Winchester, VA Hotels & Vacation Rentals

Discover unbelievably low rates on Winchester hotels and great deals on a wide ranging inventory of unique vacation rentals - 26 great properties to choose from! Free TravNow Membership can save you an additional 20% or more off our already low prices, join today and save!
Why Book With TravNow? Why TravNow?

Become a Free TravNow Member & Save More Today!    Sign Up Now & Start Saving!

Save 20%+ on

Hotels & Vacation Rentals

Members Save 20% or More

Off Our Already Low Public Prices!

Save Hundreds on

Condo & Timeshare Rentals

Your TravNow Bookings Benefit Charity

5% of our commission on every TravNow booking is donated to charity. TravNow Bookings Benefit Charity Learn More

Become a Member Today - Free!

Sign Up Now For Free Free Member Signup
  • Save Big On Hotels & Vacation Rentals
    Save Big On Hotels, Condos, and Vacation Rentals

    Our publicly-available rates are among the lowest on the internet, but sign up for a free TravNow membership and get immediate access to our hidden "members-only" rates that can save you 20% or more on top of our low everyday rates.

  • Access To Non-Public "Travel Agent" Pricing & Inventory

    We are able to offer our private members access to wholesale pricing that the hotels and huge travel websites don't want the public to see!

  • Unique Vacation Inventory
    Unique Vacation Inventory

    Our members have access to interesting and unique vacation inventory like heavily discounted vacation condos and timeshare rentals that can't be found on other "hotel-only" travel sites - our members can save hundreds or even thousands of dollars booking these special deals.

  • TravNow Member Rewards
    Member Rewards Program

    Members are automatically enrolled in the internet's top reward program - stay 12 nights, and earn one night FREE! It's easy to earn valuable rewards while saving with TravNow!

Discover The Lowest Prices Available On The World's Top Hotel Brands
Book The World's Top Hotel Brands With TravNow
Winchester VA hotels
hotels in Winchester
Winchester hotels & vacation rentals

Where To Stay In Winchester, Virginia

Located in the heart of the picturesque Shenandoah Valley, Winchester, Virginia is a charming and historic city that attracts tourists from all over the world. Surrounded by scenic mountains and rolling countryside, Winchester offers visitors a unique blend of natural beauty, rich history, and modern amenities. With its convenient location just a short drive from major cities like Washington D.C. and Baltimore, it's no wonder that Winchester is a popular destination for travelers seeking a peaceful and relaxing getaway. Whether you're a history buff, outdoor enthusiast, or simply looking for a cozy, small-town experience, Winchester has something for everyone.

One of the main draws to Winchester for tourists is its fascinating historical attractions. The city was a major hub during the Civil War, and visitors can explore its rich past at the Winchester National Cemetery, Stonewall Jackson's Headquarters, and the Kernstown Battlefield. Winchester's charming Old Town district also offers quaint shops, delicious restaurants, and historic buildings dating back to the 1700s. Other must-see neighborhoods include the charming Loudoun Street Mall, bustling Winchester Marketplace, and scenic Berryville Avenue. For accommodations, tourists can choose from a variety of Winchester hotels, ranging from luxurious resorts to cozy bed and breakfasts.

In addition to its historical and cultural offerings, Winchester also boasts numerous outdoor activities and events. The city is home to several parks and trails, including the breathtaking Shenandoah National Park, where visitors can hike, bike, and camp amidst stunning scenery. The annual Shenandoah Apple Blossom Festival draws crowds to Winchester every spring, while the Virginia Hot Glass Festival and Patsy Cline Music Festival are also popular events. For those interested in wine tasting, the Shenandoah Valley Wine Trail has over 20 vineyards and wineries to explore. With so many things to do in Winchester, there's always something new and exciting to discover.

In conclusion, Winchester, Virginia is a charming and diverse city that offers tourists an unforgettable experience. From its rich history and quaint neighborhoods to its outdoor activities and events, there's something for everyone to enjoy in this beautiful destination. Plus, with a variety of hotels in Winchester to choose from, visitors can find the perfect accommodation for their stay. So pack your bags and come experience all that Winchester has to offer!

Winchester Travel Guide

Featured Winchester Tourism Information Articles
Tourism Information Articles
Exploring Winchester's Rich History

A Stroll Through Old Town
Winchester, Virginia may be a small city, but it is steeped in rich history and charm. As a local, one of the best ways to experience this history is t...

Read Article
Tourism Information Articles
Class of Hotels

There are a variety of accommodation options to choose from when visiting Winchester, VA. For those who prefer the traditional hotel experience, there are several chain hotels, such as Hilton, Holi...

Read Article
Local Restaurant Spotlight
Local Restaurant Spotlight: Our "Top Restaurant Choice For Travelers - 2023"

 The Village Square Restaurant

Read Our Review
Featured Hotels & Vacation Rentals
Featured Hotels & Vacation Rentals in Winchester

TravNow is pleased to feature the following Winchester hotels & vacation rentals which were rated highest overall in our guest reviews:

View All Featured Winchester Hotels & Vacation Rentals
Return To Top