Find Romantic Hotels in Old Town Winchester, VA

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Pick from 1 Old Town Winchester Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The George Washington Hotel, A Wyndham Grand Hotel
Exterior

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.2 out of 10, Wonderful, (1010)
"It’s very close to the local walking mall with stores and nice restaurants. parking was not a problem."
The price is AED 443
AED 502 total
includes taxes & fees
1 Dec - 2 Dec
The George Washington Hotel, A Wyndham Grand Hotel
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.
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Frequently asked questions

Searching for romantic hotels in Old Town Winchester?
Are you looking for a romantic vacation? Our guests also love Old Town Winchester for its array of dining options and interesting historical sites. If you’d like to explore some of the area’s notable sights, you might make a stop by Bright Box Theater, Shenandoah Valley Discovery Museum, or Old Court House Civil War Museum. If you’d like to stay close to a particular destination, you can sort properties by neighborhood or distance to top landmarks, so you’ll be able to see everything on your list.
When is the best time to visit Old Town Winchester?
The hottest months are usually July and August with an average temperature of 72°F,
  • Coldest months: January, February, December, and March
  • Driest months: November, January, February, and March
  • Rainiest months: May, September, June, and July
What is there to do in Old Town Winchester?
There’s nothing better than experiencing a new place with your sweetheart, so consider checking out all that Old Town Winchester has to offer. Couples looking for a little of everything will enjoy Old Town Winchester for its restaurants, bars, and shopping. If you want to spend a day exploring, you might consider a stop at Bright Box Theater, Shenandoah Valley Discovery Museum, or Old Court House Civil War Museum.
What's the best way to get to Old Town Winchester and around town during my romantic getaway?
These transportation options in Old Town Winchester might help your romantic trip go off without a hitch: To get to Old Town Winchester, book a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional), which is the closest major airport, located 18 mi (28.9 km) from the city center. If you’d like to explore around the area, you may want to rent a car for your trip.