Orient, not Montauk
If you miss the days when Montauk was still a sleepy, scrappy hamlet—no valet parking, no $70 pitchers—head to Orient, the North Fork’s easternmost point, known for its miles-long nature trails and untouched beaches. According to Corcoran, the village has a parade of nineteenth-century clapboard Cape Cod–style cottages, many costing a fraction of Montauk’s askings. A pool-and-tennis-court-equipped six-bedroom in Orient, for example, is $160,000 a season; in Montauk, you’re looking at $360,000 for a five-bedroom oceanfront.
South County, not Cape Cod
You’ll get a classic New England beach vacation—swimming, antiquing, lighthouse-climbing—in either of these destinations, but opting for Rhode Island’s southern stretch of beach towns will cut your travel time in half. The rental market is robust, too, with plenty of reasonable options, says Cecile Cohen of Randall Realtors. A two-bedroom saltbox Colonial runs around $900 a week on the low end in Charlestown and Narragansett; other rentals fall between $1,200 and $2,500 a week and often include a beach pass.
Milford, not Cape May
Cape May gets all the love for its sweet Victorians, but historic Milford has plenty of storybook houses, too. Located on Pennsylvania’s Delaware River, it’s a prime destination for kayaking, canoeing, and swimming. (It’s also closer to New York—just 71 miles to Cape May’s 158.) There aren’t a ton of rentals in Milford—a dozen are advertised on vrbo.com, some for under $200 a night, others averaging $2,000 a week. But plenty more are available in the nearby lake communities, says broker Davis Chant.
Old Saybrook, not Westport
It’s about half the size of coastal Westport and an hour farther from Manhattan, but Connecticut’s Old Saybrook is worth the trek for budget-minded seafarers: You can still sail on the Long Island Sound and canoe the Connecticut River, but these rentals are available by the week. Halstead Property’s Karen Curtis says Westport housing is currently running between $3,100 and $22,000 a month; in Old Saybrook, comparable homes start at around $1,000 a week. And Saybrook is just as charming, thanks to historic homes on verdant streets, idyllic beaches, and top-notch programming at the Katharine Hepburn Cultural Arts Center.
Northern Dutchess County, not the Berkshires
There’s no arguing the cultural heft of Tanglewood and Williamstown. But Northern Dutchess County serves culture hounds just as well during its SummerScape Festival (July 5 through August 18) at Bard College. The village of Red Hook is popular for weekenders, and if you don’t need the entire summer, an August rental is easier to find. Also consider woodsy Milan to the east or head north to the hamlets of Germantown, Livingston, and Elizaville, where demand is lower. Patricia Hinkein Realty has a handful of seasonal rentals available, starting at $2,750 a month for a two-bedroom cottage.
New Paltz, not Woodstock
Woodstock’s brother-from-another-hippie-mother, New Paltz, has its fair share of organic cafés and shops hawking dream catchers. But it’s closer to the city by 45 minutes and is anchored by a thriving college town, with access to SUNY New Paltz’s offerings, including the well-regarded PianoSummer Music Festival (July 6 through 26). For hiking and rock-climbing enthusiasts, the Shawangunk Mountains are six miles away. Airbnb.com has dozens of rentals available here, from a $225-a-night two-bedroom in town to a $700-a-night 4,000-square-foot 275-year-old stone mansion.