Winchester, VA Vacation Rentals
Check prices for these upcoming dates
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.
The Weather in Winchester
This climate histogram shows you the weather patterns in Winchester. The hottest month in Winchester is June, when temperatures peak at 97 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Winchester is August with 6.12 inches of rain, while the driest month is February with 0.55 inches of rain.
What Expert Travelers Think
— When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place
Whitney WearTravel Better Guide— When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal
KaelinKindly Kae— I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips
Kacie MorganThe Rare Welsh Bit
Vacation Rentals in Winchester
Browse vacation rentals from all your favorite providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. We have 358 vacation rentals, hotels and other places to stay in Winchester ranging from low-cost options to extravagant places to stay. For those traveling on a budget, the cheapest place to stay in Winchester is available at $20 per night. A typical vacation rental in Winchester costs on average $87 a night.
If you want to stay connected during your vacation, then you can choose from over 131 accommodations in Winchester that have WiFi. 13 of our accommodations include a breakfast in the price. You can maintain your workout regime by staying at one of 22 accommodations that provide gym facilities. Driving to Winchester? Then choose one of the 133 places to stay that comes with a parking spot included. 16 hotels and vacation rentals have a a pool or jacuzzi
If you're traveling with a furry friend, then make sure to choose one of the 36 pet-friendly accommodations available.
We aggregate vacation rentals, hotels and other unique accommodation types from loads of providers in Winchester, including 116 places to stay from Airbnb, 22 accommodations from Priceline and 9 places to stay from Agoda
196 of our accommodations in Winchester have been reviewed and rated. 72% are rated excellent or good. 87 places to stay in are instantly bookable.