Holiday rentals in Waynesboro

Gameroom~Gym~Walk to River & Downtown~BR Pkwy 5mi

Centrally located historic home walkable to river, downtown shops & restaurants. Less than 15 mins to Shenandoah Natl Park, Blue Ridge Pkwy, Skyline Drive, Blue Ridge Tunnel Hike, Basic City Brewery, The Foundry, Wineries, Antique shops & Augusta Expo. Charlottesville, Staunton, Harrisonburg & Nelson Ski/Wineries 30mi The rec center across the street has playground & basketball court. Home has a main level bed & bath, game room, gym, 2 living rooms, firepit, fireplace, king bed & lots of charm!

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

Modern 5BR Home | Spacious Getaway in the Valley

Welcome the Shenandoah Valley! This spacious, peaceful home is perfect for families, groups, or business stays. Enjoy modern amenities, cozy furnishings, and plenty of space to relax. 🛏5 Bedrooms | 2 Full & 2 Half Bathrooms – Sleeps 12 🍽Fully Equipped Kitchen – Cook & dine together 🛋Open Living Area – Great for gatherings 🚗Ample Parking 📍Near: Blue Ridge Parkway, Humpback Rock, Shenandoah National Park, Skyline Drive, Blue Mountain Brewery, Starr Hill, Pro Re Nata, King Family Vineyards.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

Simple Comfort

Simple Comfort is located in historic Waynesboro, Virginia. We are in a quiet neighborhood, away from the busy highways and all their noise. Its an older neighborhood, but we find it simple and comfortable – our hope is that you will too. Once here you are 10 minutes from Shenandoah National Park, 10 minutes from the Blue Ridge Parkway and 10 minutes from the Appalachian Trail. We are also 30 minutes from the University of Virginia campus. It’s just over the mountain on Interstate 64.

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! At the entrance to downtown Historic Waynesboro and the riverside park, its restaurants and stores can entertain even the peculiar palate or collector, some are right across the street! Fully fenced in back yard, so bring the pups to play!

Cute Place in Waynesboro

Comfortable new home built last year. The house has 3 bedrooms with queen size beds. Living room and master bedroom with TV's you can stream your favorite shows. Less than 40 minutes to Wintergreen or Massanutten ski resort/water park. Just 5 minutes to Blue Ridge Parkway and many hiking trails/cycling. Numerous Breweries or wineries. Only 30 minutes from Charlottesville. Minutes from quality restaurants, local and national chains. Walking distance to one of the local parks.

"Virginia Beauty" in Historic Tree Streets

Tranquility meets beauty at this historic home located within minutes of the Blue Ridge Parkway, Shenandoah National Park, Wintergreen, and countless wineries and breweries. The entire home and spacious yard are yours to enjoy. Relax in the newly updated rooms decorated with lovely art. Fully stocked kitchen, fast WiFi, and two porches. A 10-minute walk will take you to downtown Waynesboro, restaurants, coffee shops, and the two-mile Greenway Trail on the South River.

Shenandoah Gateway | Renovated 3BR Home

Welcome to your Shenandoah Valley getaway! This 3-bedroom, 2-bath home in Waynesboro backs up to the national forest and offers the perfect base for exploring Virginia's mountains, wineries, breweries, and charming towns. Located just minutes from Skyline Drive, 20 minutes from Charlottesville and Staunton, this spacious retreat combines modern comfort with easy access to outdoor adventure.

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.