Spitfire Lake, Adirondacks
If you missed out on summer camp, make up for it at Camp Cobblestone, a twenty-acre estate on the banks of Spitfire Lake, where blue-blooded families have owned compounds for decades. The price is high for the Adirondacks, but it’s a unique spot, since other “Great Camps” (a designation applied to historic properties of this type) aren’t rented. Accessible only by boat, the camp is totally private, with eleven buildings including a turret-shaped boathouse and stone cottages that serve as sleeping quarters. A caretaker visits daily to keep the firewood stocked, and if you like to hike or bike, there’s a mountain trail.
Folkstone Road, East Hampton
The absolute rock-bottom price for a season in East Hampton. It doesn’t get more basic than this: a modest cottage deep in the working-class hamlet of Springs, where the taxes are the highest and the schools the most crowded. There are two small bedrooms, one serviceable bathroom, and a living room with a fireplace. Keep in mind: There’s a fifteen-minute winding drive along Three Mile Harbor Road to buy a carton of milk at Waldbaums. The best asset? Quiet Folkstone Road, which slopes toward Three Mile Harbor; at dusk, amble down to the water, and watch some of the prettiest sunsets in the Hamptons.
Rhinebeck, Dutchess County
Typically priced for the area, this turn-of-the-century converted barn is tailor-made for a large family. Located on five pastoral acres in the heart of rural Dutchess County, it has two master-bedroom suites (one with its own sitting room), another bedroom, and a den, sunroom, and patio. The grounds alone will keep the kids occupied for hours—catch frogs at the pond, explore the woods, walk the private trails, or play on the slide and swing set that take center stage on the enormous back lawn. Midtown Manhattan is a twenty-minute drive to the Amtrak or Metro-North stations plus a 90-minute train ride.
Saltaire, Fire Island
Writerly types in need of inspiration can try working at the desk of forbiddingly experimental novelist William Gaddis, who used to stay at this four-bedroom, two-bathroom renovated house. It’s an average price for Saltaire, one of Fire Island’s more exclusive towns—group rentals are forbidden, and it’s a favorite of celebs like Uma Thurman and Stanley Tucci—and slightly more than you’d pay in Ocean Beach, whose honky-tonk feel is just a water taxi away. Its pristine condition and location just a block from the beach make this a popular listing; pay $500 to join the yacht club and you can sail to your heart’s content.