$5,000 and Under
Channel your inner hippie without roughing it at this ultramodern, 1,000-square-foot cabin in the woods. Just a two-hour drive from the city, the rental is a favorite among young couples from the East Village and Park Slope who appreciate the Asian-slate floors, marble bath, and other designer-y touches (pay any less around here and you’ll get that ski-cabin feel). After a day of hiking, rock climbing, or swimming in the natural, spring-fed pools nearby, renters especially like a dip in the claw-foot bathtub, which sits right in the middle of the living room, with views of the surrounding forest.
Kismet, Fire Island
This seven-bedroom rental in the so-called Williamsburg of Fire Island may redeem the much-maligned share house. Chance, as it’s known, seems slightly more expensive than a half-share in the Hamptons, until you realize you get four more weeks for your money here. It’s usually populated by hipsters who want to sink their teeth into “trash-talking” Scrabble games in peace: Be prepared to bunk with housemates from Dumbo, Carroll Gardens, and—yes—Williamsburg. (There’s a bonus: Many of them are foodies.) And, of course, there’s the beach, still unspoiled and just 50 feet away.
Mohegan Bluffs, Block Island
This five-bedroom turn-of-the-century cottage edges into the upper range for Block Island, but it’s cheaper than comparable rentals in Water Mill or Southampton. Perfect for kayaking and surfing, it’s perched on the edge of the dramatic Mohegan Bluffs, which rise 200 feet above the water—a private staircase leads you to the sandy beach below. When you don’t feel like dipping in the water, lounging on the massive porch, or enjoying the views of Montauk, take advantage of the miles of trails maintained by the Nature Conservancy, or the island’s five named beaches, 365 freshwater ponds, and numerous little coves.
Two and a Half Weeks
Manhattan families used to making do with cramped spaces will find this pricey but pretty four-bedroom, four-and-a-half-bath colonial truly decadent. It’s furnished floor-to-ceiling in antiques (and reproductions) and kid-friendly gear, has a glassed-in sleeping porch that’s great for gazing at the star-speckled nighttime sky, and resides on 29 rambling acres with views of Bear Mountain, the state’s highest point. There’s a tree house and a swing set to sweeten the deal, and if that’s not enough, the town is known for its two freshwater lakes, great day camps, and cute events like the remote-controlled New England Grand Prix.