Holiday rentals near Winchester Little Theater
We found 283 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.
Showing deals for:19 Sept - 26 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 AU$7,366
AU$7,366
AU$1,052 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$4,475
AU$4,475
AU$639 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$4,468
AU$4,468
AU$638 per night
includes taxes & fees
Image gallery for Delicious Cabin | Hot Tub, Screened Porch & More
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Delicious Cabin | Hot Tub, Screened Porch & More
Linden, VA
16% off
Price is AU$3,180
AU$3,180
AU$454 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$4,065
AU$4,065
AU$581 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$3,261
AU$3,261
AU$466 per night
includes taxes & fees
Image gallery for Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
1010 out of 10 rating
Exceptional
(5 reviews)
Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
Paris, VA
8% off
Price is AU$3,720
AU$3,720
AU$531 per night
includes taxes & fees
Image gallery for Still Point Cabin - Harper's Ferry, WV - Mountain Getaway - 3 Bedrooms/AC/WiFi
8.88.8 out of 10 rating
Excellent
(6 reviews)
Still Point Cabin - Harper's Ferry, WV - Mountain Getaway - 3 Bedrooms/AC/WiFi
Bluemont, WV
7% off
Price is AU$2,495
AU$2,495
AU$356 per night
includes taxes & fees
Image gallery for #CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
1010 out of 10 rating
Exceptional
(9 reviews)
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Linden, VA
24% off
Price is AU$2,031
AU$2,031
AU$290 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$3,223
AU$3,223
AU$460 per night
includes taxes & fees
Image gallery for Timber frame chalet with incredible views minutes from Shenandoah National Park.
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Timber frame chalet with incredible views minutes from Shenandoah National Park.
Linden, VA
8% off
Price is AU$6,148
AU$6,148
AU$878 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 AU$2,334
AU$2,334
AU$333 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$2,383
AU$2,383
AU$340 per night
includes taxes & fees
Image gallery for River Perch on the Cacapon: private home on 27 acres and 1200 ft of riverfront
1010 out of 10 rating
Exceptional
(32 reviews)
River Perch on the Cacapon: private home on 27 acres and 1200 ft of riverfront
Yellow Spring, WV
10% off
Price is AU$3,151
AU$3,151
AU$450 per night
includes taxes & fees
Image gallery for Secret Gardens Carriage House
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Secret Gardens Carriage House
Winchester, VA
39% off
Price is AU$1,154
AU$1,154
AU$165 per night
includes taxes & fees
Image gallery for Emerald in Berkeley Springs, WV
1010 out of 10 rating
Exceptional
(28 reviews)
Emerald in Berkeley Springs, WV
Berkeley Springs, WV
12% off
Price is AU$3,329
AU$3,329
AU$476 per night
includes taxes & fees
Image gallery for Blue Mountain Log Cabin
1010 out of 10 rating
Exceptional
(77 reviews)
Blue Mountain Log Cabin
Linden, VA
8% off
Price is AU$2,756
AU$2,756
AU$394 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$2,034
AU$2,034
AU$291 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$2,558
AU$2,558
AU$365 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$1,386
AU$1,386
AU$198 per night
includes taxes & fees
Image gallery for The Overlook
8.88.8 out of 10 rating
Excellent
(8 reviews)
The Overlook
Winchester, VA
7% off
Price is AU$2,331
AU$2,331
AU$333 per night
includes taxes & fees
Image gallery for Newly renovated Farm cottage with Mountain views
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Newly renovated Farm cottage with Mountain views
Strasburg, VA
8% off
Price is AU$2,164
AU$2,164
AU$309 per night
includes taxes & fees
Image gallery for Riverfront Oasis with Mountain Views, close to town
1010 out of 10 rating
Exceptional
(19 reviews)
Riverfront Oasis with Mountain Views, close to town
Middletown, VA
12% off
Price is AU$2,731
AU$2,731
AU$390 per night
includes taxes & fees
Image gallery for Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
1010 out of 10 rating
Exceptional
(11 reviews)
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Winchester, VA
39% off
Price is AU$1,154
AU$1,154
AU$165 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Winchester Little Theater
Showing deals for: 13 Sept - 16 Sept
Modern Country House on the Shenandoah River
Sleeps 8 · 5 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
The current price is AU$1,865
AU$1,865
for 3 nights, 1 home
AU$622 per night
includes taxes & fees
Serene Mountaintop Cabin - Pool, Hot Tub [Fall-Spring], Infrared Sauna
Sleeps 12 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The current price is AU$3,359
AU$3,359
for 3 nights, 1 home
AU$1,120 per night
includes taxes & fees
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
Sleeps 14 · 3 bedrooms · 2+ bathrooms
8.88.8 out of 10
Excellentexcellent
42 reviews(42 reviews)
The current price is AU$3,172
AU$3,172
for 3 nights, 1 home
AU$1,057 per night
includes taxes & fees
Kona's Cozy Cabin — King Bed, Fireplace, Pet Friendly, Near Hiking and Wineries
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is AU$1,110
AU$1,110
for 3 nights, 1 home
AU$370 per night
includes taxes & fees
A-Frame Mountain Retreat
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
The current price is AU$984
AU$984
for 3 nights, 1 home
AU$328 per night
includes taxes & fees
Charming Loft In Winchester Va, Furnished and all Inclusive
Sleeps 2 · 1 bedroom · 1 bathroom
The current price is AU$379
AU$379
for 3 nights, 1 home
AU$126 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