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Check availability on Winchester Casino Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Winchester Casino Hotels

Lobby
Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA

2.0 star property
Winchester
6.2 out of 10, (619)
"Very limited, bread , butter , jam"
Canada
Susan
The price is 1.434.691 ₫
1.560.944 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Super 8 by Wyndham Winchester VA
Seasonal outdoor pool
Hampton Inn Martinsburg

Hampton Inn Martinsburg

2.5 star property
Martinsburg
8.6 out of 10, Excellent, (992)
"The staff was professional and the rooms were clean"
United States
Sandra
The price is 2.194.234 ₫
2.479.484 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn Martinsburg
Casino
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 star property
Harpers Ferry
8.0 out of 10, Very good, (1012)
"Very nice people in the front desk"
United States
Ximena
The price is 2.353.790 ₫
2.636.244 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Clarion Inn Harpers Ferry - Charles Town
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

3.5 star property
Charles Town
9.6 out of 10, Exceptional, (437)
"Excellent accommodations and breakfast. "
United States
William
The price is 3.417.941 ₫
3.862.274 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Carriage Inn B&B
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, (516)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is 3.164.496 ₫
3.807.997 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
2 bars/lounges, sports bar
Rodeway Inn & Suites - Charles Town, WV

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
Charles Town
8.6 out of 10, Excellent, (1009)
"I loved how clean the hotel was the check-in process was easy and even the people working upfront or super nice."
United States
Paul
The price is 1.681.015 ₫
1.899.547 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Rodeway Inn & Suites - Charles Town, WV
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 casino hotels in Winchester?
If you're heading to Winchester for some gaming, you can roll the dice at Hollywood Casino at Charles Town Races, located 18.5 mi (29.8 km) away, but 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 hotels in Winchester.
When should I take my casino trip to Winchester?
You might spend a lot of your holiday inside, but if you're planning to venture beyond the casino, looking at local weather trends is a good idea. 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.
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, theatres and entertainment venues, and you can visit 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 fly into the nearest airport, which is Martinsburg, WV (MRB-Eastern West Virginia Regional), 18 mi (28.9 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.