Upperville Ski Chalets Rentals & Holiday Homes

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 Ski Chalet Rentals in Upperville:

• Lovely Guest House 2.5 miles from downtown Middleburg
• Historic house in Upperville! Wineries, equestrian events, great location!
• Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
• Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
• Historic home with 7 BR near Middleburg, VA in Piedmont horse country
• Mountain View + Hot tub + Sauna + Yoga + Trails + Wineries + Geodesic stargazing dome
• Ashby Inn & Restaurant
• Welcoming farmhouse on 10 quiet acres ~10 min from Middleburg
• Serene Farmhouse and former winery on 44 acres of rolling hills.
• Middleburg address - Charming Cottage with super location in country setting

There are many ski chalets available in Upperville; however, here are the most popular ski chalets listed in Upperville:

• Blue Mountain Log Cabin
• Historical Paris Cabin on Farm with Fire Pit!
• Grand 9BR Provenance Manor Ideal for Gatherings
• Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Luxurycruises offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Upperville.

At Luxurycruises most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Upperville to find what works for you.

Yes, there are 52 self-catering family ski chalet in Upperville that have hot tubs & other amenities.