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Winchester, VA Vacation Rentals

Our Favorite Vacation Rentals in Winchester

See all 410 vacation rentals in Winchester

Winchester Vacation Rentals with Wi-Fi

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Winchester Pet-Friendly Vacation Rentals

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Winchester Travel Guide

In the Shenandoah Valley of northern Virginia lies Winchester. It's a small city that played an important part in the Civil War but nowadays it serves as a small hub for tourism as it's home to leafy green parks, springs, forests, alongside history and museums.

Things to Do in Winchester

To experience the beauty of Winchester, visitors flock to Jim Barnett Park to explore its various trails and enjoy its year-round indoor and outdoor pools. Other great parks in the area include the Frederick Douglass Park and Weaver Park, both of which are ideal for playing soccer and field sports.

Shawnee Springs Preserve, the site of an old Civil War hospital, is the perfect place to admire some of Winchester’s most scenic wetlands, lush forests, and trickling springs.

Meanwhile, history buffs will be amazed by the various historical sites and museums in Winchester, including Stonewall Jackson’s Headquarters, Handley Regional Library, Virginia Museum of Veiled History, Shenandoah Valley Civil War Museum, and the Shenandoah Valley Discovery Museum.

Guests looking to soak in views of the epic Blue Ridge mountain range can make their way to Marker-Miller Orchards to sample tasty cider, donuts, and slushies, and marvel over the countryside views.

Best Places to Stay in Winchester

As for vacation homes, Winchester has a great selection. From log cabins to modern three-story houses, the city has the perfect rental for everyone. Many of the rentals are not only stylish but friendly and spacious, as well, with great views of the surrounding mountains.

Best Time to Visit Winchester

The best time to visit Winchester is from mid-June to July when the sun is shining and the warm weather is at its finest.

Best Events in Winchester

A few of the most exciting things in Winchester are the city's annual events. For example, the St. Paddy's Celtic Fest celebrates everything Celtic, featuring Celtic-themed games, balloon animals, face painting, dancing and music, food vendors, a photo booth, bagpipers, movies, and a petting zoo. Other fun events include the Rockin’ Independence Day Eve, Oktoberfest, and Holly Jolly Celebration.

Things to Do for Families in Winchester

Animal-loving families can spend the day amongst horses at the Rocking S Ranch. The ranch offers guided horseback trail rides with friendly guides that can take riders through streams, forests, fields, and wetlands. They can also feed the animals at Wilson’s Wild Animal Park. Shopping is another great activity, with Winchester offering Apple Blossom Mall and Creekside Station, alongside a dozen other unique shops and local boutiques.

Price and Availability in Winchester

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The most expensive month to stay in a vacation rental in Winchester is in December, while the cheapest month is in March. The most popular time to book a vacation rental in Winchester is in the high season in July. Winchester has its low season in March, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Winchester tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Winchester tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Winchester

90º 41º
8.5
91º 48º
10.46
91º 50º
6.56
90º 52º
4.43
90º 50º
7.24
86º 28º
1.99
73º 21º
5.82
61º 14º
4.28
68º
2.37
81º 10º
3.17
72º 21º
1.82
82º 25º
3.02
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Rainy days
This climate histogram shows you the weather patterns in Winchester. The warmest months in Winchester are June and July, when temperatures reach 91 ˚F. The coolest month is February, when temperatures drop to 10 ˚F. The wettest month in Winchester is June with 10.46 inches of rain, while the driest month is March with 1.82 inches of rain.

What Expert Travelers Think

Vacation Rentals in Winchester

Browse rentals from all your favorite providers including Airbnb, priceline, Agoda and others at AllTheRooms.com. Winchester has 410 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. A vacation in Winchester can be budget-friendly - our lowest price vacation rental is available at $25 a night. The average price of a vacation rental is $93 per night.

If you have to have an internet connection during your stay in Winchester, then you can choose from over 79 accommodations that provide WiFi internet. 21 of our accommodations include a breakfast in the price. Choose from 18 accommodations that provide gym facilities, so you won't miss a single workout. Driving to Winchester? Then choose one of the 85 places to stay that comes with a parking spot included. 13 vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then make sure to select one of the 25 pet-friendly accommodations available.

We aggregate vacation rentals, hotels and other unique accommodation types from loads of providers in Winchester, including 65 places to stay from Airbnb, 19 accommodations from priceline and 9 places to stay from Agoda

179 of the accommodations in Winchester have been reviewed and rated. 70% are rated excellent or good. 56 places to stay in are instantly bookable.