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Check availability on Winchester Hotels with a Bar

Our top choices for Winchester hotels with a bar

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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, (1005)
"Breakfast was delicious "
United States
Robert
The price is 1.900.681 ₫
2.115.459 ₫ total
includes taxes & fees
21 Dec - 22 Dec
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, (1004)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is 1.841.490 ₫
2.082.462 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Restaurant
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (915)
"comfortable room, amenities and staff"
United States
Prashant
The price is 2.814.849 ₫
3.062.555 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Winchester
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1010)
"Great hotel!"
United States
CHARLES
The price is 3.331.782 ₫
3.774.908 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The George Washington Hotel, A Wyndham Grand Hotel
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, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is 2.567.037 ₫
2.831.440 ₫ total
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (509)
"Great hotel"
United States
DONNA D
The price is 2.511.792 ₫
2.845.861 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Winchester
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (94)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is 8.128.863 ₫
8.884.926 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Glen Gordon Manor
Terrace/patio
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)
"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 7.865.793 ₫
8.675.970 ₫ total
includes taxes & fees
16 Dec - 17 Dec
L'Auberge Provencale Inn & Restaurant
Property entrance
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (916)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is 1.453.462 ₫
1.617.703 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
Breakfast area
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is 1.633.665 ₫
1.801.934 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Econo Lodge Inn & Suites Middletown - Winchester South
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 Winchester Hotel Reviews

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Frequently asked questions

Searching for hotels with bars in Winchester?
If you prefer a place to stay where you can enjoy an evening cocktail after sightseeing, Winchester features 79 properties, including 5 accommodation options with an on-site bar. While you're here, consider a visit to Bright Box Theater and Shenandoah Valley Discovery Museum.
How many hotels with bars on site will I find in Winchester?
Expedia has 5 hotels with a bar in Winchester.
What is there to do in Winchester?
Consider a visit to 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 Museum of the Shenandoah Valley and Apple Blossom Mall. Winchester is popular for its array of shops and top-notch restaurants.
When is the best time to visit Winchester?
Visiting local bars in Winchester is more fun when you know what the weather holds. These rainfall averages and temperatures can help you choose the best time for bar-hopping. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
How can I get to Winchester and around the area?
Here are some of your transportation options in and around Winchester: Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. Otherwise, look for flights into Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.