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Featured Vacation Homes in Winchester

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The Outpost: a Rustic Respite in the Shenandoah Valley - 4 Tesla Bikes For Use

The Outpost: a Rustic Respite in the Shenandoah Valley - 4 Tesla Bikes For Use

Berryville, VA
Situated in Berryville, this historic vacation home is within 1 mi (2 km) of The Fire House Gallery and Barns of Rose Hill. Veramar Vineyard and Mackintosh Fruit Farm are also within 6 mi (10 km).
 
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Celebration Retreat

Celebration Retreat

5.0 out of 5.0 440 Scenic Overlook Dr, Front Royal, VA
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. You'll appreciate the area shuttle, terrace, and garden.
 
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The Nest in Chester Gap

The Nest in Chester Gap

Front Royal, VA
A spa tub is featured at this vacation home, along with barbecue grills.
 
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Quiet Mountain Getaway Minutes From Hiking and Wineries!

Quiet Mountain Getaway Minutes From Hiking and Wineries!

Bluemont, VA
Situated in Bluemont, this vacation home is within 9 mi (15 km) of Veramar Vineyard, Holy Cross Abbey, and Bluemont Vineyard. The Fire House Gallery and Barns of Rose Hill are also within 9 mi (15 km).
 
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" Zen Garden Art Studio" Tiny Home With a Loft ~and Stairs ~ Queen Size Bed

" Zen Garden Art Studio" Tiny Home With a Loft ~and Stairs ~ Queen Size Bed

Winchester, VA
This vacation home includes a garden and laundry facilities.
 
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Shenandoah Stone House With Kayaks & Self Check-in

Shenandoah Stone House With Kayaks & Self Check-in

Bluemont, VA
This vacation home features barbecue grills.
 
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Breathtaking Views With an Indoor Private Pool, Come Escape With us

Breathtaking Views With an Indoor Private Pool, Come Escape With us

Bluemont, VA
This vacation home features an indoor pool and a fitness center. Enjoy the spa tub and conveniences like a garden and concierge services.
 
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Exquisite Riverfront Paradise...100+ Acres- Hike, Boat, Swim Without Leaving!

Exquisite Riverfront Paradise...100+ Acres- Hike, Boat, Swim Without Leaving!

Front Royal, VA
A fitness center is featured at this vacation home, along with a terrace and a garden.
 
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Ashby s Gap Retreat in Historic Paris, VA

Ashby s Gap Retreat in Historic Paris, VA

Paris, VA
A garden is available at this vacation home.
 
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Great Views, Hike Onsite, Work Remotely, Huge Smart TVs & Hot-tub

Great Views, Hike Onsite, Work Remotely, Huge Smart TVs & Hot-tub

Strasburg, VA
A spa tub is featured at this vacation home, along with a garden.
 
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Colonial Getaway Near Old Town Historic Winchester

Colonial Getaway Near Old Town Historic Winchester

Winchester, VA
Situated in Winchester, this vacation home is within 3 mi (5 km) of Mt Hebron Cemetery, Jim Barnett Park, and Old Court House Civil War Museum. Handley Regional Library and Bright Box Theater are also within 3 mi (5 km).
 
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City Charmer Near Historic Oldtown Winchester

City Charmer Near Historic Oldtown Winchester

Winchester, VA
A garden is available at this vacation home.
 
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Winchester Vacation Home Rentals

What kind of vacation do you want in Winchester? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation home is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Winchester that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Winchester, including luxury vacation home rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rental houses close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation homes a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.


Top trending hotels in Winchester

See all 108 Properties in Winchester
$104
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5.0 118 Mercedes Court, Winchester, VA
Situated in Winchester, this hotel is within 6 mi (10 km) of Stonewall Jackson's Headquarters, Handley Regional Library, and Old Court House Civil War Museum. Bright Box Theater and Mt Hebron Cemetery are also within 6 mi (10 km).
 
$84
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3.0 out of 5.0 141 Kernstown Commons Blvd, Winchester, VA
Situated in Winchester, this hotel is 2.2 mi (3.5 km) from The Kernstown Battlefield and within 6 mi (10 km) of Shenandoah University and Rock Harbor Golf Course. Shenandoah Valley Discovery Museum and Bright Box Theater are also within 6 mi (10 km).
 
$98
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5.0 103 E Piccadilly St, Winchester, VA
Located in the heart of Winchester, this spa hotel is within a 10-minute walk of Handley Regional Library and Shenandoah Valley Discovery Museum. Winchester Little Theater and Patsy Cline Historic House are also within 15 minutes.
 
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.