120+ Luxury Vacation Rentals & Cabins in Old Town Winchester |
  1. USA
  2. Virginia
  3. Winchester
  4. Old Town Winchester

Old Town Winchester Cabin Rentals

About Old Town Winchester Vacation Rentals

There are more than 120 incredible getaway rentals that are available in Old Town Winchester. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Old Town Winchester.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Old Town Winchester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Old Town Winchester. Places to stay near Old Town Winchester are 739.55 ft² on average, with prices averaging US $162 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Old Town Winchester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Old Town Winchester

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

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

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Old Town Winchester with Cabinns.com.

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

Activities Old Town Winchester Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Old Town Winchester. Discover Top Attractions For Your Next Outdoor Adventure.


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

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Winchester 471 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

Complexes around Old Town Winchester, VA


Country Inn 3 Properties
Days Inn 3 Properties
Fairfield Inn 3 Properties
Hampton Inn Winchester 3 Properties
Holiday Inn Winchester Gateway Ihg Hotel 3 Properties
Quality Inn 3 Properties
Red Roof Inn Winchester Va 3 Properties
The George Washington Wyndham Grand Hotel 3 Properties
Towneplace 3 Properties
Travelodge 3 Properties
Wingate 2 Properties

Frequently Asked Questions About Old Town Winchester?

What are the top cabins, lake houses & summer homes in Old Town Winchester?

We provide an array of great vacation destinations in Old Town Winchester. If you are looking to stay in or around the Old Town Winchester area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Old Town Winchester:

How many cabin rentals and resorts have private pools in Old Town Winchester?

We have 9 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Old Town Winchester. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Old Town Winchester is best for families?

Searching for a family-friendly cabin in Old Town Winchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Old Town Winchester?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 120 in the Old Town Winchester area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Old Town Winchester.


People Also Ask

There are 51 hotels in Old Town Winchester and 67 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Old Town Winchester