A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Hotel Guide - Casino Hotels in Winchester, Virginia

  • 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 Casino Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Winchester hotels with a casino

1. Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
Winchester
United States
Naomi
€58
includes taxes & fees
1 Nov - 2 Nov
Super 8 by Wyndham Winchester VA

2. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
United States
Felice N.
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

3. Golfers' Paradise: 3 Courses Nearby + Pool Table

Golfers' Paradise: 3 Courses Nearby + Pool Table
Front Royal
United States
Crystal H.
€497
includes taxes & fees
12 Oct - 13 Oct
Golfers' Paradise: 3 Courses Nearby + Pool Table

4. The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
Charles Town
United States
Kira
€119
includes taxes & fees
7 Oct - 8 Oct
The Inn at Charles Town - Hollywood Casino

5. Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
Charles Town
United States
Biju
€64
includes taxes & fees
1 Nov - 2 Nov
Rodeway Inn & Suites Charles Town

6. Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
Charles Town
United States
Catherine
€71
includes taxes & fees
7 Oct - 8 Oct
Days Inn by Wyndham Charles Town/Harpers Ferry

7. Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG
Charles Town
United States
Rhonda
€91
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express Charles Town by IHG

8. Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
Harpers Ferry
United States
Jean
€91
includes taxes & fees
1 Nov - 2 Nov
Clarion Inn Harpers Ferry - Charles Town

9. Hampton Inn Martinsburg

Hampton Inn Martinsburg
Martinsburg
United States
Matthew
€84
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Martinsburg

10. Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town
Charles Town
United States
Scott
€126
includes taxes & fees
12 Oct - 13 Oct
Home2 Suites by Hilton Charles Town
View all properties

Find out more about Winchester

Discover top Winchester attractions

While Winchester, Virginia may not boast casinos, it offers an array of attractions that can appeal to travellers seeking a thrilling experience. For history enthusiasts, the Museum of the Shenandoah Valley can captivate with its extensive collection of American art and history, making it a perfect day trip to soak in the local culture. Outdoor adventurers can explore the scenic trails of the nearby Shenandoah National Park, where you can hike and enjoy breathtaking views, adding a touch of excitement to your stay. For a unique evening out, the vibrant downtown area features several local breweries and restaurants, where you can indulge in craft beers and delicious cuisine while soaking in the local atmosphere. The historic Old Town is dotted with charming shops, offering an eclectic mix of antiques and artisanal goods, perfect for a leisurely afternoon stroll. Finally, for those seeking a more adrenaline-fuelled experience, the nearby Shenandoah Speedway hosts various racing events, providing a thrilling experience just a short drive away. When it comes to accommodation, the hotels in and around Old Town Winchester offer a blend of comfort and charm, allowing you to unwind after a day of exploring. Many establishments pride themselves on exceptional service, ensuring your stay is pampered and relaxed, with convenient access to all the local attractions.

Top Winchester Hotel Reviews

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 75 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.

Explore a world of travel with Expedia