Waynesboro Holiday Rentals
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50 rentals in Waynesboro.
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Shenandoah Valley Farm House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Large modern suite in Shenandoah Valley
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Inspired by Nature, relaxed cancellation policy, Safe & Immaculate
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Close to Wineries & Skyline Drive, Wintergreen, Enjoy Basic City location!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spacious house located in Shenandoah Valley
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Close to Skyliine Drive Wintergreen Cozy and Private
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Reconnect with family & friends at our large, private, stylish Wintergreen home
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Perfect Sanctuary for Isolation and Relaxation!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Save time - get the best Waynesboro rentals sent straight to your email!
In the center of Nelson County's wine and beer region, 19 miles to UVA/Cville
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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A Must Stay Estate Located by Numerous Wineries & Breweries in Afton, Va
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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5 Star Luxury Home /Must Read Reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful, Remodeled Cottage in the Heart of Afton
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Lewis Catherine House
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Pet-Friendly Wintergreen Home w/ Deck!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Oak Tree Cottage: a beautiful farm & mountain views.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Wintergreen Retreat
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Afton Apt - Mins to Blue Ridge Pkway+Wineries
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Next Door to Veritas Vineyard Charlottesville-Afton Mountain Virginia
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2-Level Modern Home on 25 Private Acres with Amazing Mountain Views
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Afton Mtn. Vineyards: Cadus Cottage Afton Mtn. Vineyards: Cadus Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Country escape in the heart of the Blue Ridge Mountains
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Authentic Log Cabin- Available for Christmas due to last minute cancellation!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Cottage at Historic Ramsay Estate with 'WOW' Blue Ridge views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Afton Mtn. Vineyards: Damy Cottage Afton Mtn. Vineyards: Damy Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Mountain view with quick access to skiing, hiking, breweries, wineries, and more
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Afton Mtn. Vineyards: Billon Cottage Afton Mtn. Vineyards: Billon Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lavish Wintergreen Home w/Hot Tub by Skiing!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Family Home w/Yard & Patio, 1Mi to Vineyards!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Elegant Afton Getaway Near Trails & Vineyards
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wintergreen Home w/Deck - Near Skiing & Hiking!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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CritzerShop - route 151- walk to the Brewey!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Afton Mtn. Vineyards: AnA Cottage Afton Mtn. Vineyards: AnA Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Afton Mountain Vineyards Guest House Afton Mountain Vineyards Guest House | Fre
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Preferring rentals of 3 wks or more. $390. per wk. 3 week minimum. Dogs free.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Wintergreen Resort Cabin w/ 2 Decks & Hot Tub
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Nelson County Wine Country Bed & Breakfast In The Making
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Estate in Blue Ridge Foothills - 20 min to Charlottesville
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Fulton Belle Vue - Beautiful Farmhouse recently Renovated in Afton!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Paradise Mountain Estate
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ramsay Estate | Carriage House w/ Mountain Views
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Maren Estate (Mountain Estate 20 min to UVA)
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Farm Cottage in the Heart of Virginia's Wine Country!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Cottage At Rebel's Run Afton Mountain
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Cottage * Rebel’s Run Afton Mountain
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Frequently Asked Questions about Waynesboro
- Yes, here are some popular holiday rentals in Waynesboro that have a pool:\n
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- Spacious house located in Shenandoah Valley \n
- Large modern suite in Shenandoah Valley \n
- Shenandoah Valley Farm House \n
- Yes, here are some popular holiday rentals in Waynesboro that have internet access:\n
- \n
- Spacious house located in Shenandoah Valley \n
- Large modern suite in Shenandoah Valley \n
- Shenandoah Valley Farm House \n
- The best pet friendly rentals in Waynesboro are:\n
- \n
- Spacious house located in Shenandoah Valley \n
- Large modern suite in Shenandoah Valley \n
- Shenandoah Valley Farm House \n
- Some of the most popular kid friendly rentals in Waynesboro are:\n
- \n
- Spacious house located in Shenandoah Valley \n
- Large modern suite in Shenandoah Valley \n
- Shenandoah Valley Farm House \n