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Upperville, VA Holiday Rentals
Holiday Rentals
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Virginia (VA)
Upperville, VA Holiday Rentals
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Air Conditioning (38)
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Kid friendly (30)
Pet friendly (20)
Elder access (1)
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Holiday Rental House (38)
Condominium/Apartment (0)
Cabin Holiday Rental (0)
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Waterfront (3)
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Mountain Views (1)
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38 rentals
in Upperville.
The Mill House in Upperville -
88
Holiday Rental House
4 bedrooms
Sleeps 8
3 bathrooms
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Blue Mountain Log Cabin
62
Holiday Rental House
3 bedrooms
Sleeps 5
2 bathrooms
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'Anny's Farm House' in Round Hill Wine Country!
55
Holiday Rental House
4 bedrooms
Sleeps 8
2 bathrooms
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Middleburg - Charming Cottage - 5 min to center of M'burg
58
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Virginia Wine Country Retreat 60 mi. from DC
36
Holiday Rental House
4 bedrooms
Sleeps 10
4 bathrooms
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Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS
25
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country
26
Holiday Rental House
4 bedrooms
Sleeps 8
4 bathrooms
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"Best Value": WATERFRONT! *5* Star-Rated & VIEWS- Summer Special $199 (SAVE 25%)
31
Holiday Rental House
3 bedrooms
Sleeps 5
2 bathrooms
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One. Minute. To. Wine. Heaven. ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room
22
Holiday Rental House
5 bedrooms
Sleeps 5
4 bathrooms
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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
19
Holiday Rental House
2 bedrooms
Sleeps 6
3 bathrooms
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
23
Holiday Rental House
7 bedrooms
Sleeps 16
8 bathrooms
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House in Virginia’s Horse and Wine Country
15
Holiday Rental House
4 bedrooms
Sleeps 8
3 bathrooms
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1840 7-Acre Farmhouse in VA Wine and Horse Country- Hot Tub, Patio Fire Place
14
Holiday Rental House
5 bedrooms
Sleeps 14
4 bathrooms
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Historic Mountain Cottage at Blue Ridge Overlook
16
Holiday Rental House
3 bedrooms
Sleeps 7
2 bathrooms
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Bedrooms 4, Bathrooms 2, Sleeps 8
26
Holiday Rental House
4 bedrooms
Sleeps 8
2 bathrooms
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Appalachian Estates Cabin
71
Holiday Rental House
3 bedrooms
Sleeps 8
2 bathrooms
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Peaceful Hideaway w/ Shenandoah River Access
5
Holiday Rental House
1 bedroom
Sleeps 7
1 bathroom
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Bedrooms 2, Bathrooms 1, Sleeps 4
8
Holiday Rental House
2 bedrooms
Sleeps 4
1 bathroom
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Historical cottage in the town of Paris!
3
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
3
Holiday Rental House
4 bedrooms
Sleeps 8
2 bathrooms
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Mid-Century Modern Cabin: Mountain & Natural Views
2
Holiday Rental House
2 bedrooms
Sleeps 4
2 bathrooms
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5 Min to Middleburg - Private Guest Suite
2
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Cottage near Middleburg in the Center of Hunt and Wine Country
1
Holiday Rental House
2 bedrooms
Sleeps 4
1 bathroom
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
Holiday Rental House
3 bedrooms
Sleeps 3
3 bathrooms
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Beavers Hill Cottage mountain and wine country getaway
Holiday Rental House
3 bedrooms
Sleeps 6
3 bathrooms
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Private entrance Guest suite in Magnificent Manor: stunning views on 150 acres.
Holiday Rental House
1 bedroom
Sleeps 3
1 bathroom
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NEW Rare 'Cabin in the Clouds' Mountain Getaway w/ Hot Tub City and valley views
Holiday Rental House
2 bedrooms
Sleeps 6
2 bathrooms
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Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive
Holiday Rental House
2 bedrooms
Sleeps 6
2 bathrooms
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Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths
Holiday Rental House
5 bedrooms
Sleeps 11
3 bathrooms
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Whiskey Hill Cabin a mountain getaway in Virginia wine country!
Holiday Rental House
3 bedrooms
Sleeps 4
1 bathroom
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Stone Cottage, Comfort, Peace and Nature
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Lovely Guest House 2.5 miles from downtown Middleburg
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Private, Independent Apartment on Magnificent Manor
Holiday Rental House
1 bedroom
Sleeps 2
2 bathrooms
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Secluded Getaway in Virginia Horse Country Minutes from Middleburg
Holiday Rental House
2 bedrooms
Sleeps 4
2 bathrooms
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Cozy and secluded cottage located in the heart of horse country.
Holiday Rental House
2 bedrooms
Sleeps 4
1 bathroom
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♛Royal A-Frame♛HOT TUB★Treetops★WoodStove★FASTwifi
Holiday Rental House
3 bedrooms
Sleeps 6
1 bathroom
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New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!
Holiday Rental House
5 bedrooms
Sleeps 12
3 bathrooms
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1
Showing results 1-38 of 38
