Search Casino Hotels in Old Town Winchester

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Check availability on Old Town Winchester Casino Hotels

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

Top Old Town Winchester Casino Hotels

Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

3.5 star property
Charles Town
9.6 out of 10, Exceptional, (438)
"Excellent accommodations and breakfast. "
United States
William
The price is 3.417.682 ₫
3.861.981 ₫ 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 3.164.256 ₫
3.807.708 ₫ 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, (1010)
"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 1.680.888 ₫
1.899.402 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Rodeway Inn & Suites - Charles Town, WV
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 1.434.582 ₫
1.560.825 ₫ total
includes taxes & fees
4 Jan - 5 Jan 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

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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 are there in Old Town Winchester?
Get your game on at one of Expedia's 12 accommodation options 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 visit 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.