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Our top choices for Upperville apartments

1. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine CountryMarkham
9.6 out of 10, Exceptional, (5 reviews)
$261 nightly
The price is $280
Nov 9 - Nov 10
Total with taxes and fees

2. Lunar Loft, with mountain views
Lunar Loft, with mountain viewsBluemont
9.4 out of 10, Exceptional, (13 reviews)
$226 nightly
The price is $258
Nov 9 - Nov 10
Total with taxes and fees

3. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.Bluemont
9.8 out of 10, Exceptional, (15 reviews)
$285 nightly
The price is $324
Nov 10 - Nov 11
Total with taxes and fees

4. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.Middleburg
9.6 out of 10, Exceptional, (29 reviews)
$226 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees

5. Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Romantic African-Inspired Studio on Alpaca Farm – Under the StarsThe Plains
10.0 out of 10, Exceptional, (12 reviews)
$452 nightly
The price is $485
Nov 8 - Nov 9
Total with taxes and fees

6. Downtown Apt 3 • 2BR • Near Park & River • Private
Downtown Apt 3 • 2BR • Near Park & River • PrivateFront Royal
10.0 out of 10, Exceptional, (1 review)
$249 nightly
The price is $274
Nov 12 - Nov 13
Total with taxes and fees

7. Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main StreetWarrenton
10.0 out of 10, Exceptional, (13 reviews)
$232 nightly
The price is $254
Nov 15 - Nov 16
Total with taxes and fees

8. The Queen of Winchester Three Bedroom with Upper Level Deck
The Queen of Winchester Three Bedroom with Upper Level DeckWinchester
7.6 out of 10, Good, (8 reviews)
$218 nightly
The price is $225
Nov 8 - Nov 9
Total with taxes and fees

9. Cozy 1BR Apt Minutes From Skyline Drive!!
Cozy 1BR Apt Minutes From Skyline Drive!!Amissville
9.6 out of 10, Exceptional, (48 reviews)
$208 nightly
The price is $219
Nov 7 - Nov 8
Total with taxes and fees

10. Rosamond nice downtown studio apt
Rosamond nice downtown studio aptWinchester Historic District
8.8 out of 10, Excellent, (3 reviews)
$162 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees

11. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
$219 nightly
The price is $248
Nov 19 - Nov 20
Total with taxes and fees

12. Historic 2-Bedroom in Old Town Warrenton, Virginia
Historic 2-Bedroom in Old Town Warrenton, VirginiaWarrenton
10.0 out of 10, Exceptional, (85 reviews)
$251 nightly
The price is $274
Nov 8 - Nov 9
Total with taxes and fees

13. Morocco Loft 2BR overlooking city walking mall
Morocco Loft 2BR overlooking city walking mallOld Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
$273 nightly
The price is $309
Nov 15 - Nov 16
Total with taxes and fees

14. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mallWinchester Historic District
8.4 out of 10, Very good, (6 reviews)
$197 nightly
The price is $223
Nov 15 - Nov 16
Total with taxes and fees

15. The Stock Exchange downtown 3rd floor studio apt
The Stock Exchange downtown 3rd floor studio aptWinchester Historic District
7.0 out of 10, Good, (2 reviews)
$167 nightly
The price is $189
Nov 12 - Nov 13
Total with taxes and fees

16. Downtown Apt 2 • 2BR • Near Park & River • Private
Downtown Apt 2 • 2BR • Near Park & River • PrivateFront Royal
$267 nightly
The price is $292
Nov 10 - Nov 11
Total with taxes and fees

17. Nostalgia Lane in the heart of the city
Nostalgia Lane in the heart of the cityOld Town Winchester
8.8 out of 10, Excellent, (21 reviews)
$270 nightly
The price is $306
Nov 8 - Nov 9
Total with taxes and fees

18. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Downtown Apt.1 • 2BR/2BA• Near Park/River• PrivateFront Royal
10.0 out of 10, Exceptional, (1 review)
$269 nightly
The price is $295
Nov 12 - Nov 13
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Upperville
Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.






























































































































