Woodstock, New York
What: Two-bedroom, one-bath apartment.
Price: $975 per week through June; $1,175 per week in July and August.
Contact: Jeff Cuiule (845-750-9484)
Get there: Two hours from Port Authority on Adirondack Trailways.
The bus drops you across the street from Above the Books, the upper floor of a century-old Victorian owned by Cuiule and his wife, Audrey Cusson (they run Mirabai Books downstairs; all renters get a 10 percent discount). It has a meditation room, and the walls are painted with organic aromatherapeutic oils (this is Woodstock, after all). Billy Denter, the friendly owner of Overlook Mountain Bikes, will rent you a basket-equipped bike. There are two markets nearby: the Sunflower (groceries, good deals on bulk bin foods) and the slightly pricier Sunfrost Farms (produce, plants, good sandwiches and juices at the lunch bar). Pack old sneakers to navigate the rocks into the Tannery Brook Road swimming hole. Athletic challenge: Ride up Rock City Road by the Buddhist temple, then hike to the ruins of Overlook Mountain House. There’s summer-stock Shakespeare at the Woodstock Playhouse, and Maverick’s famous outdoor jazz and classical-music series. Make the Woodstock Lodge your drinks spot; it’s recently renovated, with an Italian-Cuban menu and a roomy bar.
What: Three-bedroom, two-bath with sleeping loft.
Price: $3,000 per week from May to September.
Contact: Pamela Wall, Cool Cribs Real Estate (203-227-9873)
Get there: One hour on Metro-North.
Wall, a former New Yorker, put a lot of style into the renovation of her bungalow expressly because she wanted to appeal to city dwellers who are burning out on the Hamptons and looking at Westport instead. It’s only a five-minute, $5 cab ride from the station, but the house, on a cul-de-sac in the middle of Saugatuck Shores, a peninsula that juts into the Long Island Sound, feels much farther away. Westport Bridge Market will deliver staples. Everything for a satisfying beach stay is within walking or biking distance (some area highlights, like the Westport Country Playhouse and Paul Newman’s organic restaurant Dressing Room, require a taxi ride). BYO bike or walk to go to the beach, the Longshore Sailing School (rent a canoe for $20 an hour), and Levitt Pavilion’s open-air concerts: for kids on Wednesdays, classical on Thursdays, jazz, blues, and big band on Sundays. Bring the kids to Compo Beach to watch the skateboarders and kite fliers gather and where they can work off energy at the playground.
Sag Harbor, Long Island
What: Three-bedroom, two-and-a-half-bath traditional with a garden.
Price: $14,000 for July.
Contact: Cynthia Barrett, Prudential Douglas Elliman (631-537-6069).
Get there: Two hours via Jitney or Long Island Railroad.
The jitney stops a block from this clapboard-clad three-bedroom built in 1800 (its interior was recently renovated), back when Sag Harbor was a thriving fishing village (if you take the LIRR, it’s a $10 cab fare from Bridgehampton station). Before you head over, stock up on beer, bread, and the basics at Schiavoni’s Market on Main Street, a longtime fixture that carries everything from organic pasta to gourmet coffee as well as homegrown products like Hamptons Honey. Road or mountain bikes are $45 a day at BikeHampton on Main. Post-unpacking, head to Haven’s Beach, a white-sand beach by the bay with a playground. (It’s five minutes on bike.) There’s plenty to do besides beachcombing: art films at the Sag Harbor Movie Theatre, local maritime history at the whaling museum, yacht-ogling at the marina, hiking the Long Pond Greenbelt trail. If it’s overcast, rummage through the stacks of Sag Harbor’s independent bookstores (BookHampton, Black Cat, and Canio’s), or taste cheeses at the widely adored Cavaniola’s Gourmet Cheese Shop.
Dunewood, Fire Island
What: Three-bedroom, one-bath cottage with an outdoor shower and deck.
Price: $13,000 for August.
Broker: Kitty King, Kitty King Real Estate (631-583-8927).
Get there: About an hour on the LIRR, five-minute shuttle to the ferry, 25-minute boat ride.
Small and intimate—there are just 99 houses—Dunewood is one of the sleepier towns on famously sleepy, carless Fire Island. The house, a sun-washed one-story, sits five lots from the ocean. Like most rentals, it’s equipped with pedal-brake bikes and the requisite red wagon for errands. You’ll need to walk to Fair Harbor (ten easy minutes by foot) for groceries. There’s a well-stocked general store (Eli’s breads, pomegranate juice), a good wineshop, a pizza stand, and the surprisingly upscale eatery Le Dock for nights when you’re tired of grilling. The long, wide ocean beach is the main attraction, although young children may prefer the calmer, lifeguarded bay side—which, since it’s Fire Island, is only a slightly longer walk. There’s a day camp in Saltaire, two towns over, that will teach kids swimming basics. For excitement, call a water taxi to honky-tonk Ocean Beach (souvenir stores, more restaurants, a cinema) or to the Pines, the island’s largest town and host to August’s Ascension, the gay-and-lesbian beach party that draws thousands.