Winchester holiday homes
We found 333 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
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Whitetail Summit - Shenandoah/hot tub/wineries
Front Royal, VA
8% off
Price is NZ$8,108
NZ$8,108
NZ$1,158 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 NZ$5,287
NZ$5,287
NZ$755 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 NZ$9,611
NZ$9,611
NZ$1,373 per night
includes taxes & fees
Image gallery for The Mill House in Upperville -
1010 out of 10 rating
Exceptional
(140 reviews)
The Mill House in Upperville -
Upperville, VA
8% off
Price is NZ$7,454
NZ$7,454
NZ$1,065 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 NZ$4,091
NZ$4,091
NZ$584 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 NZ$9,386
NZ$9,386
NZ$1,341 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 NZ$4,823
NZ$4,823
NZ$689 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 NZ$3,529
NZ$3,529
NZ$504 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 NZ$3,085
NZ$3,085
NZ$441 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 NZ$2,975
NZ$2,975
NZ$425 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 NZ$2,222
NZ$2,222
NZ$317 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 NZ$3,490
NZ$3,490
NZ$499 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 NZ$3,169
NZ$3,169
NZ$453 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 NZ$3,522
NZ$3,522
NZ$503 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 NZ$2,969
NZ$2,969
NZ$424 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 NZ$5,512
NZ$5,512
NZ$787 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 NZ$4,291
NZ$4,291
NZ$613 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 NZ$6,235
NZ$6,235
NZ$891 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 NZ$1,763
NZ$1,763
NZ$252 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 NZ$2,165
NZ$2,165
NZ$309 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 NZ$2,757
NZ$2,757
NZ$394 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
(274 reviews)
Beavers Hill Cottage a Mountain getaway in Virginia Wine country! W/hot tub
Front Royal, VA
8% off
Price is NZ$2,714
NZ$2,714
NZ$388 per night
includes taxes & fees
Image gallery for Whitetail Cabin | Couple's Retreat w/ Hot Tub
1010 out of 10 rating
Exceptional
(18 reviews)
Whitetail Cabin | Couple's Retreat w/ Hot Tub
Linden, VA
11% off
Price is NZ$2,193
NZ$2,193
NZ$313 per night
includes taxes & fees
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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