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Upperville Vacation Rentals

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50 rentals in Upperville.
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The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hunt Country Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Large Modern House in Virginia Wine Country

Rental Home
7 bedrooms
4 bathrooms
Sleeps 12
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Historic Manor House on Shenandoah River in Virginia's Wine Country

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Charming Farmhouse on 36 acres in Shenandoah Wine Country, sleeps 14

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Middleburg, VA - Private Cottage, Sophisticated Country Charm - Newly Remodeled

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Blue Mountain Log Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Luxurious Chalet, Incredible Views, Stunning Sunsets, Plus Scrapbooking Center

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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English Cottage Five Minutes from Middleburg

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
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'Anny's Farm House' in Round Hill Wine Country!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous English Hunt Country Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Riverfront Getaway w/ Breathtaking Views!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Country Cottage on 1700’s Horse Farm/Wedding Venue

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Weekend getaway short distance from DC/Northern Virginia

Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Charming Writer's Cottage In The Heart Of Middleburg

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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Breathtaking views with an indoor private pool, come escape with us

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
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Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Luxury Middleburg Home with 3 Bedrooms and 2 Full Baths

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Virginia Wine Country Retreat 60 mi. from DC

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Quiet Mountain Getaway Minutes from Hiking and Wineries!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall

Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
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ONE. MINUTE. TO. WINE. 5br #HorseWineBike Home gym, game room, office, fire pit!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Paradise in Horse Country

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
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Historic Mountain Cottage at Blue Ridge Overlook

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
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Cottage w 2 Private Lakes & River Access, Fire Pit

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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The Van Gogh Room in Villa

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Hot Tub Heaven #4 - Vacation Cabin for Rent in Front Royal, Virginia

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Appalachian Estates Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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'Hot Tub Heaven Cabin #1 - Cabins for Rent in Linden, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'Hot Tub Heaven Cabin #8 - Cabins for Rent in Linden, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hot Tub Heaven #6 - Vacation Cabin for Rent in Linden, Virginia

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hunt Box on 1700's Horse Farm/Wedding Venue

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'Hot Tub Heaven Cabin #7 - Cabins for Rent in Linden, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hot Tub Heaven #2 - Vacation Cabins for Rent in Front Royal, Virginia

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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'Hot Tub Heaven #3 - Vacation Cabins for Rent in Linden, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'Hot Tub Heaven #5 - Cabins for Rent in Front Royal, Virginia, United States'

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hot Tub Heaven #9 - Vacation Cabin for Rent in Linden, Virginia

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Magnificent Manor with stunning views on 150 acres.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Hi Speed WiFi! Near Middleburg.

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cottage w 2 Private Lakes & River Access, Fire Pit

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW Rare 'Cabin in the Clouds' Mountain Getaway w/ Hot Tub City and valley views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A beautifully restored log cabin in the heart of Virginia hunt & wine country!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cabin near Vineyards/Hiking/Shenandoah Parks & River

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
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