Country clubs be damned: This getaway in the historic Ellsworth neighborhood of this exclusive town has everything you need for a month of R and R, starting with a 56-foot-long heated pool and a tennis court. It’s in the mid-to-high range for the area, appropriately so: There’s room to roam—two manicured acres—and entertain—four bedrooms in the main house and a guest apartment to handle any overflow. If you must seek entertainment elsewhere, the Berkshires are just 20 minutes away. Another perk (maybe): You’ll be within six degrees of Kevin Bacon, who summers here.
Great Barrington, Berkshires
It’s easy to waste weeks doing nothing but relaxing amid the lazy meadows, postcard mountain views, and sleepy lakes of the Berkshires. The artsy village where this circa-1850 post-and-beam barn is located should entice anyone onto their feet, though—it’s close to festivals and arts institutions like Tanglewood, Jacob’s Pillow, and Shakespeare & Company. The original plank floors are still in place, but it’s hardly rustic; there’s central air and a high-speed Internet connection. Mid-to-high range for the area, this is comparable to the best houses on Cape Cod.
This four-bedroom house overlooking Nantucket Harbor is relatively affordable, given that prices on the island go as high as $180,000 a month. It has five bathrooms, a gourmet kitchen, and a gym, and, of course, you can watch the yachts shimmy into port. There are plenty of outdoor activities on the island, including biking, hiking, and windsurfing, but many of the celebs—like Tommy Hilfiger and Tim Russert—who swell its population from approximately 9,000 to 50,000 in summertime are content to do nothing but eat lobster and relax on the languorous beaches.
Cape May, Jersey Shore
The entire town of Cape May is landmarked, which may explain why it’s not marred by the beer-soaked, frat-party vibe typical of the Jersey Shore. Peppered with stately Victorians and quaint cottages, it’s decidedly kitschy, but in an appealing, apple-pie way. This seven-room mansion is typically priced, and Civil War buffs will enjoy bunking in a place once owned by Yankee hero Henry Sawyer, who built the legendary Chalfonte Hotel across the street in 1876. (The house isn’t completely traditional—it’s got A/C and DVD players.) White beaches are just three blocks away.