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Greenwood Holiday Rentals

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50 rentals in Greenwood.
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Paradise Mountain Estate, holiday rental in Greenwood

Paradise Mountain Estate

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Sanctuary for Isolation and Relaxation!, holiday rental in Greenwood

Perfect Sanctuary for Isolation and Relaxation!

2 bedrooms
2 bathrooms
Sleeps 6
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Skyline Crest - Spectacular Blue Ridge Mountain Retreat, holiday rental in Greenwood

Skyline Crest - Spectacular Blue Ridge Mountain Retreat

2 bedrooms
2 bathrooms
Sleeps 6
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Shenandoah Valley Farm House, holiday rental in Greenwood

Shenandoah Valley Farm House

3 bedrooms
3 bathrooms
Sleeps 9
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Restored Double Log Cabin on 400 Mountain Acres, holiday rental in Greenwood

Restored Double Log Cabin on 400 Mountain Acres

4 bedrooms
4 bathrooms
Sleeps 17
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Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting, holiday rental in Greenwood

Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting

2 bedrooms
2 bathrooms
Sleeps 6
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Near Wineries & C'ville this is the perfect getaway space to relax & enjoy!, holiday rental in Greenwood

Near Wineries & C'ville this is the perfect getaway space to relax & enjoy!

2 bedrooms
1 bathroom
Sleeps 4
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A Must Stay Estate Located by Numerous Wineries & Breweries in Afton, Va, holiday rental in Greenwood

A Must Stay Estate Located by Numerous Wineries & Breweries in Afton, Va

5 bedrooms
5 bathrooms
Sleeps 13
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Beautiful newly renovated 3 bedroom/2 bath retreat for all seasons., holiday rental in Greenwood

Beautiful newly renovated 3 bedroom/2 bath retreat for all seasons.

3 bedrooms
2 bathrooms
Sleeps 6
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The Cottage at Sunnybank B&B, holiday rental in Greenwood

The Cottage at Sunnybank B&B

1 bedroom
1 bathroom
Sleeps 2
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Enjoy it all at Berry Hill Lake! Perfect for everyone!, holiday rental in Greenwood

Enjoy it all at Berry Hill Lake! Perfect for everyone!

4 bedrooms
4 bathrooms
Sleeps 12
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Ivy Springs Retreat. Private Lake,  pool, hot tub. Minutes from town & vineyards, holiday rental in Greenwood

Ivy Springs Retreat. Private Lake, pool, hot tub. Minutes from town & vineyards

5 bedrooms
7 bathrooms
Sleeps 18
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Peaceful Mountain Get Away, holiday rental in Greenwood

Peaceful Mountain Get Away

3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful, Remodeled Cottage in the Heart of Afton, holiday rental in Greenwood

Beautiful, Remodeled Cottage in the Heart of Afton

1 bedroom
1 bathroom
Sleeps 3
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The Lewis Catherine House, holiday rental in Greenwood

The Lewis Catherine House

5 bedrooms
5 bathrooms
Sleeps 12
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Large modern suite in Shenandoah Valley, holiday rental in Greenwood

Large modern suite in Shenandoah Valley

1 bedroom
1 bathroom
Sleeps 2
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Beautiful Wintergreen Retreat, holiday rental in Greenwood

Beautiful Wintergreen Retreat

4 bedrooms
3 bathrooms
Sleeps 12
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Oak Tree Cottage: a beautiful farm & mountain views., holiday rental in Greenwood

Oak Tree Cottage: a beautiful farm & mountain views.

4 bedrooms
2 bathrooms
Sleeps 9
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Rockfish Farmhouse - Beautiful Home In The Rockfish Valley, holiday rental in Greenwood

Rockfish Farmhouse - Beautiful Home In The Rockfish Valley

3 bedrooms
2 bathrooms
Sleeps 8
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Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries., holiday rental in Greenwood

Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries.

2 bedrooms
1 bathroom
Sleeps 4
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Authentic Log Cabin-  Available for Christmas due to last minute cancellation!, holiday rental in Greenwood

Authentic Log Cabin- Available for Christmas due to last minute cancellation!

4 bedrooms
2 bathrooms
Sleeps 10
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Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries, holiday rental in Greenwood

Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries

5 bedrooms
4 bathrooms
Sleeps 14
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CritzerShop - route 151- walk to the Brewey!, holiday rental in Greenwood

CritzerShop - route 151- walk to the Brewey!

4 bedrooms
2 bathrooms
Sleeps 8
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Stay at Knight's Gambit Vineyard, holiday rental in Greenwood

Stay at Knight's Gambit Vineyard

4 bedrooms
2 bathrooms
Sleeps 8
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Afton Mtn. Vineyards: Damy Cottage  Afton Mtn. Vineyards: Damy Cottage, holiday rental in Greenwood

Afton Mtn. Vineyards: Damy Cottage Afton Mtn. Vineyards: Damy Cottage

1 bedroom
1 bathroom
Sleeps 2
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2-Level Modern Home on 25 Private Acres with Amazing Mountain Views, holiday rental in Greenwood

2-Level Modern Home on 25 Private Acres with Amazing Mountain Views

3 bedrooms
3 bathrooms
Sleeps 10
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Inspired by Nature, relaxed cancellation policy, Safe & Immaculate, holiday rental in Greenwood

Inspired by Nature, relaxed cancellation policy, Safe & Immaculate

3 bedrooms
4 bathrooms
Sleeps 8
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Afton Mtn. Vineyards: Cadus Cottage  Afton Mtn. Vineyards: Cadus Cottage, holiday rental in Greenwood

Afton Mtn. Vineyards: Cadus Cottage Afton Mtn. Vineyards: Cadus Cottage

1 bedroom
1 bathroom
Sleeps 2
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Afton Mountain Vineyards Guest House  Afton Mountain Vineyards Guest House | Fre, holiday rental in Greenwood

Afton Mountain Vineyards Guest House Afton Mountain Vineyards Guest House | Fre

2 bedrooms
2 bathrooms
Sleeps 4
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Secluded Nelson County Wine Country Bed & Breakfast In The Making, holiday rental in Greenwood

Secluded Nelson County Wine Country Bed & Breakfast In The Making

3 bedrooms
2 bathrooms
Sleeps 8
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Afton Mtn. Vineyards: AnA Cottage  Afton Mtn. Vineyards: AnA Cottage, holiday rental in Greenwood

Afton Mtn. Vineyards: AnA Cottage Afton Mtn. Vineyards: AnA Cottage

1 bedroom
1 bathroom
Sleeps 2
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Minutes from UVA; Feel Like You're in the Country, holiday rental in Greenwood

Minutes from UVA; Feel Like You're in the Country

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Maren Estate (Mountain Estate 20 min to UVA), holiday rental in Greenwood

Maren Estate (Mountain Estate 20 min to UVA)

6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Fulton Belle Vue - Beautiful Farmhouse recently Renovated in Afton!, holiday rental in Greenwood

Fulton Belle Vue - Beautiful Farmhouse recently Renovated in Afton!

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn, holiday rental in Greenwood

WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn

5 bedrooms
4 bathrooms
Sleeps 10
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Spacious house located in Shenandoah Valley, holiday rental in Greenwood

Spacious house located in Shenandoah Valley

4 bedrooms
2 bathrooms
Sleeps 6
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Afton Mtn. Vineyards: Billon Cottage  Afton Mtn. Vineyards: Billon Cottage, holiday rental in Greenwood

Afton Mtn. Vineyards: Billon Cottage Afton Mtn. Vineyards: Billon Cottage

1 bedroom
1 bathroom
Sleeps 2
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Beautifully Located Cabin Near Blue Ridge Pkwy and Skyline Dr., holiday rental in Greenwood

Beautifully Located Cabin Near Blue Ridge Pkwy and Skyline Dr.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Lodge in Sugar Hollow, holiday rental in Greenwood

The Lodge in Sugar Hollow

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lavish Wintergreen Home w/Hot Tub by Skiing!, holiday rental in Greenwood

Lavish Wintergreen Home w/Hot Tub by Skiing!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Afton Apt - Mins to Blue Ridge Pkway+Wineries, holiday rental in Greenwood

Afton Apt - Mins to Blue Ridge Pkway+Wineries

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fully Furnished, Countryside Apt. near UVA; 2 Kings or King+2 Twins, holiday rental in Greenwood

Fully Furnished, Countryside Apt. near UVA; 2 Kings or King+2 Twins

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Family Home w/Yard & Patio, 1Mi to Vineyards!, holiday rental in Greenwood

NEW! Family Home w/Yard & Patio, 1Mi to Vineyards!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Farm Cottage in the Heart of Virginia's Wine Country!, holiday rental in Greenwood

Farm Cottage in the Heart of Virginia's Wine Country!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW! Elegant Afton Getaway Near Trails & Vineyards, holiday rental in Greenwood

NEW! Elegant Afton Getaway Near Trails & Vineyards

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Faber Home w/ Yard, Steps to Winery!, holiday rental in Greenwood

Spacious Faber Home w/ Yard, Steps to Winery!

4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Chic Afton Escape w/ Fire Pit: 2 Mi to Winery, holiday rental in Greenwood

NEW! Chic Afton Escape w/ Fire Pit: 2 Mi to Winery

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Log Cabin Escape on Delfosse Winery!, holiday rental in Greenwood

Romantic Log Cabin Escape on Delfosse Winery!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Beautiful Afton Farmhouse By Hikes & Wineries, holiday rental in Greenwood

NEW! Beautiful Afton Farmhouse By Hikes & Wineries

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Charming Home on 4 Acres Near Blue Ridge Pkwy, holiday rental in Greenwood

NEW! Charming Home on 4 Acres Near Blue Ridge Pkwy

5 bedrooms
4 bathrooms
Sleeps 8
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