Find Casinos in Old Town Winchester, VA

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Check availability on Old Town Winchester Casinos

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Old Town Winchester Casinos

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)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is SAR 450
SAR 542 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, (1002)
"Good for me and front desk allowed me to check in early"
United States
Devan
The price is SAR 239
SAR 270 total
includes taxes & fees
21 Dec - 22 Dec
Rodeway Inn & Suites - Charles Town, WV
Courtyard
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 SAR 477
SAR 539 total
includes taxes & fees
30 Dec - 31 Dec
The Carriage Inn B&B
Fridge, microwave, oven, stovetop
The River House

The River House

Charles Town
10.0 out of 10, Exceptional, (10)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is SAR 365
SAR 999 total
includes taxes & fees
9 Dec - 10 Dec
The River House
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 SAR 244
SAR 265 total
includes taxes & fees
1 Jan - 2 January 2026
Super 8 by Wyndham Winchester VA
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

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 13 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

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Frequently asked questions

Searching for casino hotels in Old Town Winchester?
Tourists speak highly of the historic landmarks and local cuisine.
How many hotels that are good for gaming should I expect to find in Old Town Winchester?
Win big at one of Expedia's 12 lodging options close to the casinos in Old Town Winchester.
What is there to do in Old Town Winchester?
You can head to Apple Blossom Mall, Apple Valley Square Shopping Center, or Northside Station Shopping Center to shop for the perfect souvenir. Old Town Winchester is known for its historic sites and live music, and you can check out cultural spots such as Old Court House Civil War Museum, Museum of the Shenandoah Valley, and Winchester Little Theater. Additionally, you might want to add Bright Box Theater and Shenandoah Valley Discovery Museum to your itinerary.