Happy Holidays: where to get deals on vacation homes

The next Prince Edward County
Trent Hills

What you’ll pay: A 22-acre farm with a drive-shed and four-bedroom farmhouse was recently listed for $259,000. From Toronto: 180 km (3 hours by car)

Northumberland farm country is experiencing an artis­anal renaissance. In tiny Warkworth, for example, quirky toy shops and indie cafés have recently joined the century-old general store. The region still exudes a rustic charm, though: gracious homes, bucolic pastures, Amish bakers selling pie along Tuftsville Road, and, in nearby Stirling, a couple offering horse-driving lessons—perfect training for the would-be gentleman farmer.

The next Wasaga Beach
Crystal Beach

What you’ll pay: A New England–style former boarding house and separate cottage recently went on the market for $299,000. From Toronto: 160 km (3 hours by car)

A hundred years ago, Crystal Beach attracted vacationers and vaudevillians to the eastern shores of Lake Erie with its roller coasters, raucous dance halls and waffle stands. Now the village is a resort town, with a new yoga studio, condo developments and an influx of urban refugees. (The owners of the upscale bridal salon Lowon Pope run a vintage shop on the main drag.) One thing that hasn’t changed: the aptly named white-sand beach.

The next Georgian Bay
Eastern Kawarthas

What you’ll pay: A three-bedroom, chalet-style cottage on Mississagua Lake was recently listed for $589,000. From Toronto: 200 km (3 hours by car)

The Kawarthas offer the holy trinity of Ontario cottage life: fishing, canoeing and boating. Prices can run as high as $2 million in areas like Stoney Lake, but the eastern lakes—Kasshabog, Oak, Chandos—offer better value and the same serene landscape of rocky shores, pines and maples. Most properties are road-accessible, so extroverts can still hightail it to Peterborough for the summer-long Little Lake Musicfest if they get stir-crazy.

The next Mont Tremblant
Le Massif, Quebec

What you’ll pay: Three-bedroom, 2,300-square-foot chalets are currently selling for $640,000. From Toronto: 900 km (1.5 hours by plane)

Daniel Gauthier, the co-founder of Cirque du Soleil, spent $230 million transforming Le Massif, a Charle­voix mountain overlooking the St. Lawrence River, into a lavish ski resort. In addition to an eco-lodge and farm-to-table restaurant, he built 64 chalets at the summit and 11 riverfront homes at the base, all with lofty ceilings and ski-in access. As for the hill: 52 runs, prodigious powder and Canada’s steepest vertical east of the Rockies.

The next Scottsdale
Pinehurst, North Carolina

What you’ll pay: A three-bedroom cottage across the street from the fifth tee on Pinehurst’s No. 5 fairway was recently listed at $374,000. From Toronto: 1300 km (2 hours by plane)

Snowbound golfers dreaming of white visors and freshly mown greens should consider getting a winter home in Pinehurst. The epony­mous resort is the oldest in the U.S., and there are more than 40 courses within a 20-minute drive. The idyllic village is loaded with button-cute homes, but hard-core links enthusiasts looking to perfect their backswing can also set up house right on the fairway.

The next Fort Lauderdale
Fort Myers Beach, Florida

What you’ll pay: A three-bedroom gulf-view condo was recently listed at $349,000. From Toronto: 2500 km (3 hours by plane)

Occupying the tiny island of Estero off the Florida Gulf Coast, Fort Myers Beach is lined with 12 kilometres of white beach, where manatees, pelicans and dolphins make daily appearances. Affordable waterfront condos provide quick access to the beach and Sanibel Island, an affluent oasis of shell beaches and wildlife reserves, where a bylaw prohibits buildings from outstretching the palm trees.