Winchester holiday homes
We found 340 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:7 Nov - 14 Nov
Image gallery for Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Gerrardstown, West Virginia
7% off
Price is NZ$3,306
NZ$3,306
NZ$472 per night
includes taxes & fees
Image gallery for Amazing Views, Hot Tub, Fire Pit, Deck & Fireplace
9.29.2 out of 10 rating
Wonderful
(35 reviews)
Amazing Views, Hot Tub, Fire Pit, Deck & Fireplace
Gerrardstown, West Virginia
7% off
Price is NZ$3,807
NZ$3,807
NZ$544 per night
includes taxes & fees
Image gallery for Private Cabin Retreat | Hot Tub, Game Room, & More
1010 out of 10 rating
Exceptional
(9 reviews)
Private Cabin Retreat | Hot Tub, Game Room, & More
Front Royal, VA
12% off
Price is NZ$8,025
NZ$8,025
NZ$1,146 per night
includes taxes & fees
Image gallery for Modern Chalet w Hot Tub, Large Deck, Grill & WiFi
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern Chalet w Hot Tub, Large Deck, Grill & WiFi
Gerrardstown, West Virginia
7% off
Price is NZ$2,792
NZ$2,792
NZ$399 per night
includes taxes & fees
Image gallery for River Front Retreat
8.88.8 out of 10 rating
Excellent
(39 reviews)
River Front Retreat
Front Royal, VA
8% off
Price is NZ$3,685
NZ$3,685
NZ$526 per night
includes taxes & fees
Image gallery for Luxury Wine Country Escape: Hot Tub & Scenic Views
1010 out of 10 rating
Exceptional
(25 reviews)
Luxury Wine Country Escape: Hot Tub & Scenic Views
Round Hill, VA
20% off
Price is NZ$12,997
NZ$12,997
NZ$1,857 per night
includes taxes & fees
Image gallery for Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.49.4 out of 10 rating
Exceptional
(59 reviews)
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Harpers Ferry, West Virginia
8% off
Price is NZ$5,923
NZ$5,923
NZ$846 per night
includes taxes & fees
Image gallery for Hot Tub, Private Creek Access, High Speed Internet, Romantic vibes
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Hot Tub, Private Creek Access, High Speed Internet, Romantic vibes
Gerrardstown, WV
7% off
Price is NZ$1,501
NZ$1,501
NZ$214 per night
includes taxes & fees
Image gallery for The Overlook
9.09.0 out of 10 rating
Wonderful
(10 reviews)
The Overlook
Winchester, VA
8% off
Price is NZ$2,535
NZ$2,535
NZ$362 per night
includes taxes & fees
Image gallery for On the river ~ hot tub ~ serene river views ~ fire pit
1010 out of 10 rating
Exceptional
(19 reviews)
On the river ~ hot tub ~ serene river views ~ fire pit
Strasburg, VA
8% off
Price is NZ$5,822
NZ$5,822
NZ$832 per night
includes taxes & fees
Image gallery for Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
1010 out of 10 rating
Exceptional
(16 reviews)
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Bluemont, VA
8% off
Price is NZ$5,482
NZ$5,482
NZ$783 per night
includes taxes & fees
Image gallery for Newly renovated Farm cottage with Mountain views
1010 out of 10 rating
Exceptional
(32 reviews)
Newly renovated Farm cottage with Mountain views
Strasburg, VA
8% off
Price is NZ$2,351
NZ$2,351
NZ$336 per night
includes taxes & fees
Image gallery for Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive
Front Royal, VA
8% off
Price is NZ$4,679
NZ$4,679
NZ$668 per night
includes taxes & fees
Image gallery for Luxury Lodge Fire Pit, Hot Tub, & Sauna
1010 out of 10 rating
Exceptional
(24 reviews)
Luxury Lodge Fire Pit, Hot Tub, & Sauna
Front Royal, VA
17% off
Price is NZ$6,835
NZ$6,835
NZ$976 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$4,913
NZ$4,913
NZ$702 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown
Middletown, VA
11% off
Price is NZ$1,759
NZ$1,759
NZ$251 per night
includes taxes & fees
Image gallery for Mt top Cabin/ Hot Tub/ breathtaking views
1010 out of 10 rating
Exceptional
(10 reviews)
Mt top Cabin/ Hot Tub/ breathtaking views
Linden, VA
8% off
Price is NZ$3,144
NZ$3,144
NZ$449 per night
includes taxes & fees
Image gallery for The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
8.88.8 out of 10 rating
Excellent
(42 reviews)
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
Berryville, VA
8% off
Price is NZ$6,409
NZ$6,409
NZ$916 per night
includes taxes & fees
Image gallery for Secluded, Cozy Cottage in the Shenandoah Valley
1010 out of 10 rating
Exceptional
(180 reviews)
Secluded, Cozy Cottage in the Shenandoah Valley
Maurertown, VA
8% off
Price is NZ$3,230
NZ$3,230
NZ$461 per night
includes taxes & fees
Image gallery for Spacious Historical Manor
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Spacious Historical Manor
Strasburg, VA
7% off
Price is NZ$2,103
NZ$2,103
NZ$300 per night
includes taxes & fees
Image gallery for Mountain cabin near national park & wineries
1010 out of 10 rating
Exceptional
(26 reviews)
Mountain cabin near national park & wineries
Linden, VA
25% off
Price is NZ$4,467
NZ$4,467
NZ$638 per night
includes taxes & fees
Image gallery for Secluded River Cabin Getaway (Masten Cabin)
9.89.8 out of 10 rating
Exceptional
(157 reviews)
Secluded River Cabin Getaway (Masten Cabin)
Strasburg, VA
8% off
Price is NZ$1,510
NZ$1,510
NZ$216 per night
includes taxes & fees
Image gallery for Blue Mountain Log Cabin
1010 out of 10 rating
Exceptional
(78 reviews)
Blue Mountain Log Cabin
Linden, VA
8% off
Price is NZ$3,034
NZ$3,034
NZ$433 per night
includes taxes & fees
Image gallery for Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
9.09.0 out of 10 rating
Wonderful
(25 reviews)
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
Front Royal, Virginia
7% off
Price is NZ$2,793
NZ$2,793
NZ$399 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Winchester
Showing deals for: 2 Nov - 5 Nov
Cute cabin retreat near Shenandoah National Park and pet friendly!
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is NZ$1,498
NZ$1,498
for 3 nights, 1 cabin
NZ$499 per night
includes taxes & fees
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Sleeps 6 · 3 bedrooms · 2 bathrooms
7.67.6 out of 10
Goodgood
8 reviews(8 reviews)
The current price is NZ$1,385
NZ$1,385
for 3 nights, 1 cabin
NZ$462 per night
includes taxes & fees
Hot Tub Chalet-Fire Pit, Grill, Stream & Big Yard
Sleeps 10 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
The current price is NZ$944
NZ$944
for 3 nights, 1 cabin
NZ$315 per night
includes taxes & fees
Linden Family Home w/ Yard < 5 Mi to Wineries!
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
12 reviews(12 reviews)
The current price is NZ$1,857
NZ$1,857
for 3 nights, 1 home
NZ$619 per night
includes taxes & fees
Lake View Retreat - Cottage Near a Peaceful Lake!
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
The current price is NZ$1,332
NZ$1,332
for 3 nights, 1 cottage
NZ$444 per night
includes taxes & fees
Nature Escape | Pond, Dock, Fire Pit, Trails
Sleeps 12 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$2,718
NZ$2,718
for 3 nights, 1 home
NZ$906 per night
includes taxes & fees
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