Find Casinos in Winchester, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Casinos

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Winchester Casinos

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 AED 200
AED 217 total
includes taxes & fees
1 Jan - 2 January 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, (987)
"Good breakfast, great helpful staff"
United States
Bruce
The price is AED 306
AED 345 total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Martinsburg
Casino
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1011)
"Nice convenient hotel. Clean."
United States
Jason
The price is AED 328
AED 367 total
includes taxes & fees
7 Dec - 8 Dec
Clarion Inn Harpers Ferry - Charles Town
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, (1006)
"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 AED 234
AED 265 total
includes taxes & fees
15 Dec - 16 Dec
Rodeway Inn & Suites - Charles Town, WV
Property grounds
❤️ 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 162
AED 403 total
includes taxes & fees
16 Dec - 17 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
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 AED 441
AED 530 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

Shepherdstown
9.6 out of 10, Exceptional, (39)
"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 936 total
includes taxes & fees
29 Dec - 30 Dec
Charming Cabin in the Woods with River Access
Property grounds
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry
9.6 out of 10, Exceptional, (101)
"The house was beyond expectations."
United States
Eddie J.
The price is AED 408
AED 1,451 total
includes taxes & fees
3 Dec - 4 Dec
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
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 AED 457
AED 516 total
includes taxes & fees
8 Dec - 9 Dec
The Carriage Inn B&B
Property grounds
Best location! The Iron Horse @ historic 1799 Inn

Best location! The Iron Horse @ historic 1799 Inn

Harpers Ferry
9.8 out of 10, Exceptional, (11)
"Perfect location, very nice accommodations! Loved the layout of the top apartment and loved the close proximity to many restaurants and trails. Would love to come back!"
United States
Anna S.
The price is AED 514
AED 949 total
includes taxes & fees
2 Dec - 3 Dec
Best location! The Iron Horse @ historic 1799 Inn
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and friendly!"
Phillip 1-night trip
Posted 11 days ago
The George Washington Hotel, A Wyndham Grand Hotel

Explore a world of travel with Expedia

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.