Winchester, VA, USA

Winchester, VA, USA

We found 15 vacation rentals — enter your dates for availability

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Find the best place to stay — Winchester

Where to stay around Winchester, VA?

Our 2018 property listings offer a large selection of 15 vacation rentals near Winchester. From 6 houses to 4 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Winchester?

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

  • Shenandoah Valley Discovery Museum: 53 vacation rentals
  • Apple Blossom Mall: 59 vacation rentals
  • Museum of the Shenandoah Valley: 52 vacation rentals
  • Mt Hebron Cemetery: 53 vacation rentals
  • Shenandoah University: 58 vacation rentals

But there are many other points of interest around Winchester listed on HomeAway 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 houses in Winchester?

Yes, of course. HomeAway has 6 houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cottages: 4 rentals available

Can I rent golf rentals in Winchester?

Absolutely, HomeAway has 8 golf rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Mountain rentals: 6 rentals
  • Downtown rentals: 3 rentals
  • Skiing rentals: 3 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 2 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    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.