We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Vacation Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Sign in
to get trip updates and message other travelers.
Upperville
Upperville Tourism
Upperville Hotels
Upperville Vacation Rentals
Flights to Upperville
Upperville Restaurants
Things to Do in Upperville
Upperville Travel Forum
Upperville Photos
Upperville Map
Upperville Travel Guide
Hotels
All Upperville Hotels
Upperville Hotel Deals
By Hotel Class
Near Airports
5-stars Hotels in Upperville
4-stars Hotels in Upperville
3-stars Hotels in Upperville
Hotels near (DCA) Ronald Reagan National Airport
Hotels near (IAD) Dulles Intl Airport
Hotels near (BWI) Balt.-Wash. Intl Airport
Things to Do
Restaurants
Flights
Vacation Rentals
Shopping
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Travelers' Choice
Road Trips
Help Center
Travel Stories
Vacation Rentals in Upperville, VA
Vacation Rentals
USA
Virginia (VA)
Vacation Rentals in Upperville, VA
Search
List your property
Owner log in
Upperville
Vacation Rentals
Enter dates
2
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
Air Conditioning (46)
Internet or Wifi (45)
Washer/Dryer (39)
Other outdoor space (35)
Show all
Suitability
Kid friendly (45)
Pet friendly (26)
Elder access (2)
Smoking allowed (2)
Show more
Property type
Vacation Rental House (50)
Condominium/Apartment (0)
Cabin Vacation Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (4)
Boat Available (1)
Private Chef (0)
Private Beach (0)
Show all
Distance from
5 mi
Slater Run Vineyards
Trinity Episcopal Church
Goose Creek Stone Bridge
Show all
50 rentals
in Upperville.
The Mill House in Upperville -
88 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic house in Upperville! Wineries, equestrian events, great location!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
More info
Check in
Check out
Show Prices
The following properties within 20 miles of Upperville match all your filters:
Blue Mountain Log Cabin
62 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
'Anny's Farm House' in Round Hill Wine Country!
55 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Middleburg - Charming Cottage - 5 min to center of M'burg
58 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Virginia Wine Country Retreat 60 mi. from DC
36 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country
26 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
"Best Value": WATERFRONT! 5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester
31 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room
22 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
19 reviews
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
23 reviews
Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
House in Virginia’s Horse and Wine Country
15 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place
14 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic Mountain Cottage at Blue Ridge Overlook
16 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Appalachian Estates Cabin
71 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Peaceful Hideaway w/ Shenandoah River Access
5 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Bedrooms 2, Bathrooms 1, Sleeps 4
8 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historical cottage in the town of Paris
3 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
3 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.
2 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cottage near Middleburg in the Center of Hunt and Wine Country
1 review
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beavers Hill Cottage mountain and wine country getaway
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private entrance Guest suite in Magnificent Manor: stunning views on 150 acres.
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check in
Check out
Show Prices
Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stone Cottage, Comfort, Peace and Nature
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Lovely Guest House 2.5 miles from downtown Middleburg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private, Independent Apartment on Magnificent Manor
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy and secluded cottage located in the heart of horse country.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic Farmhouse Suite in Virginia Hunt & Wine Country
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Whole house near Middleburg in Piedmont horse country
Rental Home
7 bedrooms
7 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautifully Restored Log Cabin in Bluemont, VA
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Modern Home on Middleburg Equestrian Farm
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic Equestrian Estate in Middleburg Hunt Country
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Wine Country Mountain Retreat
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Design home near Middleburg VA available for seasonal stays
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Large Modern House, Wine Country, Delaplane, VA
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
*New* Sampson's Lodge: Mountain Views & Hot Tub
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stunning Bluemont Manor with 8 Bedrooms 7 Baths
Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
18th Century Stone Cottage minutes from historic Middleburg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres
Rental Home
7 bedrooms
7 bathrooms
Sleeps 18
Match:
Sleeps
More info
Check in
Check out
Show Prices
Bluemont Belle is settled on a Historic Equestrian VA Estate
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Hidden View
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historic 1740 log home in the village of Unison, Virginia.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Bright Bluemont Home w/ On-Site Pond & Mtn Views!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
Old Historic Charm on a Lovely 66 acre Farm
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Farm Charm with City Style
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
It's Own Destination / Farm Cottage with Mountain Views & Pond
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
1
Showing results 1-50 of 50
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:
The Mill House in Upperville -
Historic house in Upperville! Wineries, equestrian events, great location!
Middleburg - Charming Cottage - 5 min to center of M'burg
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:
The Mill House in Upperville -
Historic house in Upperville! Wineries, equestrian events, great location!
Middleburg - Charming Cottage - 5 min to center of M'burg
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:
The Mill House in Upperville -
Historic house in Upperville! Wineries, equestrian events, great location!
Middleburg - Charming Cottage - 5 min to center of M'burg
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:
The Mill House in Upperville -
Historic house in Upperville! Wineries, equestrian events, great location!
Appalachian Estates Cabin
See all kid friendly vacation rentals in Upperville on Tripadvisor