Discover winter rentals Upperville - We found 29 exact matches
About Upperville Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Upperville, VA 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 Upperville. 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 Upperville and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Upperville Winter Rentals
What are the top rated Winter Rentals in Upperville?
There are a lot of options in Upperville. If you plan on staying in the Upperville area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Upperville:
- The Mill House in Upperville -
- Middleburg address - Charming Cottage with super location in country setting
- Blue Mountain Log Cabin
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
- Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
- Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
- Historic spacious home in the heart of Upperville, VA
How much does it cost to rent a place to stay near Upperville in the wintertime?
The average cost for winter rentals in Upperville is $623 per night. Vacation Cottage has a wide list of great winter places to stay near Upperville that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Upperville that allow pets?
Yes, here are the top cottage/chalet rentals in Upperville that allow you to bring your pet or dog:
- Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries
- Historical Paris Cabin on Farm with Fire Pit!
- Grand 9BR Provenance Manor Ideal for Gatherings
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
See all pet-friendly vacation rentals in Upperville on Vacation Cottage
Do you have any winter rentals in Upperville that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upperville to find what works for you.
Are there winter accommodations in Upperville that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 29 private swimming pools or indoor pools accommodations near Upperville along with other great amenities.
Do any winter holiday rentals in Upperville have hot tubs?
About 29 holiday rentals in Upperville boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Upperville?
Yes, there are many luxury places to stay in Upperville for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upperville with all the best amenities for your next trip.
