Douglas County Winter Rentals & Holiday Homes

Discover winter rentals Douglas County - We found 174 exact matches

10.0 (197 Reviews)
2 Bedrooms 4 Guests
|
10.0 (2 Reviews)
2 Bedrooms 6 Guests
From US $96 per night
|
7.8 (76 Reviews)
1 Bedroom 2 Guests
10.0 (108 Reviews)
2 Bedrooms 5 Guests
|
9.8 (6 Reviews)
2 Bedrooms 6 Guests
10.0 (84 Reviews)
2 Bedrooms 100 Guests
|
8.2 (4 Reviews)
3 Bedrooms 10 Guests
From US $324 per night
10.0 (31 Reviews)
2 Bedrooms 8 Guests
|
8.0 (3 Reviews)
3 Bedrooms 6 Guests
10.0 (26 Reviews)
1 Bedroom 2 Guests
6.8 (142 Reviews)
75 Bedrooms 6 Guests
10.0 (11 Reviews)
2 Bedrooms 4 Guests
10.0 (2 Reviews)
2 Bedrooms 26 Guests
From US $230 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
9.8 (106 Reviews)
1 Bedroom 2 Guests
9.8 (74 Reviews)
1 Bedroom 5 Guests
From US $195 per night
9.8 (63 Reviews)
2 Bedrooms 8 Guests
9.8 (37 Reviews)
1 Bedroom 4 Guests
9.8 (29 Reviews)
1 Bedroom 4 Guests
9.8 (23 Reviews)
1 Bedroom 4 Guests

About Douglas County Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in Douglas County, WI perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.

Vacation Cottage presents luxury options for travelers seeking to rent a place in Douglas County. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Douglas County and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Douglas County Winter Rentals

What are the top rated Winter Rentals in Douglas County?

There are a lot of options in Douglas County. If you plan on staying in the Douglas County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Douglas County:

How much does it cost to rent a place to stay near Douglas County in the wintertime?

The average cost for winter rentals in Douglas County is $307 per night. Vacation Cottage has a wide list of great winter places to stay near Douglas County that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Douglas County that allow pets?

Yes, here are the top cottage/chalet rentals in Douglas County that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Douglas County on Vacation Cottage

Do you have any winter rentals in Douglas County that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Douglas County to find what works for you.

Are there winter accommodations in Douglas County that have indoor swimming pools?

As of 2025, the data from Vacation Cottage shows that there are over 174 private swimming pools or indoor pools accommodations near Douglas County along with other great amenities.

Do any winter holiday rentals in Douglas County have hot tubs?

About 174 holiday rentals in Douglas County boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in Douglas County?

Yes, there are many luxury places to stay in Douglas County for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Douglas County with all the best amenities for your next trip.