Winter Vacation Rentals

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Vacation Rentals in Winter

Custom-Built Log Cabin Family Friendly home on Round Lake, close to trails!

Hayward WI

Located in Hayward, this vacation home is on the waterfront, a 2-minute drive from Round Lake and 9 minutes from Tiger Cat Flowage.

Kitchen

Washer

Breezy Bay Beach On Round Lake

Hayward WI

Located in Hayward, this vacation home is on the waterfront, a 1-minute drive from Round Lake and 6 minutes from Sevenwinds Casino.

Kitchen

Washer

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Winter WI

With a stay at this vacation home in Winter, you'll be on the waterfront, just a 1-minute walk from South Barber Lake and 7 minutes by foot from Barber Lake.

Kitchen

Washer

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

Ojibwa WI

Located in Ojibwa, this vacation home is a 1-minute drive from Ojibwa State Park and 8 minutes from Doc Smith Park.

Kitchen

Free WiFi

Spruce Haven on Round Lake - Summer 2026 weeks available

Hayward WI

Located in Hayward, this vacation home is near the bay, a 1-minute drive from Round Lake and 9 minutes from Sevenwinds Casino.

Kitchen

Washer

Long Lake Retreat in Phillips, Wisconsin

Phillips WI

Located in Phillips, this vacation home is on the waterfront, a 5-minute drive from Lidice Memorial and 8 minutes from Wisconsin Concrete Park.

Kitchen

Washer

Ultimate Hayward Trailhead Cabin

Hayward WI

Located in Hayward, this vacation home is in a rural location, a 1-minute drive from Round Lake and 8 minutes from Spider Lake Townhall.

Kitchen

Washer

Spacious 5-bedroom house in serene Clam Lake with WiFi

Clam Lake WI

With a stay at this vacation home in Clam Lake, you'll be just steps from Chequamegon National Forest and Upper Clam Lake.

Kitchen

Washer

The Gathering Place, 3 BR sleeps 8, Near Hayward close to lakes and trails.

Hayward WI

With a stay at this vacation home in Hayward, you'll be steps from Chequamegon National Forest and a 1-minute drive from Lost Land Lake.

Kitchen

Washer

Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

Hayward WI

Located in Hayward, this vacation home is on the waterfront, a 4-minute drive from Tiger Cat Flowage and 6 minutes from Spider Lake Townhall.

Kitchen

Washer

Paradise Shores & Fish Galore ~your own private beach & dock!

Cable WI

When you stay at this vacation home in Cable, you'll be on the waterfront, just steps from Chequamegon National Forest and Lake Namakagon.

Big Chip Outdoors - 4 bedroom house with WiFi & AC in Heart of Chippewa Flowage

Hayward WI

When you stay at this vacation home in Hayward, you'll be within a 10-minute drive of Glover Lake and Ghost Island.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.