Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Find a cheaper way to wander? We'll match it and refund the difference.

Wherever you wander, cancel or rebook most flights within 24 hours without fees.

Need help on your journey? Use our 24/7 social media support @TravelocityHelp.

Most Frequently Booked Winchester Hotels

Country Inn & Suites by Radisson, Winchester, VA $76
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd, Winchester
  • Free Cancellation
  • Reserve now, pay when you stay
 
3.0 out of 5.0

Situated in Winchester, this hotel is within 6 mi (10 km) of The Kernstown Battlefield, Shenandoah University, and Rock Harbor Golf Course. Shenandoah Valley Discovery Museum and Bright Box Theater are also within 6 mi (10 km).

La Quinta Inn & Suites Winchester $89
La Quinta Inn & Suites Winchester

La Quinta Inn & Suites Winchester

1055 Millwood Pike, Route 50 East, Winchester
  • Free Cancellation
  • Reserve now, pay when you stay
 
3.0 out of 5.0

Situated in the suburbs, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom Mall. Abram's Delight and Patsy Cline Historic House are also within 2 mi (3 km).

Travelodge by Wyndham Winchester $49
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester
  • Free Cancellation
  • Reserve now, pay when you stay
 
2.0 out of 5.0

Situated in Winchester, this motel is within 6 mi (10 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Abram's Delight. Apple Blossom Mall and Patsy Cline Historic House are also within 6 mi (10 km).

The George Washington Hotel, A Wyndham Grand Hotel $101
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester
  • Free Cancellation
  • Reserve now, pay when you stay
 
3.5 out of 5.0

Situated in Winchester, this spa hotel is within 6 mi (10 km) of Handley Regional Library, Bright Box Theater, and Old Court House Civil War Museum. Stonewall Jackson's Headquarters and Mt Hebron Cemetery are also within 6 mi (10 km).

Top Cheap Winchester Hotel Deals

Motel 6 Winchester, VA $61
Motel 6 Winchester, VA

Motel 6 Winchester, VA

2951 Valley Avenue, Winchester
  • Free Cancellation
 
2.0 out of 5.0

Located in the heart of Winchester, this motel is 0.6 mi (1 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. Winchester-Frederick County Convention & Visitors Bureau and Shenandoah University are also within 3 mi (5 km).

Travelodge by Wyndham Winchester $49
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester
  • Free Cancellation
  • Reserve now, pay when you stay
 
2.0 out of 5.0

Situated in Winchester, this motel is within 6 mi (10 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Abram's Delight. Apple Blossom Mall and Patsy Cline Historic House are also within 6 mi (10 km).

Twi-Lite Motel $52
Twi-Lite Motel

Twi-Lite Motel

53 West 14th Street, Front Royal
  • Free Cancellation
  • Reserve now, pay when you stay
 
2.0 out of 5.0

Situated in Front Royal, this motel is within 6 mi (10 km) of Bing Crosby Stadium, Belle Boyd Cottage, and Warren Rifles Confederate Museum. Blue Ridge Arts Council and Gallery and Front Royal Visitor's Center are also within 6 mi (10 km).

Royal Inn Motel $50
Royal Inn Motel

Royal Inn Motel

533 S. Royal Avenue, Front Royal
  • Free Cancellation
  • Reserve now, pay when you stay
 
2.5 out of 5.0

Situated in Front Royal, this motel is within a 15-minute walk of Front Royal Entrance Shenandoah National Park, Blue Ridge Arts Council and Gallery, and Front Royal Visitor's Center. Belle Boyd Cottage and Warren Rifles Confederate Museum are also within 15 minutes.

Other Travelers Recently Booked These Winchester Hotels

How Much is a Hotel Room in Winchester?

Hotels in Winchester start at $49 per night. Prices and availability subject to change. Additional terms may apply.

Map

Inspired Winchester Travel Tips

Under The Radar Destination – Middleburg, VA

Travelocity headed to Virginia for this “Under the Radar Destination” column, speaking with Lucy Curtis. Originally from England, Lucy discovered the Virginia Piedmont as a tourist, but today, makes it her home. How did you come to be an expert on Middleburg? I first came to Middleburg as a visitor/tourist, I fell for it so […]

Under The Radar Destination – Middleburg, VA. Opens in a new window.

What are the top landmarks in Winchester?

Don’t miss these must-see sights and attractions


Winchester Hotel & Travel Guide

If you're checking out modern lodgings in Winchester, you'll have no shortage of choices. Right now, Travelocity compares 21 places to stay within a 6-mile (10-kilometer) distance of Winchester's center.

The The George Washington Hotel, A Wyndham Grand Hotel is a much-desired hotel choice thanks to the fact that it is located such a convenient distance from central Winchester.

Stephens City is a district that is where you can find 3 accommodation options, making it the area with the widest range of Winchester hotels. The Holiday Inn & Suites Front Royal Blue Ridge Shadows and Holiday Inn Express Winchester South-Stephens City are great examples of the hotel establishments in and around Stephens City.

Front Royal, Middletown and Strasburg are three alternative Winchester locales that offer excellent lodgings. In Front Royal, accommodation options include the Hampton Inn Front Royal and Cool Harbor Motel. Or, if you base yourself in Middletown, you will be able to pick from the Wayside Inn and Econo Lodge Inn & Suites. Strasburg, which is situated 17 miles (27 kilometers) from the center of town, offers the Fairfield Inn & Suites Strasburg Shenandoah Valley and Hotel Strasburg.

Those traveling on a budget will be happy to know that there is a good range of cheaper places to stay in the vicinity of Winchester. The Comfort Inn Stephens City is 8 miles (12 kilometers) from downtown, while the Ramada Strasburg Va is 16 miles (26 kilometers) away. Other budget room options include the Quality Inn Skyline Dr and the Super 8 Front Royal.

You could also try the Hillbrook Inn along with the The George Washington Hotel, A Wyndham Grand Hotel. The Hillbrook Inn is situated just 13 miles (22 kilometers) away from the city center of Winchester. The The George Washington Hotel, A Wyndham Grand Hotel, is only 0.2 miles (0.3 kilometers) away. Alternative options include the Hampton Inn - Winchester N/Convention Center and the Hilton Garden Inn Winchester.

For those wanting to check out more of the valleys and rolling hills that are a big feature in this region of the country, you should plan some extra time in Shenandoah Valley. Spend your time hiking or discover many of the district's major things to see. Comfortable Travelocity-listed rooms are located nearby.

Woodstock is 30 miles (45 kilometers) to the southwest of Winchester and is home to Woodstock Museum and Shenandoah County Fairgrounds. The Hampton Inn & Suites Woodstock and Holiday Inn Express Woodstock-Shenandoah Valley are some of the Travelocity-listed hotel and apartment options in Woodstock. 45 miles (73 kilometers) southwest of Winchester, you may also choose to stay at New Market, which features the Quality Inn Shenandoah Valley and Days Inn New Market Battlefield. The Endless Caverns and New Market Battlefield are some more popular attractions to check out while in New Market.

Washington Dulles International Airport is a primary gateway for air travel, and is found 40 miles (67 kilometers) away from Winchester's downtown. Travelocity-listed places to stay nearby are Embassy Suites Dulles Airport and Washington Dulles Airport Marriott.


Recent Winchester Hotel Reviews By Fellow Wanderers

Download Our Mobile App

Make booking your next reservation quick & easy. Download the Travelocity mobile app now for even more of the best deals and featured offers. Wander Wisely!