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 May, when temperatures peak at 99 ˚F. The coolest month is November, when temperatures drop to 10 ˚F. The wettest month in Winchester is April with 7.5 inches of rain, while the driest month is January with 0.96 inches of rain.
What Expert Travelers Think
— Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.
Samantha WraggCoco Travels— Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options
Sarah PoolTammymum— I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip
Clwyd ProbertWhitehat
Vacation Rentals in Winchester
At AllTheRooms.com we have vacation rentals from all of the leading providers - Airbnb, Priceline, Agoda and others. We have 358 vacation rentals, hotels and other places to stay in Winchester ranging from cheap options to luxury places to stay. If you are wanting to keep costs down, the cheapest place to stay in Winchester is just $20 per night. The average price of an accommodation is around $87 per night.
If you want internet access during your time in Winchester, then you can choose from over 131 places to stay that have WiFi internet. 13 of our accommodations come with breakfast in the price. Choose from 22 places to stay that provide gym facilities, so you won't miss a single workout. 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
Those traveling with a cat, dog or some other animal can stay in any of 36 accommodations that are designated as pet-friendly.
We compare 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 great. 87 places to stay in are instantly bookable.