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Winchester cabins

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Top-rated cabins in Winchester

Guests agree: these cabins are highly rated for location, cleanliness, and more.

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Entire cabin · Winchester
Majestic Mountain Cabin
Spectacular 100 mile panoramic view from the top of Big Bear Mountain. This well appointed cabin has an open floor plan with an updated kitchen and breakfast bar with seating for four. Living room has comfortable furnishings and a wood burning fireplace with raised hearth. Two spacious bedrooms and custom bathroom. Watch the sunrise and sunset over Shenandoah Valley from the wrap around deck. Comfortable outdoor furniture for relaxing. Close to wineries and historic downtown Winchester.
$150 per night
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Entire cabin · Strasburg
Strasburg Cabin Hideaway!
New Listing-just renovated **4/2022 Peaceful cabin getaway. Pet friendly, grill and hot tub! Approximately 12 minutes from the town of Strasburg, antique capital of Virginia. Hallmark-esque town, quiet and peaceful, great retreat if you’re looking to get away from the city or hiking in the Shenandoah’s. Close to Woodbine Farms And the best coffee at Nancy’s coffee shop. Rain shower, high tech water filtration system. Relax and grill out, play games, etc.
$160 per night
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Entire cabin · Strasburg
Cedar River Retreat~ River Access~Hot Tub~King Bed
Gorgeous log cabin nestled in the forest with lovely river access within the community. Soak in serenity, visit nearby wineries, go antiquing and of course canoe, kayak, or float down the river, or simply sit on the bank and listen to the water rush by. Walk through our wooded lot and you will see deer, squirrels, and Willy, our resident grandaddy groundhog (he loves apples if you want to bring him a treat.)
$188 per night

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Stay near Winchester's top sights

Photo of Museum of the Shenandoah Valley
Museum of the Shenandoah Valley30 locals recommend
Photo of Shenandoah Valley Discovery Museum
Shenandoah Valley Discovery Museum18 locals recommend
Photo of Brightbox Theater
Brightbox Theater11 locals recommend
Photo of Handley Regional Library
Handley Regional Library3 locals recommend
Photo of Patsy Cline Historic House
Patsy Cline Historic House4 locals recommend
Photo of Old Town Winchester
Old Town Winchester9 locals recommend

Vacation rentals in Winchester

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Entire loft · Winchester
Immerse yourself in Old Town Winchester
$79 per night
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Entire rental unit · Winchester
Downtowner
$123 per night
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Entire rental unit · Winchester
The New Yorker Quiet tucked away 1BR walk to town
$112 per night
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Entire rental unit · Winchester
Downtown Renovated 1920's Gas Station
$120 per night
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Private room · Winchester
Hot tub, private bedroom and bath. Huge great room
$55 per night
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Entire rental unit · Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
$128 per night
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Entire rental unit · Winchester
Rosamond downtown studio apt w/free parking
$101 per night
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Entire rental unit · Winchester
Pretty Little Apt by the Train II
$113 per night
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Entire rental unit · Winchester
The Blue Door steps from Handley Library
$116 per night
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Entire loft · Winchester
Immerse Yourself in Old Town #3
$76 per night
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Entire townhouse · Winchester
Modern Elegance in Historic Old Town Winchester
$123 per night
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Entire rental unit · Winchester
Historic Wisteria House on Old Town Walking Mall
$134 per night

Weekly rentals in Winchester

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Entire cabin · Strasburg
Fall in LOVE@ AVA! Iconic A-frame w/HOT TUB+RIVER!
$200 per night
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Entire cabin · Winchester
Cheerful 2 bedroom cabin with a hot tub
$200 per night
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Entire cabin · Berkeley Springs
Wood Cabin W/WiFi + hot tub + Fire Pit + Pool tbl
$113 per night
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Entire cabin · Berkeley Springs
Modern Cabin: Hot Tub, FirePit, Pond, & Wood Stove
$111 per night
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Entire cabin · Berkeley Springs
Horizon Hill - Log Cabin w/Hot Tub & Views!
$213 per night
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Entire cabin · Charles Town
Vintage Riverfront Log Cabin “Emma” w/hot tub
$191 per night
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Entire cabin · Front Royal
Welcome to Skyhouse! A Modern Riverfront Retreat
$290 per night
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Entire cabin · Harpers Ferry
Applemoon: Charming Log Cabin in a Mountain Lake Community
$186 per night
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Entire cabin · Front Royal
NEW Romantic “Cabin in the Clouds” getaway w H/Tub
$335 per night
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Entire cabin · Gerrardstown
Wraparound Deck, Fire Pit, WiFi at Chalet Cabin
$139 per night
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Entire cabin · Front Royal
Treehouse, Your Riverside Nirvana Experience!
$286 per night
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Entire cabin · Berkeley Springs
Modern Cabin w Hot Tub, Pond, Deck, Fire Pit, WiFi
$144 per night
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