Where to stay around Winchester, VA?

Our 2018 property listings offer a large selection of 220 vacation rentals near Winchester. From 75 Bungalows to 75 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 VRBO.

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:

  • Museum of the Shenandoah Valley: 62 vacation rentals
  • Shenandoah Valley Discovery Museum: 66 vacation rentals
  • Apple Blossom Mall: 72 vacation rentals
  • Stonewall Jackson's Headquarters: 66 vacation rentals
  • Winchester-Frederick County Convention & Visitors Bureau: 70 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 Bungalows in Winchester?

Yes, of course. VRBO has 75 Bungalows in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cottages: 75 rentals available
  • Cabins: 75 rentals available
  • Houses: 66 rentals available

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your prefered vacation rental with pool among our 54 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.

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