Upperville Vacation Rentals
List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
50 rentals in Upperville.
Sort by:
Tripadvisor Sort
The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Hunt Country Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Large Modern House in Virginia Wine Country
Rental Home
7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Historic Manor House on Shenandoah River in Virginia's Wine Country
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Charming Farmhouse on 36 acres in Shenandoah Wine Country, sleeps 14
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Middleburg, VA - Private Cottage, Sophisticated Country Charm - Newly Remodeled
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Blue Mountain Log Cabin
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Luxurious Chalet, Incredible Views, Stunning Sunsets, Plus Scrapbooking Center
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
English Cottage Five Minutes from Middleburg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Save time - get the best Upperville rentals sent straight to your email!
Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
'Anny's Farm House' in Round Hill Wine Country!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Gorgeous English Hunt Country Cottage
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Riverfront Getaway w/ Breathtaking Views!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Country Cottage on 1700’s Horse Farm/Wedding Venue
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Weekend getaway short distance from DC/Northern Virginia
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Charming Writer's Cottage In The Heart Of Middleburg
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Breathtaking views with an indoor private pool, come escape with us
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Luxury Middleburg Home with 3 Bedrooms and 2 Full Baths
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Virginia Wine Country Retreat 60 mi. from DC
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Quiet Mountain Getaway Minutes from Hiking and Wineries!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
ONE. MINUTE. TO. WINE. 5br #HorseWineBike Home gym, game room, office, fire pit!
Rental Home
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
More info
Check in
Check out
Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Paradise in Horse Country
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Historic Mountain Cottage at Blue Ridge Overlook
Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Cottage w 2 Private Lakes & River Access, Fire Pit
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
The Van Gogh Room in Villa
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Hot Tub Heaven #4 - Vacation Cabin for Rent in Front Royal, Virginia
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Appalachian Estates Cabin
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
'Hot Tub Heaven Cabin #1 - Cabins for Rent in Linden, Virginia
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
'Hot Tub Heaven Cabin #8 - Cabins for Rent in Linden, Virginia
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Hot Tub Heaven #6 - Vacation Cabin for Rent in Linden, Virginia
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Hunt Box on 1700's Horse Farm/Wedding Venue
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
'Hot Tub Heaven Cabin #7 - Cabins for Rent in Linden, Virginia
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Hot Tub Heaven #2 - Vacation Cabins for Rent in Front Royal, Virginia
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
'Hot Tub Heaven #3 - Vacation Cabins for Rent in Linden, Virginia
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
'Hot Tub Heaven #5 - Cabins for Rent in Front Royal, Virginia, United States'
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Hot Tub Heaven #9 - Vacation Cabin for Rent in Linden, Virginia
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Magnificent Manor with stunning views on 150 acres.
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Hi Speed WiFi! Near Middleburg.
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Cottage w 2 Private Lakes & River Access, Fire Pit
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
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
More info
Check in
Check out
Payment Protection
A beautifully restored log cabin in the heart of Virginia hunt & wine country!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Cozy Cabin near Vineyards/Hiking/Shenandoah Parks & River
Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
1
Frequently Asked Questions about Upperville
- 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
- 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
- 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
- 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