House holiday rentals in Waynesboro

Glass House | Mountain & Water Views @ Wintergreen

This custom home at the base of Wintergreen is located 40-minutes from Charlottesville. The waterside setting offers views from living, primary bedrooms, decks and porches, as well as upstairs bedroom and balcony. Large glass walls and sliding doors ensure connection with the landscape. A two-person master-bathroom shower with views of the pond is a key feature of the home's sleek and minimalist design. The home is off of the Rte. 151 beer/wine/distillery trail and nestled beside a golf course.

Cabin in Woods | Family & Dog Friendly | Fire Pit

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature retreat - Outdoor patio & fire pit - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

River Views HOT TUB, WIFI, near Buc ee’s and I81!

Come relax in the hot tub and enjoy this peaceful getaway right on North River. We are tucked away in the countryside but just 5 minutes from I81 as well as 10 min to Bridgewater College, 15 min to Blue Ridge Community College, 17 min to JMU, and 25 minutes to Massanutten Resort. There are plenty of exciting adventures here in the heart of the Shenandoah Valley including, hiking, wineries, shopping, and lots of good food! We are just minutes from Buc-cee’s Rockingham location!!

* Award-Winning Renovation * Ideal Location *

— Ample Parking in Driveway & Adjacent Private Parking Lot — Cleaning & Linens taken care of for you — Prepare a meal in the fully equipped kitchen. Relax on the porch as the sun sets behind the nearby mountains. Or sink into your own king-size bed with a good book. This downtown home was painstakingly renovated to highlight its historic character and is a proud recipient of the Historic Staunton Foundation's 2021 Residential Rehabilitation Award. Welcome to NEWTOWN RETREAT!

Hot Tub - Fire Pit - Game Room

Howdy! Nestled perfectly between the North Terminus of the Blue Ridge Parkway, the entrance to Skyline Drive, all of the Afton wineries, the Beerwerks Trail, Wintergreen Resort, and Downtown Waynesboro, this four bedroom house with a fully stocked game room, two patios, a fire pit, and hot tub is the perfect spot to relax after a long day of enjoying the Shenandoah Valley.

Ridgeview Retreat: Mountain Views and Pet Friendly

Ridgeview Retreat is a cozy cabin situated beautifully on over 15 sprawling acres with gorgeous mountain views. Enjoy the peace and quiet of the country, but also proximity to Downtown Staunton and easy access to Harrisonburg. This 3 bedroom cabin sleeps 7 and boasts gorgeous outdoor spaces with a firepit, swings, and land to roam.

Blackwood Air B & B

Enjoy this spacious dwelling while viewing the Blue Ridge Mountains, Watch the freight train make its way around the curve or listen to the sheep as they graze in the pasture. Nearby outdoor activities are various hiking trails, Skyline Drive Parkway, or a local Shenandoah Acres lake. Only 10 miles from Wintergreen Resort.