50+ Rental Villas and Private Getaways in Upperville |
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  2. Virginia
  3. Upperville

Upperville Vacation Rentals & One Degree Stays Homes

About Upperville Vacation Rentals

There are more than 50 vacation rentals that are available in Upperville. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Upperville.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Upperville, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Upperville. Places to stay near Upperville are 1356.07 ft² on average, with prices averaging US $650 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Upperville with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Upperville

Type Count
Vacation Homes 27
Cottages 9
Villas 2

Use these Quick Filters to Find a Vacation Rental in Upperville

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Upperville.

Weather in Upperville, VA

View the weather forecast for Upperville before booking your Upperville Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Upperville, VA

OneDegreeStays offers a large selection of top attractions around Upperville. Research things to do on your vacation before you visit Upperville.


SheNonedoah University
Leesburg Corner Premium Outlets
Front Royal Entrance SheNonedoah National Park
Stone Tower Winery
Bluemont Vineyard
Summit Point Raceway
Skyline Caverns
Dinosaur Land
Village at Leesburg
Apple Blossom Mall
Tally Ho Theatre
Tudor Day Spa
Morven Park
Cobbler Mountain Cellars
Breaux Vineyards
Greenhill Winery & Vineyards
Barrel Oak Winery
Chrysalis Vineyards
Linden Vineyards

Frequently Asked Questions About Upperville?

What are the top vacation 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 Vacation Rentals in Upperville:

Which vacation homes in Upperville are best for families?

If you are looking for a family-friendly vacation home in Upperville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upperville:

How many onedegreestays vacation rentals are available in Upperville?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 50 in the Upperville area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Upperville. 


People Also Ask

There are 50 Upperville, VA Vacation Rentals

Recently Booked Vacation Rentals in Upperville