Winchester holiday rentals
We found 335 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals close to Winchester, VA (WGO-Winchester Regional) that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Winchester, VA (WGO-Winchester Regional)
Showing deals for:5 Sept - 12 Sept
Image gallery for Whitetail Summit - Shenandoah/hot tub/wineries
1010 out of 10 rating
Exceptional
(39 reviews)
Whitetail Summit - Shenandoah/hot tub/wineries
Front Royal, VA
8% off
Price is AU$7,359
AU$7,359
AU$1,051 per night
includes taxes & fees
Image gallery for Cozy Creekside Cabin with Great Room/Hot Tub
1010 out of 10 rating
Exceptional
(37 reviews)
Cozy Creekside Cabin with Great Room/Hot Tub
Round Hill, VA
8% off
Price is AU$4,895
AU$4,895
AU$699 per night
includes taxes & fees
Image gallery for Luxury Wine Country Escape: Hot Tub & Scenic Views
1010 out of 10 rating
Exceptional
(23 reviews)
Luxury Wine Country Escape: Hot Tub & Scenic Views
Round Hill, VA
20% off
Price is AU$8,745
AU$8,745
AU$1,249 per night
includes taxes & fees
Image gallery for The Mill House in Upperville -
1010 out of 10 rating
Exceptional
(139 reviews)
The Mill House in Upperville -
Upperville, VA
8% off
Price is AU$6,761
AU$6,761
AU$966 per night
includes taxes & fees
Image gallery for Hot Tub Mountain View Dog Friendly Modern Chalet
1010 out of 10 rating
Exceptional
(12 reviews)
Hot Tub Mountain View Dog Friendly Modern Chalet
Linden, VA
7% off
Price is AU$3,845
AU$3,845
AU$549 per night
includes taxes & fees
Image gallery for Mountain Luxury - Hot Tub, Amazing Views & More!
1010 out of 10 rating
Exceptional
(8 reviews)
Mountain Luxury - Hot Tub, Amazing Views & More!
Harpers Ferry, WV
7% off
Price is AU$8,682
AU$8,682
AU$1,240 per night
includes taxes & fees
Image gallery for Waterfront Retreat on the Shenandoah River 7 miles from National Park
1010 out of 10 rating
Exceptional
(18 reviews)
Waterfront Retreat on the Shenandoah River 7 miles from National Park
Front Royal, VA
8% off
Price is AU$4,464
AU$4,464
AU$638 per night
includes taxes & fees
Image gallery for Lamontagne Farmhouse a Rural Pristine Setting
1010 out of 10 rating
Exceptional
(7 reviews)
Lamontagne Farmhouse a Rural Pristine Setting
Bluemont, VA
8% off
Price is AU$3,266
AU$3,266
AU$467 per night
includes taxes & fees
Image gallery for Mt top Cabin/ Hot Tub/ breathtaking views
1010 out of 10 rating
Exceptional
(8 reviews)
Mt top Cabin/ Hot Tub/ breathtaking views
Linden, VA
8% off
Price is AU$2,853
AU$2,853
AU$408 per night
includes taxes & fees
Image gallery for Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
1010 out of 10 rating
Exceptional
(34 reviews)
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Linden, VA
12% off
Price is AU$2,751
AU$2,751
AU$393 per night
includes taxes & fees
Image gallery for Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries
Winchester, VA
8% off
Price is AU$2,083
AU$2,083
AU$298 per night
includes taxes & fees
Image gallery for Modern 3BR Country Farmhouse
1010 out of 10 rating
Exceptional
(10 reviews)
Modern 3BR Country Farmhouse
Winchester, VA
8% off
Price is AU$3,220
AU$3,220
AU$460 per night
includes taxes & fees
Image gallery for Secluded, Cozy Cottage in the Shenandoah Valley
1010 out of 10 rating
Exceptional
(174 reviews)
Secluded, Cozy Cottage in the Shenandoah Valley
Maurertown, VA
8% off
Price is AU$2,931
AU$2,931
AU$419 per night
includes taxes & fees
Image gallery for New Hot Tub! Next to resort with spa and golf!
1010 out of 10 rating
Exceptional
(5 reviews)
New Hot Tub! Next to resort with spa and golf!
Capon Springs, WV
8% off
Price is AU$3,258
AU$3,258
AU$465 per night
includes taxes & fees
Image gallery for Serene Mountaintop Cabin - Pool, Hot Tub [Fall-Spring], Infrared Sauna
1010 out of 10 rating
Exceptional
(51 reviews)
Serene Mountaintop Cabin - Pool, Hot Tub [Fall-Spring], Infrared Sauna
Gore, VA
8% off
Price is AU$5,782
AU$5,782
AU$826 per night
includes taxes & fees
Image gallery for Luxury Lodge Fire Pit, Hot Tub, & Sauna
1010 out of 10 rating
Exceptional
(23 reviews)
Luxury Lodge Fire Pit, Hot Tub, & Sauna
Front Royal, VA
16% off
Price is AU$5,106
AU$5,106
AU$729 per night
includes taxes & fees
Image gallery for Delicious Cabin | Hot Tub, Screened Porch & More
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Delicious Cabin | Hot Tub, Screened Porch & More
Linden, VA
16% off
Price is AU$2,726
AU$2,726
AU$389 per night
includes taxes & fees
Image gallery for Romantic, family friendly mountain getaway w hot tub near wineries & skyline
1010 out of 10 rating
Exceptional
(16 reviews)
Romantic, family friendly mountain getaway w hot tub near wineries & skyline
Front Royal, VA
12% off
Price is AU$3,989
AU$3,989
AU$570 per night
includes taxes & fees
Image gallery for WV Cozy Cabin Summit Point Races
9.89.8 out of 10 rating
Exceptional
(24 reviews)
WV Cozy Cabin Summit Point Races
Kearneysville, WV
8% off
Price is AU$1,630
AU$1,630
AU$233 per night
includes taxes & fees
Image gallery for Mountain View Cottage @ 66-acre Horse Farm
8.48.4 out of 10 rating
Very good
(8 reviews)
Mountain View Cottage @ 66-acre Horse Farm
Berryville, VA
8% off
Price is AU$3,841
AU$3,841
AU$549 per night
includes taxes & fees
Image gallery for #CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
1010 out of 10 rating
Exceptional
(8 reviews)
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Linden, VA
24% off
Price is AU$2,008
AU$2,008
AU$287 per night
includes taxes & fees
Image gallery for Cozy Chalet, 5-acres, Newly Renovated with WiFi, Deck, Fire Pit & Grill
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Cozy Chalet, 5-acres, Newly Renovated with WiFi, Deck, Fire Pit & Grill
Gerrardstown, WV
8% off
Price is AU$2,540
AU$2,540
AU$363 per night
includes taxes & fees
Image gallery for Beavers Hill Cottage a Mountain getaway in Virginia Wine country! W/hot tub
9.89.8 out of 10 rating
Exceptional
(273 reviews)
Beavers Hill Cottage a Mountain getaway in Virginia Wine country! W/hot tub
Front Royal, VA
8% off
Price is AU$2,541
AU$2,541
AU$363 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winchester
Charming Loft In Winchester Va, Furnished and all Inclusive
Sleeps 2 · 1 bedroom · 1 bathroom
Lake View Retreat - Cottage Near a Peaceful Lake!
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Cedarbank • Cabin in Virginia Wine Country
Sleeps 4 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Pet-Friendly Berryville Home: Walk to Main Street!
Sleeps 4 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
The Shenandoah Basset Dacha
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value