Find Casinos in Winchester, VA

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Check availability on Winchester Casinos

Our top choices for Winchester hotels with a casino

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Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (620)
"Very limited, bread , butter , jam"
Canada
Susan
The price is AED 239
AED 260 total
includes taxes & fees
1 Jan - 2 January 2026
Super 8 by Wyndham Winchester VA
Seasonal outdoor pool
Hampton Inn Martinsburg

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.6 out of 10, Excellent, (1002)
"Front desk was very considerate and friendly. Hotel was very clean. "
United States
Barry
The price is AED 306
AED 345 total
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn Martinsburg
Casino
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1001)
"Very nice people in the front desk"
United States
Ximena
The price is AED 328
AED 367 total
includes taxes & fees
21 Dec - 22 Dec
Clarion Inn Harpers Ferry - Charles Town
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 AED 234
AED 265 total
includes taxes & fees
28 Dec - 29 Dec
Rodeway Inn & Suites Charles Town
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (65)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is AED 149
AED 388 total
includes taxes & fees
17 Dec - 18 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
Casino
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, (520)
"the room was clean and the staff was great. The shuttle service to the casino was awesome."
United States
Steve
The price is AED 477
AED 571 total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Exterior
Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (40)
"My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. "
United States
Leana H.
The price is AED 459
AED 924 total
includes taxes & fees
29 Dec - 30 Dec
Charming Cabin in the Woods with River Access
Smart TV
Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (11)
"Great location in Lower Harper's Ferry. We completely enjoyed our stay. Will definitely be staying again in the future."
United States
Andrew R.
The price is AED 477
AED 810 total
includes taxes & fees
18 Dec - 19 Dec
Best location! Baltimore Suite @ historic 1799 Inn
Terrace/patio
Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (67)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is AED 585
AED 1,235 total
includes taxes & fees
15 Dec - 16 Dec
Cottage on King | Charming Historic Leesburg Home
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 462
AED 522 total
includes taxes & fees
15 Dec - 16 Dec
The Carriage Inn B&B
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Great hotel!"
CHARLES 1-night trip
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel
Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Front desk was very considerate and friendly. Hotel was very clean. "
Barry 1-night trip
Posted 5 days ago
Hampton Inn Martinsburg

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Frequently asked questions

Searching for casino hotels in Winchester?
If you're planning a gaming trip to Winchester, you can roll the dice at Hollywood Casino at Charles Town Races, located 18.5 mi (29.8 km) away, though it's not the only place to visit while you're in town. Tourists speak highly of the historic landmarks, shopping, and local cuisine.
How many hotels that are good for gaming will I find in Winchester?
Get your game on at one of Expedia's 79 lodging options close to the casinos in Winchester.
When should I take my casino trip to Winchester?
You might spend a lot of your vacation inside, but if you want to see more of the area, looking at local weather trends is a good idea. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What is there to do in Winchester?
You can head to Apple Blossom Mall, Apple Valley Square Shopping Center, or Northpark Shopping Center to shop for the perfect souvenir. Winchester is known for its historic sites, theaters, and entertainment venues, and you can check out cultural spots such as Museum of the Shenandoah Valley and Old Court House Civil War Museum. In addition, you might want to visit Bright Box Theater and Shenandoah Valley Discovery Museum.
What are my transportation options for my casino getaway to Winchester?
Here are some transportation options in Winchester: You can arrange a flight to the nearest airport, which is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.