What are the top rated Pet Friendly Vacation Rentals in Old Town Winchester?

There are a lot of options in Old Town Winchester. If you plan on staying in the Old Town Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Pet Friendly Vacation Rentals in Old Town Winchester: <a href="/property/la-quinta-inn-suites-by-wyndham-winchester/EP-2678524" class="class="static-page-link"">La Quinta Inn &amp; Suites by Wyndham Winchester</a> <a href="/property/tru-by-hilton-winchester-va/BC-5637894" class="class="static-page-link"">Tru By Hilton Winchester, Va</a> <a href="/property/quality-inn-winchester/BC-327920" class="class="static-page-link"">Quality Inn Winchester</a> <a href="/property/spark-by-hilton-winchester/BC-327879" class="class="static-page-link"">Spark By Hilton Winchester</a> <a href="/property/hampton-inn-winchester-university-mall/BC-191097" class="class="static-page-link"">Hampton Inn Winchester-University/Mall</a> <a href="/property/microtel-inn-suites-by-wyndham-winchester/BC-7902424" class="class="static-page-link"">Microtel Inn &amp; Suites by Wyndham Winchester</a> <a href="/property/holiday-inn-winchester-southeast-historic-gateway-by-ihg/BC-311433" class="class="static-page-link"">Holiday Inn Winchester Southeast-Historic Gateway by IHG</a> <a href="/property/hilton-garden-inn-winchester/BC-173393" class="class="static-page-link"">Hilton Garden Inn Winchester</a> <a href="/property/country-inn-suites-by-radisson-winchester-va/BC-513115" class="class="static-page-link"">Country Inn &amp; Suites by Radisson, Winchester, VA</a> <a href="/property/candlewood-suites-winchester-by-ihg/BC-349477" class="class="static-page-link"">Candlewood Suites Winchester by IHG</a>

How many pet-friendly vacation rentals are available in Old Town Winchester on Wintersvacationsrentals?

There are more than 44 pet-friendly rentals available on Wintersvacationsrentals. Check prices and availability in Old Town Winchester and last updated on December 2025. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in Old Town Winchester?

There are many dog-friendly vacation homes available in Old Town Winchester. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Old Town Winchester: Indigo Blue modern open vibe on tree lined street Luxury 4BR Retreat Kitchen Grill Fireplace Cleveland Park awesome Winchester 2 BR 1st fl napt. walk to everything! Luxury Retreat w/Chef's Kitchen Grill & Fireplace

Do you have any luxury vacation homes that allow pets in or near Old Town Winchester?

Most definitely! There are many luxury places to stay in Old Town Winchester. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Old Town Winchester. Though note, more expensive is not always better.