Holiday rentals near Winchester Little Theater
We found 287 holiday rentals — enter your dates for availability
Select the perfect holiday rental within easy reach of Winchester Little Theater. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as air conditioning and Wi-Fi. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Winchester Little Theater
Showing deals for:31 Oct - 7 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 AU$2,434
AU$2,434
AU$348 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 AU$2,740
AU$2,740
AU$391 per night
includes taxes & fees
Image gallery for Modern w Mountain Views, Deck & Fire Pit
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Modern w Mountain Views, Deck & Fire Pit
Berkeley Springs, West Virginia
7% off
Price is AU$2,044
AU$2,044
AU$292 per night
includes taxes & fees
Image gallery for River Front Retreat
8.88.8 out of 10 rating
Excellent
(38 reviews)
River Front Retreat
Front Royal, VA
8% off
Price is AU$3,356
AU$3,356
AU$479 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
(9 reviews)
Cozy Chalet, 5-acres, Newly Renovated with WiFi, Deck, Fire Pit & Grill
Gerrardstown, WV
8% off
Price is AU$2,636
AU$2,636
AU$377 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 AU$2,307
AU$2,307
AU$330 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 AU$4,533
AU$4,533
AU$648 per night
includes taxes & fees
Image gallery for Modern 3BR Country Farmhouse
1010 out of 10 rating
Exceptional
(13 reviews)
Modern 3BR Country Farmhouse
Winchester, VA
8% off
Price is AU$3,230
AU$3,230
AU$461 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 AU$2,052
AU$2,052
AU$293 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 AU$2,139
AU$2,139
AU$306 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 AU$5,877
AU$5,877
AU$840 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$4,478
AU$4,478
AU$640 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 AU$1,369
AU$1,369
AU$196 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 AU$2,762
AU$2,762
AU$395 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
24% off
Price is AU$3,087
AU$3,087
AU$441 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 AU$1,884
AU$1,884
AU$269 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 AU$2,862
AU$2,862
AU$409 per night
includes taxes & fees
Image gallery for WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
9.09.0 out of 10 rating
Wonderful
(6 reviews)
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Winchester, VA
16% off
Price is AU$2,366
AU$2,366
AU$338 per night
includes taxes & fees
Image gallery for Timber frame chalet with incredible views minutes from Shenandoah National Park.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Timber frame chalet with incredible views minutes from Shenandoah National Park.
Linden, VA
8% off
Price is AU$6,160
AU$6,160
AU$880 per night
includes taxes & fees
Image gallery for Art Docko - Lakefront Artist Retreat w/ Hot Tub!
1010 out of 10 rating
Exceptional
(19 reviews)
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry, WV
7% off
Price is AU$5,032
AU$5,032
AU$719 per night
includes taxes & fees
Image gallery for Cozy Cabin Hidden Away on a Lake!
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Cozy Cabin Hidden Away on a Lake!
Harpers Ferry, WV
7% off
Price is AU$5,228
AU$5,228
AU$747 per night
includes taxes & fees
Image gallery for Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
1010 out of 10 rating
Exceptional
(45 reviews)
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Star Tannery, VA
12% off
Price is AU$2,537
AU$2,537
AU$362 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 AU$1,577
AU$1,577
AU$225 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
8% off
Price is AU$4,452
AU$4,452
AU$636 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winchester Little Theater
EagleRockCozyCabin hot tub/private/outdoor firepit for friends and family
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Sleeps 7 · 3 bedrooms · 3 bathrooms
8.08.0 out of 10
Very goodvery good
3 reviews(3 reviews)
Shenandoah Retreat near Vineyards/Hiking/River/National Park
Sleeps 8 · 3 bedrooms · 1 bathroom
4.84.8 out of 10
3 reviews(3 reviews)
Breathtaking View with an Indoor Pool
Sleeps 14 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
256 reviews(256 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