Find Casinos in Winchester, VA

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Our top choices for Winchester hotels with a casino

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (621)
"Very limited, bread , butter , jam"
Canada
Susan
The price is NT$2,111
NT$2,297 total
includes taxes & fees
Dec 29 - Dec 30
Super 8 by Wyndham Winchester VA

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.6 out of 10, Excellent, (1017)
"Great hotel in a good location near stores, restaurants, etc! "
United States
Mawrin V
The price is NT$2,687
NT$3,036 total
includes taxes & fees
Jan 1 - 2026/1/2
Hampton Inn Martinsburg

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1004)
"Rooms were clean, staffs were friendly and the breakfast was good."
United States
Mouleeswaran
The price is NT$2,812
NT$3,149 total
includes taxes & fees
Jan 1 - 2026/1/2
Clarion Inn Harpers Ferry - 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)
"Certainly will stay again "
United States
philip
The price is NT$2,008
NT$2,269 total
includes taxes & fees
Jan 11 - 2026/1/12
Rodeway Inn & Suites Charles Town

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, (526)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is NT$3,781
NT$4,549 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.

Find out more about Winchester

Discover top Winchester attractions

For travelers with a penchant for casinos, Winchester, Virginia, offers a unique blend of historical charm and gaming excitement just a short drive away. Head to the nearby West Virginia for a thrilling day trip to the Hollywood Casino at Charles Town Races, where you can enjoy a wide array of slot machines and table games, all while soaking in the electrifying atmosphere of live horse racing. Back in Winchester, explore the vibrant Old Town area, where you can find the charming Loudoun Street Mall filled with boutique shops and delightful eateries, perfect for a relaxing stroll after a day of gaming. Don't miss the Museum of the Shenandoah Valley, which offers engaging exhibits and beautiful gardens, providing a serene contrast to the high-energy casino experience. For those interested in a bit of local history, the Patsy Cline Historic House is a must-visit, celebrating the legacy of the beloved singer. When it comes to accommodations, the downtown area features upscale hotels like the George Washington Hotel, where quality service meets modern amenities, ensuring a pampered stay. After a day of adventure and gaming, unwind in style as you enjoy the local dining scene and take in the historic ambiance that Winchester has to offer.

Top Winchester Hotel Reviews

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 78 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 Winchester Little Theater. 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.

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