Book Hotels in Winchester, Virginia

Wander wisely with the Travelocity Price Match Guarantee

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check hotel prices in Winchester

Check prices in Winchester for tonight, Sep 25 - Sep 26
Tomorrow night
Check prices in Winchester for tomorrow night, Sep 26 - Sep 27
Next weekend
Check prices in Winchester for next weekend, Oct 1 - Oct 3

Most frequently booked Winchester hotels

Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Top hotels in Winchester where Kids stay FREE

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.

Top family friendly Winchester hotel deals

Top cheap Winchester hotel deals

Seize your some day

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.

All you need to know about hotels in Winchester 

Where can I find cheap hotels in Winchester?

At Travelocity, you’ll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location—maybe stay at a hotel near Winchester rather than in Winchester—we may find you even better rates, too.

How do I find the best Winchester hotel deals?

Simple! On Travelocity, look through the fantastic offers we’ve already found in Winchester then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Winchester?

The cheapest hotel in Winchester is $60 per night, and we have hotels to suit every budget and every taste. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms may apply.

How many hotels are in Winchester?

There are 157 hotels in Winchester on Travelocity. Out of reviews, the average rating for Winchester hotels is 0.0.

What are the best hotels in Winchester?

Winchester has so many great hotels to choose from at Travelocity—and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!.

When is the best time to visit Winchester?

If you want the joy of a fun-filled trip in peak season, visit Winchester during July, June, May. If you’d prefer the peace of off-season, book a stay during quieter months, such as January, November, December.

When is the cheapest time to stay in Winchester?

Our data shows April is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Winchester?

There are multiple hotels in Winchester that will please the whole family. You need adjoining rooms, baby-sitting services or a swimming pool? We got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kids-friendly hotels in Winchester to choose from on Travelocity!

Why book a hotel in Winchester through Travelocity?

Because we have at the top hotels in Winchester! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Winchester on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers