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Winchester Accommodations - Hotels & Rentals

About Winchester Vacation Rentals

Discover More than 550 Incredible Getaway Rentals Available in Winchester. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Winchester.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Winchester, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Winchester. The Average Size of Places to Stay Near Winchester is 938.49 ft², with Prices Averaging $342 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Winchester. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Winchester

Type Count
Vacation Homes 214
Holiday Apartments 71
Cottages 20
Villas 19

Use these Quick Filters to Find a Vacation Rental in Winchester

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Winchester with Online Reservations.

Weather in Winchester, VA

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities WinchesterGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World WinchesterGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


SheNonedoah University
Front Royal Entrance SheNonedoah National Park
Winchester Medical Center
Bluemont Vineyard
Skyline Caverns
Dinosaur Land
Apple Blossom Mall
Mt Hebron Cemetery
Jim Barnett Park
SheNonedoah Valley Discovery Museum
Wilson's Wild Animal Park
Patsy Cline Historic House
Twin Oaks Tavern Winery
Blue Ridge Arts Council and Gallery
Bing Crosby Stadium
Watermelon Park Campground
Winchester Little Theater
Holy Cross Abbey
Mackintosh Fruit Farm
Hupp's Hill Civil War Park

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Frederick County 167 Properties
Warren County 160 Properties
Front Royal 149 Properties
Happy Creek 144 Properties
Old Town Winchester 130 Properties
Strasburg 62 Properties
Clarke County 59 Properties
Paris 59 Properties
Berryville 37 Properties
Bluemont 34 Properties
Russell 27 Properties
Stephens City 25 Properties

Frequently Asked Questions About Winchester?

What are the top hotels, lake houses & vacation rentals in Winchester?

We provide an array of great vacation destinations in Winchester. If you are looking to stay in or around the Winchester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winchester:

How many Hotels & Vacation Rentals have private pools in Winchester?

We have 11 Hotels & Vacation Rentals featuring a private pool in and near Winchester. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Winchester is best for families?

Searching for a family-friendly getaway in Winchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winchester?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 550 in the Winchester area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Winchester.


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