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Waynesboro Vacation Rentals

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50 rentals in Waynesboro.
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Shenandoah Valley Farm House, vacation rental in Waynesboro

Shenandoah Valley Farm House

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Large modern suite in Shenandoah Valley, vacation rental in Waynesboro

Large modern suite in Shenandoah Valley

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Inspired by Nature, relaxed cancellation policy, Safe & Immaculate, vacation rental in Waynesboro

Inspired by Nature, relaxed cancellation policy, Safe & Immaculate

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious house located in Shenandoah Valley, vacation rental in Waynesboro

Spacious house located in Shenandoah Valley

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Sanctuary for Isolation and Relaxation!, vacation rental in Waynesboro

Perfect Sanctuary for Isolation and Relaxation!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting, vacation rental in Waynesboro

Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Marley's Cabin in Wintergreen, VA, vacation rental in Waynesboro

Marley's Cabin in Wintergreen, VA

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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5 Star Luxury Home /Must Read Reviews, vacation rental in Waynesboro

5 Star Luxury Home /Must Read Reviews

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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A Must Stay Estate Located by Numerous Wineries & Breweries in Afton, Va, vacation rental in Waynesboro

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

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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The Lewis Catherine House, vacation rental in Waynesboro

The Lewis Catherine House

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, Remodeled Cottage in the Heart of Afton, vacation rental in Waynesboro

Beautiful, Remodeled Cottage in the Heart of Afton

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Wintergreen Retreat, vacation rental in Waynesboro

Beautiful Wintergreen Retreat

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries., vacation rental in Waynesboro

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oak Tree Cottage: a beautiful farm & mountain views., vacation rental in Waynesboro

Oak Tree Cottage: a beautiful farm & mountain views.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Rockfish Farmhouse - Beautiful Home In The Rockfish Valley, vacation rental in Waynesboro

Rockfish Farmhouse - Beautiful Home In The Rockfish Valley

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Authentic Log Cabin-  Available for Christmas due to last minute cancellation!, vacation rental in Waynesboro

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries, vacation rental in Waynesboro

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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BEAUTIFUL HOUSE IN WINTERGREEN RESORT. ACROSS FROM SUMMER POOL/PICNIC PAVILION., vacation rental in Waynesboro

BEAUTIFUL HOUSE IN WINTERGREEN RESORT. ACROSS FROM SUMMER POOL/PICNIC PAVILION.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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CritzerShop - route 151- walk to the Brewey!, vacation rental in Waynesboro

CritzerShop - route 151- walk to the Brewey!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy winter on the mountain in our 4 bdrm/2 bath cabin!  Ski season is here!!!!, vacation rental in Waynesboro

Enjoy winter on the mountain in our 4 bdrm/2 bath cabin! Ski season is here!!!!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Afton Mtn. Vineyards: Damy Cottage  Afton Mtn. Vineyards: Damy Cottage, vacation rental in Waynesboro

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2-Level Modern Home on 25 Private Acres with Amazing Mountain Views, vacation rental in Waynesboro

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

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mountain view with quick access to skiing, hiking, breweries, wineries, and more, vacation rental in Waynesboro

Mountain view with quick access to skiing, hiking, breweries, wineries, and more

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Afton Mtn. Vineyards: Cadus Cottage  Afton Mtn. Vineyards: Cadus Cottage, vacation rental in Waynesboro

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Afton Mountain Vineyards Guest House  Afton Mountain Vineyards Guest House | Fre, vacation rental in Waynesboro

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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July Available: Luxury Mountain House on Golf Course w/ Resort Membership, vacation rental in Waynesboro

July Available: Luxury Mountain House on Golf Course w/ Resort Membership

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious new apt. with hot tub, mountain views, stream & fishing pond on 25 acre, vacation rental in Waynesboro

Spacious new apt. with hot tub, mountain views, stream & fishing pond on 25 acre

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Preferring rentals of 3 wks or more.  $390. per wk.  3 week minimum.  Dogs free., vacation rental in Waynesboro

Preferring rentals of 3 wks or more. $390. per wk. 3 week minimum. Dogs free.

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Nelson County Wine Country Bed & Breakfast In The Making, vacation rental in Waynesboro

Secluded Nelson County Wine Country Bed & Breakfast In The Making

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Paradise Mountain Estate, vacation rental in Waynesboro

Paradise Mountain Estate

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!, vacation rental in Waynesboro

Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Afton Mtn. Vineyards: AnA Cottage  Afton Mtn. Vineyards: AnA Cottage, vacation rental in Waynesboro

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Maren Estate (Mountain Estate 20 min to UVA), vacation rental in Waynesboro

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!, vacation rental in Waynesboro

Fulton Belle Vue - Beautiful Farmhouse recently Renovated in Afton!

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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The Retreat at Wintergreen, vacation rental in Waynesboro

The Retreat at Wintergreen

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn, vacation rental in Waynesboro

WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Pet-Friendly Wintergreen Home w/ Deck!, vacation rental in Waynesboro

Pet-Friendly Wintergreen Home w/ Deck!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Afton Mtn. Vineyards: Billon Cottage  Afton Mtn. Vineyards: Billon Cottage, vacation rental in Waynesboro

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lavish Wintergreen Home w/Hot Tub by Skiing!, vacation rental in Waynesboro

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, vacation rental in Waynesboro

Afton Apt - Mins to Blue Ridge Pkway+Wineries

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wintergreen Home w/ Deck - Near Skiing & Hiking!, vacation rental in Waynesboro

Wintergreen Home w/ Deck - Near Skiing & Hiking!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Family Home w/Yard & Patio, 1Mi to Vineyards!, vacation rental in Waynesboro

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

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen Resort Cabin w/ 2 Decks & Hot Tub!, vacation rental in Waynesboro

Wintergreen Resort Cabin w/ 2 Decks & Hot Tub!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farm Cottage in the Heart of Virginia's Wine Country!, vacation rental in Waynesboro

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, vacation rental in Waynesboro

NEW! Elegant Afton Getaway Near Trails & Vineyards

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Chic Afton Escape w/ Fire Pit: 2 Mi to Winery, vacation rental in Waynesboro

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Wintergreen Resort Mtn Hideaway: 2 Mi to Ski!, vacation rental in Waynesboro

NEW! Wintergreen Resort Mtn Hideaway: 2 Mi to Ski!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Beautiful Afton Farmhouse By Hikes & Wineries, vacation rental in Waynesboro

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, vacation rental in Waynesboro

NEW! Charming Home on 4 Acres Near Blue Ridge Pkwy

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Wintergreen Resort Escape Near Leaf Peeping!, vacation rental in Waynesboro

NEW! Wintergreen Resort Escape Near Leaf Peeping!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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