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
  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Casino Hotels

This weekend
Next weekend

Our top choices for Winchester hotels with a casino

Super 8 by Wyndham Winchester VA

Super 8 by Wyndham Winchester VA
2.0 star property
Winchester
6.2 out of 10, (645 reviews)
"It smelled of cigarettes in the hallway and vestibule. The sink in our room did not drain well. The continental breakfast was terrible. Juice machine was out of order. To eat was only cereal and toast. The breakfast room did not look very nice."
United States
Gayle Robin
The price is €60
includes taxes & fees
7 Jul - 8 Jul
Super 8 by Wyndham Winchester VA

4BR Golf Retreat | 3 Courses | Pool Table

4BR Golf Retreat | 3 Courses | Pool Table
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is €563
includes taxes & fees
20 Jul - 21 Jul
4BR Golf Retreat | 3 Courses | Pool Table

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1,001 reviews)
"Wonderful place to stay"
United States
Jeremiah
The price is €71
includes taxes & fees
2 Aug - 3 Aug
Rodeway Inn & Suites Charles Town

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,002 reviews)
"Great location and nice comfy room. Staff very friendly and helpful. Solid breakfast."
United States
Dan
The price is €101
includes taxes & fees
3 Aug - 4 Aug
Clarion Inn Harpers Ferry - Charles Town

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (79 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is €129
includes taxes & fees
4 Aug - 5 Aug
❤️ Secluded 1940s Romantic Tiny House on the River

Hampton Inn Martinsburg

Hampton Inn Martinsburg
2.5 star property
Martinsburg
8.8 out of 10, Excellent, (1,002 reviews)
"Great property, great stay"
United States
Jameika
The price is €96
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn Martinsburg

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, (590 reviews)
"Property was clean and staff was helpful."
United States
Lee
The price is €123
includes taxes & fees
7 Jul - 8 Jul
The Inn at Charles Town - Hollywood Casino

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (82 reviews)
"The cabin was amazing, very rustic, it had everything that we could need to be comfortable, the shooting range was a great extra feature, we will definitely return."
United States
Patricia R.
The price is €294
includes taxes & fees
8 Jul - 9 Jul
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (451 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is €166
includes taxes & fees
7 Jul - 8 Jul
The Carriage Inn B&B

Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors
Harpers Ferry
9.4 out of 10, Exceptional, (85 reviews)
"We enjoyed this house very comfy cozy we stayed because we had a celebration of life and me and my family were able to just unwind here thank u so much we loved it and the jacuzzi was wonderful "
United States
Jennifer B.
The price is €323
includes taxes & fees
9 Jul - 10 Jul
Rural Home, Hot Tub, Campfire, Hardwood Floors
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.

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 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 Winchester Little Theater and Museum of the Shenandoah Valley. 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