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Vacation Rentals in Upperville, VA
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Virginia (VA)
Vacation Rentals in Upperville, VA
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Upperville Vacation Rentals
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Kid friendly (41)
Wheelchair access (6)
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Condominium/Apartment (1)
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Housekeeping Included (6)
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Distance from
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50 rentals
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The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
73 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Hunt Country Cottage
41 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Large Modern House in Virginia Wine Country
1 review
Rental Home
7 bedrooms
4 bathrooms
Sleeps 12
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Historic Manor House on Shenandoah River in Virginia's Wine Country
185 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Charming Farmhouse on 36 acres in Shenandoah Wine Country, sleeps 14
124 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Middleburg, VA - Private Cottage, Sophisticated Country Charm - Newly Remodeled
108 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Blue Mountain Log Cabin
61 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor
51 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Luxurious Chalet, Incredible Views, Stunning Sunsets, Plus Scrapbooking Center
80 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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English Cottage Five Minutes from Middleburg
52 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
63 reviews
Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
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'Anny's Farm House' in Round Hill Wine Country!
53 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous English Hunt Country Cottage
39 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Riverfront Getaway w/ Breathtaking Views!
49 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Country Cottage on 1700’s Horse Farm/Wedding Venue
36 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Weekend getaway short distance from DC/Northern Virginia
57 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Charming Writer's Cottage In The Heart Of Middleburg
75 reviews
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.
49 reviews
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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Breathtaking views with an indoor private pool, come escape with us
148 reviews
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
33 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Luxury Middleburg Home with 3 Bedrooms and 2 Full Baths
23 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Virginia Wine Country Retreat 60 mi. from DC
25 reviews
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
21 reviews
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
23 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Quiet Mountain Getaway Minutes from Hiking and Wineries!
37 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
20 reviews
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!
17 reviews
Rental Home
6 bedrooms
4 bathrooms
Sleeps 18
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
31 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
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Paradise in Horse Country
22 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
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Historic Mountain Cottage at Blue Ridge Overlook
16 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
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Cottage w 2 Private Lakes & River Access, Fire Pit
13 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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The Van Gogh Room in Villa
47 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Hot Tub Heaven #4 - Vacation Cabin for Rent in Front Royal, Virginia
18 reviews
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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Appalachian Estates Cabin
67 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables
5 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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'Hot Tub Heaven Cabin #1 - Cabins for Rent in Linden, Virginia
8 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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'Hot Tub Heaven Cabin #8 - Cabins for Rent in Linden, Virginia
7 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Hot Tub Heaven #6 - Vacation Cabin for Rent in Linden, Virginia
3 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Hunt Box on 1700's Horse Farm/Wedding Venue
2 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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'Hot Tub Heaven Cabin #7 - Cabins for Rent in Linden, Virginia
2 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Hot Tub Heaven #2 - Vacation Cabins for Rent in Front Royal, Virginia
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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'Hot Tub Heaven #3 - Vacation Cabins for Rent in Linden, Virginia
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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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
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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
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Hi Speed WiFi! Near Middleburg.
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
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Cottage w 2 Private Lakes & River Access, Fire Pit
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
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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
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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
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Cozy Cabin near Vineyards/Hiking/Shenandoah Parks & River
Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
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1
Frequently Asked Questions about Upperville
Do any vacation rentals in Upperville have a pool?
Yes, here are some popular vacation rentals in Upperville that have a pool:\n
\n
Hunt Country Cottage
\n
The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
\n
Large Modern House in Virginia Wine Country
\n
\n
See all vacation rentals with a pool in Upperville on Tripadvisor
Do any vacation rentals in Upperville have internet access?
Yes, here are some popular vacation rentals in Upperville that have internet access:\n
\n
Hunt Country Cottage
\n
Large Modern House in Virginia Wine Country
\n
The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
\n
\n
See all vacation rentals in Upperville on Tripadvisor
What are the best pet friendly rentals in Upperville?
The best pet friendly rentals in Upperville are:\n
\n
Hunt Country Cottage
\n
Large Modern House in Virginia Wine Country
\n
The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
\n
\n
See all pet friendly vacation rentals in Upperville on Tripadvisor
What are some great rentals in Upperville that are kid friendly?
Some of the most popular kid friendly rentals in Upperville are:\n
\n
Hunt Country Cottage
\n
The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
\n
Large Modern House in Virginia Wine Country
\n
\n
See all kid friendly vacation rentals in Upperville on Tripadvisor