Find Hotels with Bars in Old Town Winchester, VA

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Check availability on Old Town Winchester Hotels with Bars

Our top choices for Old Town Winchester hotels with a bar

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1013)
"Great hotel!"
United States
CHARLES
The price is NT$3,981
NT$4,511 total
includes taxes & fees
Jan 5 - 2026/1/6
The George Washington Hotel, A Wyndham Grand Hotel

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is NT$3,067
NT$3,383 total
includes taxes & fees
Jan 4 - 2026/1/5
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very Good, (1004)
"Breakfast was delicious "
United States
Robert
The price is NT$2,298
NT$2,557 total
includes taxes & fees
Jan 4 - 2026/1/5
Ramada by Wyndham Strasburg/Shenandoah Valley

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (923)
"comfortable room, amenities and staff"
United States
Prashant
The price is NT$3,363
NT$3,659 total
includes taxes & fees
Jan 5 - 2026/1/6
Courtyard by Marriott Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1002)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is NT$2,452
NT$2,762 total
includes taxes & fees
Jan 18 - 2026/1/19
Holiday Inn Winchester Se-Historic Gateway by IHG

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is NT$7,198
NT$7,940 total
includes taxes & fees
Jan 4 - 2026/1/5
L'Auberge Provencale Inn & Restaurant

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is NT$4,998
NT$6,384 total
includes taxes & fees
Jan 4 - 2026/1/5
Hillbrook Inn

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1001)
"Certainly will stay again "
United States
philip
The price is NT$2,004
NT$2,264 total
includes taxes & fees
Jan 11 - 2026/1/12
Rodeway Inn & Suites Charles Town

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (514)
"Great hotel"
United States
DONNA D
The price is NT$3,171
NT$3,592 total
includes taxes & fees
Jan 5 - 2026/1/6
Hilton Garden Inn Winchester

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
Charles Town
8.6 out of 10, Excellent, (530)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is NT$3,772
NT$4,539 total
includes taxes & fees
Jan 5 - 2026/1/6
The Inn at Charles Town - Hollywood Casino
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.

Top Old Town Winchester Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Old Town Winchester?
Though you might not find a hotel in Old Town Winchester well-known for its bar, you will find 11 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're here, consider a visit to Bright Box Theater and Shenandoah Valley Discovery Museum.
What are the best hotels with bars in Old Town Winchester?
Here are some favorite hotels with bars in and around Old Town Winchester: The George Washington Hotel, A Wyndham Grand Hotel: Hotel with 2 restaurants. Enjoy the bar, free WiFi, and full-service spa. La Quinta Inn & Suites by Wyndham Winchester: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Microtel Inn & Suites by Wyndham Winchester: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Travelodge by Wyndham Winchester: Enjoy the 2 bars, free breakfast, and free WiFi. Days Inn by Wyndham Charles Town/Harpers Ferry: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Old Town Winchester?
To experience the area's highlights, consider visiting Bright Box Theater, Shenandoah Valley Discovery Museum, and Patsy Cline Historic House, and then find a cozy spot for a nightcap. Other places to see include Handley Regional Library and Old Court House Civil War Museum. Old Town Winchester is popular for its top-notch restaurants.
How can I get to Old Town Winchester and around the area?
You might want to make the most of these transportation choices in and around Old Town Winchester: Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) away. You can also search for flights into Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away.

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