Door County Winter Rentals & Holiday Homes

Discover winter rentals Door County - We found 1396 exact matches

Barrel Sauna Luxury Walk to Northern Haus
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10.0 (5 Reviews)
4 Bedrooms 12 Guests
Chanticleer Guest House
FromUS $284 per night
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10.0 (185 Reviews)
1 Bedroom 2 Guests
Door County Family Home 3 Mi Whitefish Dunes
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10.0 (3 Reviews)
3 Bedrooms 6 Guests
The Sweet Retreat by Simple Life Rentals
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10.0 (3 Reviews)
3 Bedrooms 8 Guests
Wild Cedars - Cana Island - Lake Michigan - Amazing new home
10.0 (218 Reviews)
2 Bedrooms 7 Guests
Secluded Home Walk to Marina GameRoom & HotTub
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10.0 (2 Reviews)
3 Bedrooms 9 Guests
Remodeled 1938 Log Cabin – Walk to Sister Bay
10.0 (192 Reviews)
2 Bedrooms 5 Guests
Thenells Beach House by Simple Life Rentals
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Carraig Dale Cottage
FromUS $594 per night
10.0 (2 Reviews)
3 Bedrooms 8 Guests
Waterfront Dream Cottage With A Million Dollar View, HARBOR Unit
10.0 (179 Reviews)
1 Bedroom 4 Guests
Harbor House Cottage located in the heart of Ephraim!
10.0 (168 Reviews)
2 Bedrooms 5 Guests
Sister Bay Cozy Cottage, Door County
10.0 (152 Reviews)
2 Bedrooms 4 Guests
Fish Creek Condo/Town Home at Brook Point, Door County
10.0 (138 Reviews)
2 Bedrooms 4 Guests
Door County Cabin in the Woods, Baileys Harbor
10.0 (138 Reviews)
2 Bedrooms 4 Guests
Perfect location! Steps from marina and downtown area!
10.0 (132 Reviews)
1 Bedroom 2 Guests
Prime Location & Highly Rated Dog Friendly Cottage with 'Perks'
10.0 (131 Reviews)
2 Bedrooms 6 Guests

About Door County Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in Door 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, cottages, 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 Door 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 Door County and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Door County Winter Rentals

What are the top rated Winter Rentals in Door County?

There are a lot of options in Door County. If you plan on staying in the Door 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 Door County:

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

The average cost for winter rentals in Door County is $532 per night. Vacation Cottage has a wide list of great winter places to stay near Door 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 Door County that allow pets?

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

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

Do you have any winter rentals in Door 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 Door County to find what works for you.

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

As of 2026, the data from Vacation Cottage shows that there are over 1396 private swimming pools or indoor pools accommodations near Door County along with other great amenities.

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

About 1396 holiday rentals in Door County boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in Door County?

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