Winchester Hotel Guide - Casino Hotels in Winchester, Virginia

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Top Winchester Casino Hotels

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 €54
includes taxes & fees
15 Dec - 16 Dec
Super 8 by Wyndham Winchester VA

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Boyce
10.0 out of 10, Exceptional, (31)
"Good location. Large fenced in yard. Plenty of room. Would book again."
United States
Don M.
The price is €472
includes taxes & fees
24 Nov - 25 Nov
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Hampton Inn Martinsburg

2.5 star property
Martinsburg
8.6 out of 10, Excellent, (971)
"Good breakfast, great helpful staff"
United States
Bruce
The price is €82
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Martinsburg

Clarion Inn Harpers Ferry - Charles Town

2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1007)
"Nice convenient hotel. Clean."
United States
Jason
The price is €87
includes taxes & fees
2 Dec - 3 Dec
Clarion Inn Harpers Ferry - Charles Town

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
Charles Town
8.6 out of 10, Excellent, (1004)
"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 €62
includes taxes & fees
7 Dec - 8 Dec
Rodeway Inn & Suites - Charles Town, WV

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is €95
includes taxes & fees
1 Dec - 2 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

The Inn at Charles Town - Hollywood Casino

3.0 star property
Charles Town
8.6 out of 10, Excellent, (514)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is €252
includes taxes & fees
20 Dec - 21 Dec
The Inn at Charles Town - Hollywood Casino

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 €127
includes taxes & fees
24 Nov - 25 Nov
The Carriage Inn B&B

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 €226
includes taxes & fees
4 Dec - 5 Dec
Charming Cabin in the Woods with River Access

Hot tub, Campfire ring and great location!

Harpers Ferry
9.4 out of 10, Exceptional, (125)
"We had an amazing time in WV. The home was comfortable and met all of our needs. It was quiet and relaxing, but close to the major attractions for the action."
United States
Katrina P.
The price is €353
includes taxes & fees
24 Nov - 25 Nov
Hot tub, Campfire ring and great location!
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

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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, Winchester Gateway or Apple Valley Square 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.