Discover a selection of 279 vacation rentals in Winchester, VA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $41 per night, and cabins and houses are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winchester
Destination guide

Welcome to the Apple Capital

The sheer number of orchards that dot the landscape around Winchester have earned it the nickname the "Apple Capital". Just moments from Winchester vacation rentals, in the historic downtown district, you'll find dozens of restaurants and cafes to choose from, as well as dozens of retails shops to keep even the pickiest of shoppers happy. Alternatively, head out to the Old Town Pedestrian Mall which hosts live music all year round. It's perhaps most famous for the annual Shenandoah Apple Blossom Festival which attracts more than a quarter of a million folks over the event in spring.

Things to do

A wealth of history to discover

There's a surprising number of attractions in Winchester, many of which focus on the fascinating history of the town and county. Just down the road from Winchester vacation rentals, you can visit Abram's Delight Museum, one of the largest and oldest 18th-century log cabins. Alternatively, history buffs will be interested by George Washington's Office Museum or the Museum of the Shenandoah Valley which houses art and cultural artifacts in an old property. Be sure to visit the Patsy Cline Historic House which offers a glimpse into the life of this country music legend.


Hike, gallop and bike

Regardless of what you're into, Winchester has you covered. From your Winchester vacation rental, you can pack up your clubs for a morning on the championship-style golf course, go hiking and biking along the Shenandoah Valley or saddle up to gallop through along the shady trails that meander up through the foothills and ridges. Alternatively, head out into the wilderness for a night under the stars or watch a homerun at a baseball game. You won't be far from peaceful riverside locations where you can cast your line in to hook a trout or salmon.


Summer is busiest, but not always the best

Winchester enjoys distinct seasonal variation – sometimes in the same day. If you want to visit during late spring or summer when the weather is at its best and the skies are bright and clear, you'll need to book your Winchester vacation rental early. Don't let that stop you from visiting in the other seasons through. With fewer people to contend with on the biking and horseback riding trails and the forests alive with bright fall colors, September to November can be a wonderfully peaceful time to visit. Winter is often cold and snowy, but that brings a whole wealth of other adventurous activities.

Natural features

Watch the wildlife in Shenandoah

Just a short drive from your Winchester vacation rental is the Shenandoah National Park, a must-see for wildlife lovers with so many resident animals to spot. With such an abundance of species, a visit to the park rarely fails to deliver sights of white-tailed deer herds, solitary bobcats or scampering gray squirrels. We don't recommend you get too close, but it's not uncommon to see the odd black bear wander through the forest or even an elusive coyote. As darkness creeps in, so do the big brown bats and spotted skunks.

How to get there

How to get to and around Winchester

The nearest airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Washington, DC (IAD-Washington Dulles Intl.), which is 41.7 mi (67.1 km) away.

How many vacation rentals are available around Winchester, VA?

Our 2021 property listings offer a large selection of 279 vacation rentals around Winchester. From 69 cabin rentals to 223 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Winchester?

Vrbo offers a large selection of vacation rentals near lovely places in Winchester. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Rocking S Ranch: 107 vacation rentals
  • Patsy Cline Historic House: 86 vacation rentals
  • Museum of the Shenandoah Valley: 76 vacation rentals
  • Shenandoah University: 92 vacation rentals
  • Apple Blossom Mall: 88 vacation rentals

But there are many other points of interest around Winchester listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cabins in Winchester?

Yes, of course. Vrbo has 69 Cabins in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Houses: 223 rentals available
  • Cottages: 63 rentals available
  • Condos/Apartments: 17 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 39 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.