 bath | $275/night

6. A beautifully restored antique home in Martha’s Vineyard

Photo courtesy of Airbnb

This luxurious home is a fairly centrally located in downtown Edgartown, on a quiet block just a few minutes away from Main Street, Fuller Street Beach and Edgartown Harbor. Spend time soaking up the sun in the garden or open up the windowed doors in the sunken living area, which originally served as a large summer porch. 

The specs: 5 bedrooms, 7 beds, 5.5 baths | $2,200/night

7. A waterfront cottage with a private beach on Joshua Cove

Photo courtesy of Airbnb

Spend the evening watching the sunset from your own private beach with this modern cottage on the water. Although the house is just a short drive to New Haven and the Yale University campus, the property looks well-removed from the action, with plenty of space to roam and its lakeside location providing ample opportunities for kayaking, swimming and fishing.

The specs: 1 bedrooms, 3 beds, 1.5 baths | $400/night

8. A mid-century chalet in the Catskills

Photo courtesy of Airbnb

This stylish chalet with soaring ceiling and hand-picked furnishings has been ranked among Airbnbs in the Catskills. The listing boasts amazing WiFi service, so if you’re staying for an extended period of time you wouldn’t have to worry about your ability to work remotely. There’s plenty of relaxing to be done here too, though, with a stone fireplace inside and a clay tennis court outside. 

The specs: 3 bedrooms, 6 beds, 2 baths | $365/night

9. An A-frame cabin with a private beach near Fire Island

Photo courtesy of Airbnb

We’re already suckers for an A-frame, but plop it right next to a private beach and it’s a done deal. This one has awesome views of Great South Bay, whether from inside the house or from the deck as you grill. The listing emphasizes deep cleaning in between guests, and a contact-free check in process using a keypad lock. 

The specs: 3 bedrooms, 6 beds, 2 baths | $365/night

10. A modern-rustic guesthouse on 52 acres in Ghent

Photo courtesy of Airbnb

This newly renovated guest house in Upstate is situated on 52 acres of countryside, where you can hike private trails in the woods, cook and read a book by the pond. Inside the property enjoy cozy amenities like a wood-burning stove and a clawfoot bathtub.  

The specs: 1 bedroom, 1 bath | $180/night

11. A sleek house with ocean views and a private pool on Fire Island

Photo courtesy of Airbnb

This spacious home in Ocean Bay Park really has it all — from the flatscreen inside to the backyard patio with a private pool and beach chairs. After preparing a meal in the well-equipped kitchen, head up a set of spiral steps to a furnished terrace with ocean views. This listing is perfect for families too, as the home has a strict 30 year-old minimum age requirement that doesn’t apply to families with children.

The specs: 4 bedrooms, 5 beds, 4 baths | $1,276/night