We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Waynesboro Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
50 rentals in Waynesboro.
Sort by:
Tripadvisor Sort

Shenandoah Valley Farm House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Large modern suite in Shenandoah Valley

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Inspired by Nature, relaxed cancellation policy, Safe & Immaculate

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Close to Wineries & Skyline Drive, Wintergreen, Enjoy Basic City location!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Spacious house located in Shenandoah Valley

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Close to Skyliine Drive Wintergreen Cozy and Private

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Reconnect with family & friends at our large, private, stylish Wintergreen home

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Perfect Sanctuary for Isolation and Relaxation!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
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
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

5 Star Luxury Home /Must Read Reviews

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful, Remodeled Cottage in the Heart of Afton

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

The Lewis Catherine House

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Pet-Friendly Wintergreen Home w/ Deck!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Oak Tree Cottage: a beautiful farm & mountain views.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful Wintergreen Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Afton Apt - Mins to Blue Ridge Pkway+Wineries

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Next Door to Veritas Vineyard Charlottesville-Afton Mountain Virginia

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Country escape in the heart of the Blue Ridge Mountains

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Beautiful Cottage at Historic Ramsay Estate with 'WOW' Blue Ridge views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Lavish Wintergreen Home w/Hot Tub by Skiing!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

NEW! Elegant Afton Getaway Near Trails & Vineyards

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Wintergreen Home w/Deck - Near Skiing & Hiking!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

CritzerShop - route 151- walk to the Brewey!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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
More info
Vrbo.com logo
Check-in
Check-out

NEW! Wintergreen Resort Cabin w/ 2 Decks & Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Secluded Nelson County Wine Country Bed & Breakfast In The Making

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Estate in Blue Ridge Foothills - 20 min to Charlottesville

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Fulton Belle Vue - Beautiful Farmhouse recently Renovated in Afton!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Paradise Mountain Estate

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Ramsay Estate | Carriage House w/ Mountain Views

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

Maren Estate (Mountain Estate 20 min to UVA)

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

WildManDan 1870 Farm house with Brewery onsite in Old Cola Barn

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

The Cottage At Rebel's Run Afton Mountain

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

The Cottage * Rebel’s Run Afton Mountain

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Waynesboro