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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 · Capon Bridge
Secluded Mountain Top Cabin w/hot tub+Pool tbl+Wif
Luxury mountain top cabin offered for you to enjoy nature. Nested on a few acres of land, this property is secluded. Charming double deck overlooking phenomenal views. Relax in the hot tub and take in the views. Eat brunch on the top deck overlooking the endless Mountain Views. Relax on the hammock while reading a book or go to the game room to play pool, table tennis, or the vintage arcade machine. Home is fully equipped with all you need on the kitchen and linens. Ideal to Make memories.
$156 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 Winchester8 locals recommend

Vacation rentals in Winchester

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Entire loft · Winchester
Immerse yourself in Old Town Winchester
$87 per night
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Entire rental unit · Winchester
Downtown Renovated 1920's Gas Station
$130 per night
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Entire rental unit · Winchester
Downtowner
$123 per night
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Entire loft · Winchester
Immerse Yourself in Old Town #3
$70 per night
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Entire rental unit · Winchester
Historic Wisteria House on Old Town Walking Mall
$132 per night
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Entire townhouse · Winchester
Modern Elegance in Historic Old Town Winchester
$120 per night
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Entire rental unit · Winchester
Easy like a Sunday Morning 1 BR apt great location
$73 per night
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Entire cottage · Winchester
Escape to Foxy, Your Private Cottage at Fox Meadow
$212 per night
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Entire rental unit · Winchester
The Loudoun Luxe
$140 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
Old Town Loft In Highly Desirable Area Downtown
$151 per night
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Entire rental unit · Winchester
Rosamond downtown studio apt w/free parking
$101 per night

Weekly rentals in Winchester

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Entire cabin · Augusta ( Capon Bridge)
Nirvana, Mountain View
$65 per night
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Entire cabin · Berkeley Springs
Dreamtime - Modern A-Frame Cabin w/ Hot tub
$292 per night
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Entire cabin · Strasburg
Fall in LOVE@ AVA! Iconic A-frame w/HOT TUB+RIVER!
$218 per night
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Entire cabin · Hedgesville
Bear Pines Retreat ~ Game Room ~ Screened Porch
$235 per night
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Entire cabin · Rileyville
Clouds Cabin
$243 per night
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Entire cabin · Berkeley Springs
Private Creek, Hot Tub, Huge Deck at Chalet Cabin
$249 per night
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Entire cabin · Augusta
Bodhi, Mountain View
$50 per night
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Entire cabin · Luray
Whispering Woods~Renovated~Walk to River~Hot tub
$257 per night
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Entire cabin · Gerrardstown
Wraparound Deck, Fire Pit, WiFi at Chalet Cabin
$75 per night
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Entire cabin · Front Royal
Liberty Hall Cabin - Family Retreat with a View!
$274 per night
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Entire cabin · Augusta
Samadhi Mountain View cabin
$71 per night
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Entire cabin · Charles Town
Vintage Riverfront Log Cabin “Emma” w/hot tub
$188 per night
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