Search Hotels with a Bar in Old Town Winchester

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Check availability on Old Town Winchester Hotels with a Bar

Our top choices for Old Town Winchester hotels with a bar

Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

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, (1007)
"Great hotel!"
United States
CHARLES
The price is ฿4,030
฿4,566 total
includes taxes & fees
17 Dec - 18 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1001)
"Friendly Staff, clean room."
Canada
Frank
The price is ฿2,272
฿2,529 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

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, (1001)
"Todo excelente "
Mexico
Anner Javier
The price is ฿2,355
฿2,658 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ฿3,114
฿3,530 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (914)
"comfortable room, amenities and staff"
United States
Prashant
The price is ฿3,405
฿3,705 total
includes taxes & fees
17 Dec - 18 Dec
Courtyard by Marriott Winchester
Front of property
Hillbrook Inn

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 ฿5,060
฿6,463 total
includes taxes & fees
11 Dec - 12 Dec
Hillbrook Inn
Restaurant
The Inn at Charles Town - Hollywood Casino

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, (521)
"the room was clean and the staff was great. The shuttle service to the casino was awesome."
United States
Steve
The price is ฿4,137
฿4,951 total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Interior
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (508)
"Great hotel"
United States
DONNA D
The price is ฿3,038
฿3,443 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Winchester
2 bars/lounges, sports bar
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1003)
"Good for me and front desk allowed me to check in early"
United States
Devan
The price is ฿2,028
฿2,292 total
includes taxes & fees
28 Dec - 29 Dec
Rodeway Inn & Suites Charles Town
Garden
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (174)
"Wonderful staff and service!"
United States
Eliel Constantine
The price is ฿9,515
฿10,495 total
includes taxes & fees
11 Dec - 12 Dec
L'Auberge Provencale Inn & Restaurant
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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Top Old Town Winchester Hotel Reviews

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Nice, clean, quiet rooms. Staff were polite and professional. I would stay here again. "
JAMES 2-night trip
Posted 3 weeks ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Frequently asked questions

Searching for hotels with bars in Old Town Winchester?
Though you might not find a hotel in Old Town Winchester that's well known for its bar, you will find 12 properties to choose from, some of which will have an on-site 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 a few of the top 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. Travelodge 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 breakfast and free WiFi. Comfort Inn & Suites Winchester: Hotel with restaurant. Enjoy the bar, free WiFi and free parking.
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 cosy spot for a nightcap. Other places to see include Old Court House Civil War Museum and Handley Regional Library. 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. Otherwise, you can search for flights to Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away.