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Featured Old Town Winchester Family Hotels

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
The George Washington Hotel, A Wyndham Grand Hotel
See all 351 properties in Old Town Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels with Pools in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,000 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on Mar 31, 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 351 properties in Old Town Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels With Connecting Rooms in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
The George Washington Hotel, A Wyndham Grand Hotel
See all 351 properties in Old Town Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.