Upperville Vacation Rentals, Houses & More


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1 / 5

Cute 2BR/2BA Cottage in Virginia's Hunt Country

  • 2
  • 4
  • 2 nights min

$195

Details

Great rentals within 30 miles that match your search

1 / 24

NEW! 'Anny's Farm House' 4BR Round Hill House

  • 4
  • 8
  • Min stay varies

$285

Details

1 / 5

Wine Country Retreat 60 miles from DC

  • 4
  • 12
  • 2 nights min

$395

Details

2
1 / 17

TyroleanGardenSuite/prvt wiz patio in art villa

  • 1
  • 2
  • 1 night min

$150

Details

4
1 / 26

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

  • 1
  • 3
  • 1 night min

$165

Details

2
1 / 15

The Van Gogh Room in Private Villa

  • 1
  • 2
  • 1 night min

$125

Details

1 / 47

Hot tub, wifi, walk to the trails, vineyards, large deck, large outdoor area!

  • 2
  • 4
  • 2 nights min

$175

Details

3
1 / 72

Charming Historic Home in Shenandoah Valley Wine Country near Skyline Drive

  • 5
  • 14
  • 2 nights min

$220

Details

1 / 25

Idyllic Restored 18c cottage, Views*All Amenities.

  • 2
  • 3
  • 7 nights min

$122

Details

10
1 / 27

Valley Vista Cabin - ShenandoahRiver view & hottub

  • 3
  • 6
  • Min stay varies

$205

Details

49
1 / 45

Rainbow View Cabin - ShenandoahValleyview & hottub

  • 2
  • 4
  • Min stay varies

$155

Details

1
1 / 24

Vista Magnifique, a private 50 acre mountain-top estate in wine country

  • 3
  • 6
  • 2 nights min

$500

Details

1 / 24

Alluring 3BR Purcellville Townhome w/Wifi, Gas Grill & Private Backyard Patio

  • 3
  • 6
  • 3 nights min

$135

Details

10
1 / 65

Celebration™ Retreat! a fun venue in Wine Country

  • 4
  • 18
  • 1 night min

$245

Details

8
1 / 19

Ruby Summit Point - Your Home at the Track

  • 3
  • 6
  • 2 nights min

$200

Details

1
1 / 16

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

  • 1
  • 2
  • 1 night min

$75

Details

2
1 / 15

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

  • 1
  • 2
  • 1 night min

$85

Details

1 / 23

Golden Room at Loudoun Valley Manor near Leesburg

  • 1
  • 2
  • 1 night min

$96

Details

1 / 28

Franklin Manor - Close to Front Royal and Attractions

  • 4
  • 6
  • 2 nights min

$275

Details

1 / 25

Gorgeous and Private

  • 5
  • 9
  • 1 night min

$382

Details

1 / 4

Cozy Leesburg Cottage

  • 1
  • 2
  • 1 night min

$65

Details

1 / 6

Charming Carriage House Near Historic Waterford VA

  • 2
  • 4
  • 2 nights min

$195

Details

5
1 / 11

Beautiful home in the heart of Old Town Winchester

  • 3
  • 8
  • 2 nights min

$210

Details

1
1 / 19

Just Like Heaven Carriage House

  • 1
  • 2
  • 1 night min

$125

Details

1 / 4

Sheraton Vistiana

  • 2
  • 6
  • 7 nights min

$179

Details

1 / 12

Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery

  • 1
  • 4
  • 1 night min

$99

Details

1 / 15

Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town

  • 2
  • 5
  • 1 night min

$99

Details

1 / 15

Gorgeous luxury house in Ashburn

  • 4
  • 8
  • 1 night min

$289

Details

1 / 29

Poe's Lodge: 25 acres, VA wine country, total privacy!

  • 3
  • 6
  • 1 night min

$275

Details

4
1 / 30

The King Mountain House

  • 3
  • 8
  • 2 nights min

$250

Details

1
1 / 10

2BDRM Skyline Ranch Chalet Summer Vacation

  • 2
  • 6
  • 7 nights min

$122

Details

12
1 / 38

Adventure Inn - Historic Home with Hot Tub, close

  • 4
  • 14
  • 2 nights min

$325

Details

1 / 71

Luxury One Loudoun Home

  • 4
  • 8
  • 2 nights min

$450

Details

1 / 39

Luxury One Loudoun Condo

  • 3
  • 5
  • 2 nights min

$300

Details

2
1 / 5

Gorgeous Mountain Views - Walk to historic town

  • 3
  • 6
  • 2 nights min

$225

Details

5
1 / 15

Two Rivers Guest House. Walk to rivers, parks, downtown and restaurants

  • 2
  • 6
  • 2 nights min

$240

Details

1 / 6

Marbrun House in Historic Harpers Ferry

  • 1
  • 2
  • 1 night min

$75

Details

1 / 15

Absolute Perfect Retreat-Log Cabin with Wrap around deck

  • 3
  • 10
  • 2 nights min

$275

Details

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