Discover winter rentals Winona - We found 78 exact matches
About Winona Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Winona, MO 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 Winona. 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 Winona and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Winona Winter Rentals
What are the top rated Winter Rentals in Winona?
There are a lot of options in Winona. If you plan on staying in the Winona area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Winona:
- Unique cabins in the woods Not friendly for Street Bikes.
- Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
- Private Hilltop Cabin Near Current River
- Cabin in the heart of the Ozark National Scenic Riverway!
- Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
- Ozark Oasis 3 B/3 B in Eminence with Spectacular View!
- ⭕️Van Buren 3 Bedroom Home Near The Landing with an Arcade! Fast Wifi!
- Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!
- RockStack Retreat @ Eminence, MO
- Newly renovated early 1900’s farmhouse
How much does it cost to rent a place to stay near Winona in the wintertime?
The average cost for winter rentals in Winona is $274 per night. Vacation Cottage has a wide list of great winter places to stay near Winona that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Winona that allow pets?
Yes, here are the top cottage/chalet rentals in Winona that allow you to bring your pet or dog:
- Private Hilltop Cabin Near Current River
- Living Waters Estates 1
- Cabin in the heart of the Ozark National Scenic Riverway!
- 1 Mi to Current River Sunset-View Van Buren Cabin
See all pet-friendly vacation rentals in Winona on Vacation Cottage
Do you have any winter rentals in Winona that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Winona to find what works for you.
Are there winter accommodations in Winona that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 78 private swimming pools or indoor pools accommodations near Winona along with other great amenities.
Do any winter holiday rentals in Winona have hot tubs?
About 78 holiday rentals in Winona boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Winona?
Yes, there are many luxury places to stay in Winona for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Winona with all the best amenities for your next trip.
