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Chicago: Sawyer, Mich.
Travel time: 2 hrs.
Chicagoans have escaped to the eastern shores of Lake Michigan for ages. Yet few venture to the Sawyer area, which boasts three miles of shoreline backed by wildflower-strewn dunes and elm forests. Cottage at the Dunes is a three-bedroom jewel with a wood-burning stove, quaint cottage decor, and proximity to Warren Dunes State Park's 240-foot sand banks ($1,700 per week). Drive 20 minutes east and you're in Michigan wine country. Round Barn Winery produces several worthwhile whites and fruit brandy. Nearby Lemon Creek is known for its dry reds.
Dallas: Bend, Tex.
Travel time: 4 hrs.
The rough-and-tumble antidote to Dallas, Colorado Bend State Park has a deep canyon rimmed with limestone bluffs and a fertile floodplain of lush groves. Canoe downstream to Lake Buchanan, hike 60-foot Gorman Falls, or take a ranger-led caving trip. Stay at rustic Sulphur Springs Camp, which has a spring-fed swimming hole and five air-conditioned cabins with cliff views ($69 per night). Each has a barbeque pit, but the nearby Cooper's Old Time Pit Bar-B-Que (a Dubya favorite) is famed for mesquite-smoked brisket and pork ribs (Bush's pick).
Atlanta: Asheville, N.C.
Travel time: 3 hrs.
Nestled in the Blue Ridge Mountains, Asheville balances boho culture and Appalachian tradition—and it's less trafficked than antebellum Savannah, Ga. Rent Rainbow Ridge, a two-bedroom cabin with a hot tub and sunset views. It's 15 minutes from town but still woodsy and remote ($578 for three days). The Biltmore Estate, a museum and 8,000-acre park (day pass, $60), is a glimpse at the town's Gilded Age glory. At night, locals bring fiddles to Jack of The Woods for impromptu jam sessions; others hit The Orange Peel, ranked by Rolling Stone as one of the coolest live music venues in the U.S.
Seattle: San Juan Island, Wash.
Travel time: 2 hrs.
It's easy to find a place to paddle along the Puget Sound, but the most impressive experience is off San Juan Island's west coast, where some 80 orcas prowl the waters during salmon season each summer. If money is no object, book the stunning, three-bedroom Seas the Day, a rental perched on a rock above the Haro Straits ($990 per night, $225 cleaning fee). Paddle through crowds of killer whales—don't worry, they're only after the salmon—on a one-day sea kayak trip with Outdoor Odysseys ($95 per person). Later, venture into town for applewood-smoked oysters at Duck Soup Inn.
Baltimore; Pittsburgh; Washington, D.C.: Laurel Highlands, Pa.
Driving time: 4 hrs., 1.5 hrs., and 3.5 hrs., respectively
A patchwork of picturesque forests and country clubs, the Laurel Highlands was once the hunting and fishing playground of Industrial Revolution-era barons. It's now better known for a few of Frank Lloyd Wright's best works, like Fallingwater and the cypress-and-sandstone Kentuck Knob. Rent your own Wright for a weekend at Polymath Park Resort: The 100 acres contains Duncan House, a one-story ranch built in 1957 ($425 per night, two-night minimum). Bring your fly rod to fish the teeming trout streams nearby.
Denver: Grand Lake, Colo.
Driving time: 2 hrs.
The best jumping-off point for exploring Rocky Mountain National Park—while avoiding the tourists in Estes Park—is Bear Crossing, a secluded three-bedroom cabin on the western banks of Grand Lake. It has a boat dock as well as a jaw-dropping view of Shadow Mountain ($475 per night, two-night minimum). Spend a day or two exploring the alpine tundra atop Flattop Mountain and taking in views of Ptarmigan Glacier with a local guide from Kaiyote Tours ($180, full day). When your legs are eventually burned out from all the hiking, rent a Sea-Doo speedboat at Trail Ridge Marina ($250 for four hours) and search for osprey; these beautiful hawks fish for rainbow trout in these waters.