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Price range

Per night

$10 - $500

Rental types

Upperville Rentals

23 Houses

Large Modern House, VA Wine Country

Upperville house

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$199

1 / 31

Great rentals within 20 miles that match your search

Monet Suite, elegnt lrg 2rm suite/blcny in villa

Purcellville house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$200

1 / 31

Beautiful & Spacious Detached Home

Leesburg house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 27 minutes

Price per night from

$229

1 / 21

'Anny's Farm House' in Round Hill Wine Country!

Round Hill house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 10 minutes

Price per night from

$285

1 / 24

Rainbow View Cabin - Shenandoah Valley view & hottub

Linden log cabin

2 bedrooms / 1 bathroom / sleeps 4

“Perfect as always” Lovely anniversary weekend. Owners are amazing which makes the already well maintained and perfectly located property seem even better... Already checking my calendar for next trip!

Responds fast! avg. 13 minutes

Price per night from

$150

1 / 45

Franklin Manor - Close to Front Royal and Attractions

Front Royal house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$200

1 / 28

Charming Historic Home in Shenandoah Valley Wine Country near Skyline Drive

Winchester house

5 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 40 minutes

Price per night from

$250

1 / 72

Wine Country Retreat 60 miles from DC

Markham house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 42 minutes

Price per night from

$498

1 / 5

Turquoise room at Loudoun Valley Manor - near Leesburg off Route 9

Waterford house

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 37 minutes

Price per night from

$85

1 / 28

Sienna Room at Loudoun Valley Manor - off Route 9 near Leesburg

Waterford b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 37 minutes

Price per night from

$75

1 / 25

Golden Room at Loudoun Valley Manor near Leesburg

Waterford house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 37 minutes

Price per night from

$95

1 / 29

Green room - suite at Loudoun Valley Manor

Waterford house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 37 minutes

Price per night from

$105

1 / 25

Just Like Heaven Carriage House

Winchester cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$125

1 / 24

Celebration Retreat, a fun venue in Wine Country

Front Royal house

4 bedrooms / 5 bathrooms / sleeps 25

“Very lovely and full of entertainment!!” Me and my girlfriend had wonderful time at this home. Especially, the theater was great and view from home was fantastic.

Price per night from

$185

1 / 64

Responds fast! avg. 13 minutes

Price per night from

$200

1 / 27

The House Above the Barn

Aldie apartment

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$200

1 / 30

Ruby Summit Point - Your Home at the Track

Summit Point house

3 bedrooms / 1 bathroom / sleeps 6

“Convenience and Comfort at the Track” Ruby Summit Point is a great place to say with a group of friends over a track weekend. Very close to the track so no time wasted commuting to distant hotels. Very nicely upgraded kitchen and entire house. Beautif

Price per night from

$200

1 / 19

Restoration B&B - Washington Room

Paeonian Springs b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$165

1 / 22

Price per night from

$141

1 / 23

Burgundy room - Loudoun Valley Manor

Waterford b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 37 minutes

Price per night from

$95

1 / 18

Virginia Dreamer's Getaway

Warrenton room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$60

1 / 11

Suite Life in the Piedmont

Warrenton room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$75

1 / 7

Beautiful Suite w/Private Patio & Entrance In Wine & Horse Country

Haymarket house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$85

1 / 10
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