49+ Private Villas and Holiday Rentals in Upperville |
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  3. Upperville

Upperville Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Upperville

Discover more than 49 vacation rentals available in Upperville. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upperville.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upperville, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upperville. On average, places to stay near Upperville offer 1383.75 ft², with nightly prices averaging GB £468.

With Casai, finding and comparing holiday rentals in Upperville is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Upperville

Type Count
Vacation Homes 27
Cottages 9
Villas 2

Use these Quick Filters to Find a Holiday Rental in Upperville

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal 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

Casai 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 holiday rentals in Upperville?

With numerous options available in Upperville, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upperville:

Which holiday homes in Upperville are best for families?

If you're searching for a family-friendly holiday home in Upperville, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upperville:

How many Casai.uk holiday rentals are available in Upperville?

As of 2025, Casai boasts over 49 properties listed in the Upperville area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upperville.


People Also Ask

There are 49 Upperville, VA Holiday Rentals

Recently Booked Holiday Rentals in Upperville