117+ Hotel & Resort Deals in Old Town Winchester |
  1. USA
  2. Virginia
  3. Winchester
  4. Old Town Winchester

Old Town Winchester Hotels, Resorts, and Rentals

About Old Town Winchester Vacation Rentals

There are more than 117 places to stay in Old Town Winchester that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Old Town Winchester.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Old Town Winchester, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Old Town Winchester. Places to stay near Old Town Winchester are 620.51 ft² on average, with prices averaging ZA R2,881 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Old Town Winchester with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Old Town Winchester

Type Count
Holiday Apartments 31
Vacation Homes 31
Cabin Rentals 1
Cottages 1
Villas 1

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

★ Pro Tip: Hotala.co.za has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay 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

Stay Near Old Town Winchester's Top Attractions

Hotala.co.za can help you find hotels, resorts, and rentals near many of Old Town Winchester's top attractions, neighborhoods, and points of interest.


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 Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Winchester 361 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 hotels or resorts in Old Town Winchester?

You have a lot of choices in or near Old Town Winchester. If you need a hotel in the Old Town Winchester area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Old Town Winchester:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 117 in the Old Town Winchester area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Old Town Winchester.


People Also Ask

There are 51 hotels in Old Town Winchester and 64 rentals

Recently Booked Hotels, Resorts, or Rentals in Old Town Winchester