Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 68%

Airbnb, Vacation rentals and hotel deals in Winter, WI

10 (14 reviews)
"Upscale Accommodations" with an "Up North" location!
Resort · 2 Guests · 1 Bedroom
$200 /night*
View deal
9.8 (19 reviews)
Family log home nestled in the woods just minutes from trails.
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
View deal
10 (9 reviews)
Beautiful Private Chippewa Flowage Lake Home September - May Discounts
Holiday home · 2 Guests · 1 Bedroom
$375 /night*
View deal
9.4 (50 reviews)
Charming 2 beds, 1 bath, and a loft with a lake front view and shoreline
Cabin · 2 Guests · 1 Bedroom
$250 /night*
View deal
9.8 (22 reviews)
Echo Point Retreat on the Beautiful Tiger Cat Flowage
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
View deal
10 (55 reviews)
Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
Holiday home · 2 Guests · 1 Bedroom
$399 /night*
View deal
10 (7 reviews)
On the Edge of the Water-The Edgewater!
Cabin · 2 Guests · 1 Bedroom
$150 /night*
View deal
Lucky Charlie Lodge 3 Bedroom Home by Redawning
Holiday home · 2 Guests · 1 Bedroom
$375 /night
View deal
10 (3 reviews)
Welcome to The Hideaway on Highland.
Cabin · 2 Guests · 1 Bedroom
$225 /night*
View deal
9.4 (19 reviews)
Family Lake Retreat on Lac Courte Oreilles
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
View deal
9.0 (13 reviews)
Book your summer cabin now! Between 2 Great Lakes outside of Hayward!
Cabin · 2 Guests · 1 Bedroom
$150 /night*
View deal
10 (2 reviews)
Cozy family-friendly A-frame on sandy beachfront - dogs welcome!
Cabin · 2 Guests · 1 Bedroom
$250 /night*
View deal
9.8 (118 reviews)
Cozy Lake Home Near Hayward! Close Trails, Fishing, Fun Await!
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
View deal
9.8 (27 reviews)
4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
Holiday home · 2 Guests · 1 Bedroom
$170 /night*
View deal
10 (47 reviews)
Rustic, Cozy, Northwoods Cabin steps away from Round Lake on Richardson Bay!
Cabin · 2 Guests · 1 Bedroom
$249 /night*
View deal
10 (59 reviews)
Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
Cottage · 2 Guests · 1 Bedroom
$299 /night*
View deal
9.8 (57 reviews)
YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
Cabin · 2 Guests · 1 Bedroom
$129 /night*
View deal
10 (14 reviews)
Spacious Northwoods Cabin with Amazing Game Room
Cabin · 2 Guests · 1 Bedroom
$225 /night*
View deal
9.6 (24 reviews)
Custom built Home on Round Lake
Holiday home · 2 Guests · 1 Bedroom
$600 /night*
View deal
9.8 (59 reviews)
Secluded Hayward Cabin
Cabin · 2 Guests · 1 Bedroom
$215 /night*
View deal

Airbnb, Holiday Lakefront Log Cabin Rentals with Fireplace, and Other Rental Options in Winter, WI

9.0 (13 reviews)
Book your summer cabin now! Between 2 Great Lakes outside of Hayward!
Cabin · 2 Guests · 1 Bedroom
$150 /night*
View deal
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
Cabin · 2 Guests · 1 Bedroom
$250 /night*
View deal
9.2 (35 reviews)
Beautiful Craftsman Style Lake Home
Cabin · 2 Guests · 1 Bedroom
$750 /night*
View deal
What Are The Most Popular Amenities in Winter, WI?
Top Rental Amenities in Winter, WI
+
Check above for the most common and the least popular rental amenities in Winter, and pick the one that fits your preference easily. In Winter, 180 rentals offer TV, 172 rentals offer Bed linens provided, 168 rentals offer Parking Available. So, if you need TV during your vacation, use the TV filter to compare these properties. Two amenities that are not typical are Pool, Hot Tub.

What is the Best Time to Rent a Cabin in Winter, WI?

Tips to Rent Cabins (Stay for a Week) for Cheapest Price in Winter, WI

Low Season
December
Most affordable month to stay
$80
Average rate of the cheapest cabin option in low season month
High Season
July
Peak month to stay
$1,900
Average rate of the cheapest stay option in high season month
$1,900
Jul
$140
Aug
$113
Sep
$112
Oct
$88
Nov
$80
Dec
$92
Jan
$101
Feb
$104
Mar
$110
Apr
$111
May
$112
Jun
$130
Sun
$150
Mon
$2,300
Tue
$226
Wed
$2,033
Thu
$1,900
Fri
$1,900
Sat
Cheapest day of week
Sunday
Cabin price normally the lowest on this day
$130
is the cheapest nightly rate for cabin on this day
Highest day of week
Tuesday
Most expansive day to book a cabin
$2,300
is the highest nightly rate for cabin on this day
Which Price Range Is Considered As A Good Deal in Winter, WI Area?
Vacation Cabin & House Rental Price Information in Winter, WI
+
The graph shows the percentages of vacation homes in each price bucket. Winter has the largest percentage (28.04%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Most Liked Rental Accommodations in Winter, WI?
Rental Property Types in Winter, WI
+
Before visiting Winter, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: Cabin, House, Resort, Cottage, Lodge, Chalet, Mobile Home, Condo, Chateau / Country House. Cabin is the most-liked rental type, with the largest percentage of 45.26%. The biggest home in this area available for rent is around 4800 square feet.The least popular accommodation in Winter is Chateau / Country House rentals
How Many Accommodations Are Pets Allowed in Winter, WI?
Percentage of Pet Friendly Rental Properties in Winter, WI
+
35.79% of vacation homes in Winter are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Best Tourist Attractions in Winter, WI?
Must Visit Places In Winter, WI
+

The most common & popular places (a.k.a points of interests) here in Winter are:

Must-Visit Trails in Winter, WI?
Must Visit Trails In Winter, WI
+
The most visited trails here in Winter are: Trego Nature Trail, Birkebeiner Trail, Phipps Fire Lane, Black Lake Trail, Spring Creek Trail, Kickapoo Trail, Pigeon Lake Trail, Morgan Falls and St Peter's Dome Trail, Marengo River and Porcupine Lake via North Country Trail, Copper Falls State Park Loop Trail.
Best Campgrounds in Winter, WI?
Campgrounds Recommendations In Winter, WI
+
For campgrounds in Winter, here are our recommendations: Two Lakes Campground, East Twin Campground, Lake Chippewa Campground, Hayward KOA, Mineral Lake Campground, Day Lake Campground, Moose Lake Campground, Black Lake Campground, Stockfarm Bridge Campground, Pine Lake Campground.

Airbnb, Holiday Lakefront Log Cabin Rentals with Air Conditioning, and Other Rental Options in Winter, WI

Fall Getaway Resort-3 KING suites, Dog-Friendly
Chalet · 2 Guests · 1 Bedroom
$256 /night
View deal

Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Winter, WI

9.2 (35 reviews)
Beautiful Craftsman Style Lake Home
Cabin · 2 Guests · 1 Bedroom
$750 /night*
View deal
9.4 (50 reviews)
Charming 2 beds, 1 bath, and a loft with a lake front view and shoreline
Cabin · 2 Guests · 1 Bedroom
$250 /night*
View deal
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
Cabin · 2 Guests · 1 Bedroom
$250 /night*
View deal

Airbnb, Pet Friendly Vacation House in Winter, WI

Fall Getaway Resort-3 KING suites, Dog-Friendly
Chalet · 2 Guests · 1 Bedroom
$256 /night
View deal
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers