Gentleman’s Farm

Stuyvesant, New York

The Details

Travel time: 2 hours.

Size: Sleeps 8.

Dates: All summer.

Price: $25,000 for Memorial Day to Labor Day.

Broker: David King, Gary DiMauro Real Estate.

Experience farm life without getting your hands dirty in this circa-1885 four-bedroom converted barn with exposed beams, wide-board floors, and a chef-friendly kitchen, complete with a restaurant-caliber Bertazzoni stove. The house sits adjacent to a 2,400-square-foot painting studio designed to make the most of the northern light. Next door is a silo, no longer operational but which serves as a reminder of the property’s past. The estate has fourteen acres of open fields that require no tilling—walk them or bike them, or sit on the deck and just take in the endless vistas. If you’re feeling inspired, the Spotty Dog Books & Ale (440 Warren St.; 518-671-6006), twelve miles away in Hudson, sells art supplies. Motivated cooks, meanwhile, can shop for ingredients on Saturdays at the Kinderhook Farmer’s Market (Village Green, Kinderhook).

Bespoke Cabin

Mileses, New York

The Details

Travel time: 2.5 hours.

Size: Sleeps 2.

Dates: June, and most of July and August.

Price: $250 a night (two-night minimum).

Source: airbnb.com/rooms/523841.

You’ll feel like you’re in a vintage L.L.Bean catalogue (or the Freemans dressing room) in this well-appointed one-room cabin. There’s no Wi-Fi and spotty cell-phone reception, but the house is kitted out with Hudson Bay blankets, a decadent Japanese soaking tub, and a framed copy of the Sportsman’s Code. It’s rugged and romantic—two couples have gotten engaged there in the past year. Photographer Matt Hranek had the place built on 130 acres of trails, ponds, and meadows with a classic hunting cabin in mind. The house comes with a Weber grill but no kitchen, so you’ll want to keep groceries to a minimum—there’s an old Coleman cooler for perishables and a French press—or head to nearby Callicoon, where you’ll find Peppino’s Family Pizzeria (27 Main St.; 866-955-9510) and Callicoon Wine Merchant (25 Lower Main St.; 845-887-3016).

Private Island

Clayton, New York

The Details

Travel time: 5.5 hours.

Size: Sleeps 18.

Dates: Most of June and July.

Price: $3,950–$5,950 per week or $14,500–$17,900 per month.

Source: homeaway.com/vacation-rental/p107219.

It’ll just be you, a gaggle of Canada geese, and up to seventeen of your friends on Watch Island, a 1.1-acre spit of land in the St. Lawrence River, 60 miles north of Syracuse. Get there via a ten-minute water-taxi ride (Clayton Island Tours; 315-686-4820) that departs from the Clayton Village Docks, or rent your own vessel from Chalk’s Marina (from $100 a week; 18221 Reed Point Rd., Fisher’s Landing; 315-686-4125). The ten-bedroom 1895 Victorian is the former summer home of financier and railroad heir Walter Jerome Green. The current owner, Marilyn Colangelo, bought the place in 1997, spent years restoring it, and has stocked it with anything you could possibly need, including books, movies, beach chairs, bikes, canoes, and paddleboats. For a night on the town, the Clayton Opera House (405 Riverside Dr.; 315-686-2200) is fifteen minutes away by boat.

Lakeside Hideaway

South Kent, Connecticut

The Details

Travel time: 1.5 hours.

Size: Sleeps 4.

Dates: July through August.

Price: $18,750 for July 15 to Labor Day.

Broker: Peter Klemm, Klemm Real Estate.

Lakeside camps used to rule this part of bucolic, woodsy Connecticut; this two-bedroom was part of one more than 30 years ago, but the owners refashioned it for the 21st century. (Knotted pine walls and a Shaker-style four-poster bed are complemented with stainless-steel kitchen appliances and décor hand-picked by interior designer Alexandra Champalimaud.) The 85-acre, spring-fed lake, South Spectacle, is one of the cleanest in the state; only 30 homes surround it. The house comes with a canoe and access to private tennis courts; while tempting, try not to stay put the whole time. The restaurants in the area rival those in the city. Joel Viehland’s Community Table (223 Litchfield Tpk., Washington; 860-868-9354), whose locally sourced menu changes weekly, is a gastronaut destination, as is the longtime fixture West Street Grill (43 West St., Litchfield; 860-567-3885).

Working Lighthouse

Newport, Rhode Island

The Details

Travel time: 3 hours.

Size: Sleeps 6.

Dates: July 14–21, July 21–28, August 18–25.

Price: $2,100 a week.

Source: roseislandlighthouse.org.

Few can say they spent their summer vacation helping skiffs and sloops navigate their way into Narragansett Bay. Bragging rights are yours if you sign up to be a keeper at the Rose Island Lighthouse, a mile off the coast of Newport. Stock up on provisions at the Stop & Shop (250 Bellevue Ave.; 401-848-7200) before meeting lighthouse director David McCurdy, who’ll ferry you over and lead you through a brief orientation. The daily chores, which include checking the batteries that drive the beacon, take just twenty minutes, leaving you plenty of time to swim, sun, and explore the eighteen-acre island with the rest of the tourists. The modest keeper’s quarters are located on the second floor of the lighthouse. Ask the staff for a lobster pot, which will come in handy when you catch one with the trap at the end of the dock (McCurdy or his crew can show you the ropes). Kids must be at least 5 to stay over.

Hamptons Mansion

Southampton, New York

The Details

Travel time: 1.5 hours.

Size: Sleeps 8.

Dates: All summer.

Price: $350,000 for July through Labor Day.

Broker: Gale Penny Conetta, Saunders.

Relive P. Diddy’s White Parties of yesteryear in this 6,000-square-foot, four-bedroom behemoth. You’ll be on Little Peconic Bay, not the ocean, but no matter—the house has loads of swagger. Own a yacht? Perfect: Skip the traffic and arrive by boat. (You can drop anchor next to the house, but you’ll need a dinghy to get ashore, as there is no dock.) The amenities here are plenty: 500-thread-count sheets, a wine fridge stocked with Dom, a private beach, and access to tennis courts that you share with a few neighbors. Double-height windows in the living room frame dramatic views of the East End sky. Spend your days splashing in the bay-abutting, 40-foot-long swimming pool or lounging in the covered cabana. A private chef can be arranged upon request, but Southampton’s toniest eateries—like the Plaza Café (61 Hill St.; 631-283-9323) and Sant Ambroeus (30 Main St.; 631-283-1233)—are minutes away.

Woodland Teepee

Lyman, New Hampshire

The Details

Travel time: 5 hours.

Size: Sleeps 6.

Dates: A few weeks in June; most of July and August.

Price: $65 a night (two-night minimum) or $390 a week.

Source: hikenewengland.com/tipi.

Have the forest to yourself in this 24-foot-tall teepee nestled within a private patch of woods near the base of the White Mountains. Firewood and a cooking grate are provided, as are several long-handled retractable forks for roasting marshmallows in the firepit. But pretty much everything else, including sleeping bags, is BYO. There’s no electricity, so bring a flashlight; you’ll be glad you have one when you start hearing owls hooting and coyotes howling. Come daytime, you’ll have the run of the 31 acres owned by the landlord. Those seeking a proper trek can hike the four miles of trails in the nearby preserve. Relax by the pond, located on the property, and watch the beavers perform what feels like a private show as they glide through the water. Note: There’s no bathroom or outhouse—this is nature as nature intended.

Amish Immersion

Intercourse, Pennsylvania

The Details

Travel time: 2.5 hours.

Size: Sleeps 11.

Dates: Three weeks in June, July 1–4 and 6–13, August 3–7, August 24–September 17.

Price: $225 a night or $1,200 a week.

Source: http://www.vrbo.com/348004.

Get back to basics with the Stoltzfuses, an Amish family that rents out its three-bedroom guesthouse by the day or week. There’s no TV or Wi-Fi, but there are foosball and Ping-Pong tables, plus Amish quilts blanketing all five beds. And though there is electricity (as well as A/C in the second-floor rooms), gas lanterns brighten the living and dining areas. The 70-acre property is a working farm, and you’re welcome to take part in daily chores like gathering eggs from the henhouse, feeding the pigs, or milking the cows—your hosts will show you how. Explore the village center, too, just a ten-minute drive away. It’s a hive of Amish culture, with the Amish Experience Theater (3121 Old Philadelphia Pk., Bird-in-Hand; 717-768-8400), and handcrafted quilts for sale at the Old Country Store (3510 Old Philadelphia Pk.; 800-828-8218).

Zen Retreat

Tillson, New York

The Details

Travel time: 2 hours.

Size: Sleeps 6.

Dates: Most of June and July.

Price: $300 a night (two-night min.) or $1,800 a week.

Source: airbnb.com/rooms/865653

Staying in this three-bedroom Hudson Valley home is about as close to the South Pacific as one gets in the tri-state area. Developer Ari Meisel had a friend reconstruct a Balinese estate on eight pastoral acres by importing a dense ironwood called ulin, piece by piece, from Bali. With it, he built three pavilions connected by covered walkways, with intricate carvings decorating the beams and columns. Each pavilion houses its own bedroom and has hardwood floors, terra-cotta tiles, and nearly floor-to-ceiling glass windows. There’s a separate cottage for overflow guests, and the spring-fed swimming pond out front is great for sweltering days. In nearby Rosendale, the Alternative Baker (407 Main St.; 845-658-3355) is known for its vegan, organic, and gluten-free indulgences. Those who can’t bear to leave should note that the house is on the market for $450,000.

Victorian Dollhouse

West Cornwall, Connecticut

The Details

Travel time: 2 hours.

Size: Sleeps 4.

Dates: Every other week from June through August.

Price: $215 a night.

Source: airbnb.com/rooms/543267.

Even the drive to this three-story 1870s Litchfield County Victorian is picture perfect: Pass through a covered bridge and you’ll spot it peeking through the leaves, perched on an oak-dotted hillside. The two-bedroom, one-bath house has undergone a top-to-bottom interior restoration and a systems overhaul, which means you can bask in period charm (bay windows, a claw-foot tub, exposed-beam ceilings) without forgoing the ease of modern conveniences (reliable plumbing and electricity). The décor is a shabby-chic mix of plush velvet chairs, Shaker furniture, perfectly weathered Oriental rugs, and knickknacks from local haunts like Michael Trapp’s antique shop (7 River Rd.; 860-672-6098), just up the road. Fill your days with walks to the nearby stream, afternoon dips in Cream Hill Lake, and kayaking excursions on the Housatonic River.