120+ Private Villas and Holiday Rentals in Old Town Winchester |
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  2. Virginia
  3. Winchester
  4. Old Town Winchester

Old Town Winchester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Old Town Winchester

Discover more than 120 vacation rentals available in Old Town Winchester. 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 Old Town Winchester.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Town Winchester, 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 Old Town Winchester. On average, places to stay near Old Town Winchester offer 694.7 ft², with nightly prices averaging GB £122.

With Casai, finding and comparing holiday rentals in Old Town Winchester 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 Old Town Winchester

Type Count
Holiday Apartments 33
Vacation Homes 32
Cottages 1
Villas 1

Use these Quick Filters to Find a Holiday Rental in Old Town Winchester

★ 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 Old Town Winchester.

Weather in Old Town Winchester, VA

View the weather forecast for Old Town Winchester before booking your Old Town Winchester 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 Old Town Winchester, VA

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


SheNonedoah Valley Discovery Museum
Handley Regional Library
Bright Box Theater
George Washington's Office
Old Court House Civil War Museum
Hollywood Casino at Charles Town Races
SheNonedoah University
Winchester Medical Center
George Washington National Forest
Bluemont Vineyard
Summit Point Raceway
Dinosaur Land
Apple Blossom Mall
Charles Town Library
Mt Hebron Cemetery
Jim Barnett Park
Wilson's Wild Animal Park
Patsy Cline Historic House
Twin Oaks Tavern Winery
Blue Ridge Arts Council and Gallery

Other Places to Stay in Old Town Winchester, VA


Winchester 370 Properties
Bright Box Theater 114 Properties
Old Court House Civil War Museum 114 Properties
Shenandoah Valley Discovery Museum 114 Properties
George Washington's Office 114 Properties
Handley Regional Library 113 Properties

Frequently Asked Questions About Old Town Winchester?

What are the top holiday rentals in Old Town Winchester?

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

How many holiday rentals have private pools in Old Town Winchester?

Discover a selection of holiday rentals with private pools near Old Town Winchester 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 Old Town Winchester are best for families?

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

How many Casai.uk holiday rentals are available in Old Town Winchester?

As of 2025, Casai boasts over 120 properties listed in the Old Town Winchester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Town Winchester.


People Also Ask

There are 120 Old Town Winchester, VA Holiday Rentals

Recently Booked Holiday Rentals in Old Town Winchester