
House holiday rentals in Winchester
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Top-rated house rentals in Winchester
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester house rentals
House rentals with a pool

Stoney Spring Overlook

Peacefield - Blue Ridge views near Culpeper

Mountain Retreat-Stunning Views/Pool/Hot tub

Spacious & Charming! Large deck+Game shed+Firepit

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

Cedar Creek Wayside Castle

Walnut Lane
Weekly house rentals

Modern~OutdoorCinema~HotTub~EVSE~Games~Dogs

Middleburg/Upperville-Stunning,renovated cottage

Mint Cottage at Little Washington

Valley Vista, stunning views in wine country

XL Spa like tub, giant TVs Best beds EVER Lux desi

Secluded Hilltop Retreat: Log Cabin + Hot Tub

Colonial Era Spring House

Little House on the Prairie in Baker WV
Private house rentals

Day Street - Walk to Harpers Ferry NP

Cabin with Private Waterfront, On River, Fast Wifi

Misty Meadow has quite setting in the country.

Skyview Farmhouse

Cabin in Historic Old Town Winchester

Peaceful Waterfall House is waiting for you.

Highland House

Deer Chase
Quick stats about house rentals in Winchester
Total rentals
40 properties
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
Destinations to explore
- Plainview Holiday rentals
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- Family-friendly rentals Winchester
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- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Gambrill State Park
- Cacapon Resort State Park
- Shenandoah Valley Golf Club
- Robert Trent Jones Golf Club
- Creighton Farms
- Bryce Resort
- South Mountain State Park
- Sly Fox Golf Club
- Whitetail Resort
- Bowling Green Country Club
- River Creek Club
- Berkeley Springs State Park
- Car and Carriage Caravan Museum
- Twin Lakes Golf Course
- Notaviva Vineyards
- Dinosaur Land
- Reston National Golf Course
- JayDee's Family Fun Center
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Warden Lake