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Jackie Leonhard bought her first Northwoods rental home, now known as Lake Mohawksin Lodge, out of foreclosure in 2016. “I have great memories of this property. We would pass it every year when my family came Up North,” recalls Leonhard, owner of Northwoods Community Realty in Tomahawk. “It was a good time to invest. People still trying to recover from the 2008 economic downturn were unloading their properties for the money.”
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Leonard now owns or manages seven rental properties in the area, and she’s far from alone in getting into the short-term rental game. Nine years ago, “there were maybe 10 other listings in the Tomahawk area on Vrbo and Airbnb,” she says. “I checked today and there are 300.”
That kind of growth in the market for rentals in Wisconsin’s Northwoods has given vacationers more choices than ever. As an example, the Eagle River Airbnb market experienced one-year growth of 149%, according to 2025 data from Smith Travel Research.
But two factors may impede growth at its present pace: Competition and cost of entry – waterfront home prices in the Northwoods have doubled since the pandemic. “My bookings are about 20% down,” Leonhard says. “But I can deal with it. My properties have doubled in value since I bought them.”
Angie McGuire and her husband made their investment early in the pandemic, first moving from Dodgeville to the Northwoods just as the housing market was starting to take off. Then they bought another home near Eagle River and did extensive renovation to convert it to a rental property, Dollar Lake Retreat. “I lost my job and convinced my husband it was time for a change,” McGuire says. “We talked about how great it would be to open a resort Up North and made it happen.”
The McGuires are happily holding their own; the five-bedroom property is booked far out for peak season. “We have repeat customers now, which is great,” she says. “We love it here and are making it work.”
Leonhard, though, thinks the window to get into the market may have closed for all but the best-financed buyers. “I really feel for investors who are paying top dollar and have a mortgage,” she says. “They may need every booking just to cover their payments.”
The McGuires feel lucky to have made their dream come true. “If we had waited, I don’t think we would have been able to do it,” Angie says. “Not with home prices the way they are.”
5 Cabins for Rent in Wisconsin
Go rustic or glam it up. Whether you’re looking for a few standout choices or just shopping comps, your search for a cabin to rent Up North starts here. Each has a 5-star review on Airbnb, and prices are based upon our search criteria of identical late summer dates for a week away. Now that’s a vacation!
Northwoods Log Home
DUNBAR, MARINETTE COUNTY | $2,685/SEVEN NIGHTS | UP TO 7 GUESTS
When it comes to log cabins, this is the real deal. The two-bedroom house sits on a hilltop overlooking Young Lake, amid the area’s dense forests and waterfalls. You will feel a world away, wrapped in the cabin’s cozy ambiance and beautiful setting.
Adelaide Adventure House
WINCHESTER, VILAS COUNTY | $2,095/SEVEN NIGHTS | UP TO 6 GUESTS
The exterior of this home just 3 miles from the Michigan border reads like a quaint cottage. Inside, you’ll feel the warmth of a classic but updated log cabin. The active adventurer will enjoy direct access to hundreds of miles of ATV/UTV and snowmobile trails. Lake Adelaide is just a short walk away.
‘Tree top’ Log Cabin
HILES, FOREST COUNTY | $3,623/SEVEN NIGHTS | UP TO 8 GUESTS
This serene hideaway is nestled into a hillside, so the tree tops rustle outside your window. The century-old cabin with a new addition offers a unique blend of rustic charm and modern updates. Swim, boat or fish on Pine Lake, or hike the nearby trails.
Modern Luxury Lake House
WEBSTER, BURNETT COUNTY | $4,182/SEVEN NIGHTS | UP TO 8 GUESTS
This dreamy lake home built in 2024 is perfect for a pampered getaway. Its Scandinavian design is crisp and clean, and every room is appointed with luxurious amenities. Enjoy crystal-clear Lake Benoit, and nearby hiking and snowmobile trails. End the day soaking in a wood-burning sauna under the stars.
Lakeside A-Frame
PHILLIPS, PRICE COUNTY | $1,039/SEVEN NIGHTS | UP TO 4 GUESTS
Looking for some peace and quiet? This A-frame on Musser Lake is the ticket; a small, beautifully kept retreat. The lake is known for muskie, so bring a heavy rod and reel, or kayak on the glassy water. Observe wildlife from the home’s deck or explore the nearby Chequamegon-Nicolet National Forest.
