509+ Private Villas and Holiday Rentals in Wintergreen |
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  2. Virginia
  3. Charlottesville
  4. Wintergreen

Wintergreen Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Wintergreen

Discover more than 509 vacation rentals available in Wintergreen. 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 Wintergreen.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Wintergreen, 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 Wintergreen. On average, places to stay near Wintergreen offer 862.95 ft², with nightly prices averaging GB £249.

With Casai, finding and comparing holiday rentals in Wintergreen 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 Wintergreen

Type Count
Vacation Homes 200
Holiday Apartments 38
Cottages 5

Use these Quick Filters to Find a Holiday Rental in Wintergreen

★ 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 Wintergreen.

Weather in Wintergreen, VA

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

December - February
High 57°F       Low 27°F
March - May
High 72°F       Low 32°F
June - August
High 86°F       Low 59°F
September - November
High 76°F       Low 34°F

Top Attractions Around Wintergreen, VA

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


Wintergreen Resort
Blue Ridge Parkway North Entrance
George Washington National Forest
Bold Rock Hard Cider Nellysford Cidery
Walton's Mountain Museum
Mary Baldwin College
Pippin Hill Farm & Vineyards
Rockfish Gap Entrance SheNonedoah
Afton Mountain Vineyards
Crabtree Falls
Sherando Lake Recreation Area
Frontier Culture Museum
Veritas Vineyard and Winery
The Woodrow Wilson Presidential Library
Starr Hill Brewery
Zeus Digital Theater
Cardinal Point Vineyard and Winery
Staunton Public Library
Wayne Theatre
American Shakespeare Center

Other Places to Stay in Wintergreen, VA


Wintergreen Resort 62 Properties
Treeloft 32 Properties
Pedlars Edge 30 Properties

Frequently Asked Questions About Wintergreen?

What are the top holiday rentals in Wintergreen?

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

How many holiday rentals have private pools in Wintergreen?

Discover a selection of holiday rentals with private pools near Wintergreen with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Wintergreen are best for families?

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

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

As of 2025, Casai boasts over 509 properties listed in the Wintergreen area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Wintergreen.

Nearby Neighborhood (2) 
Neighborhood Property Count
Treeloft Vacation Rentals in Charlottesville, Virginia 32
Pedlars Edge Vacation Rentals in Charlottesville, Virginia 30

People Also Ask

There are 509 Wintergreen, VA Holiday Rentals

Recently Booked Holiday Rentals in Wintergreen