
Holiday rentals in Stuarts Draft
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Top-rated holiday rentals in Stuarts Draft
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Staunton Escape 👑King Bd, washer+dryer+Wifi+Fence
This 2 story house with vaulted ceilings is situated close to downtown Staunton in the heart of the Shenandoah Valley. Access to Shenandoah Nation Park and the Blue Ridge Parkway is just a short drive. This unique space has a King and Queen bed on the 1st floor, and a twin bed, futon, sofa bed and section on the 2nd floor. The ample parking allows for multiple large vehicles. The yard has a covered seating area and is completely fenced in. Wifi is fast, 58in smart TV, hand crafted decor, privacy
FamilyLocationTV
4.9 out of 5 average rating, 237 reviews
Willow Grove-Hot Tub-Wineries-Breweries-Hiking
Relax at Willow Grove Home, a peaceful, pet-friendly retreat on 3.5 private acres with mountain views, stunning sunsets, and a hot tub. Enjoy the fire pit with complimentary firewood, bistro-lit patio, outdoor dining and games. Features include fiber optic internet, TVs in every bedroom, a 65" TV with surround sound, Sleep Number and Nectar beds, well-stocked kitchen, and dining and dinnerware for up to 20 guests. Convenient to wineries, breweries, hiking, caverns, wedding venues, JMU, and UVA.
FamilyLocationLong stay
4.97 out of 5 average rating, 103 reviews
Bee & Key—Staunton downtown
This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. in downtown Staunton. 2BR/1BA can sleep up to 6 if you don’t mind being cozy! • king bed in main bedroom (2) • day bed with trundle in small adjoining bedroom (2) • sofa bed in living room (1) • good air mattress (1) Bee & Key is a few steps from the restaurants and shops of our vibrant downtown, plus Blackfriar’s Playhouse, Woodrow Wilson Museum, Mary Baldwin University and the Amtrak station.
ValueFamilyGetting around
4.96 out of 5 average rating, 312 reviews
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.
ValueLocationCheckout
4.99 out of 5 average rating, 440 reviews
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.
LocationFamilyCheck-in
4.99 out of 5 average rating, 111 reviews
Sunrise Casita: a tiny house at Cana Barn
Our 250 sq ft tiny house was built by our talented craftswoman Kara. We used wood from our property and reclaimed materials to create a cozy and unique getaway. The front porch looks out to a beautiful view of the Blue Ridge Mountains and looks up to a local vintage sign. We are LGBTQ+ welcoming. Sunrise to us is the embodiment of a fresh start and a new opportunity. It is hope and possibility, adventure and inspiration, beauty and wonder. We hope all of this for your stay in our tiny house!
ValueLocationRiver
4.95 out of 5 average rating, 201 reviews
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.
LocationValueView
4.98 out of 5 average rating, 121 reviews
The Sanctuary
Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!
LocationValueIndoor spaces
4.99 out of 5 average rating, 377 reviews
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.
ValueFamilyIndoor spaces
4.93 out of 5 average rating, 411 reviews
The Stable
Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.
FamilyValueCheckout
4.92 out of 5 average rating, 491 reviews
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.
LocationValueView
4.9 out of 5 average rating, 450 reviews
Prickly Pear Cottage *5 minutes from skyline dr.*
Prickly Pear Cottage is located right at the base of Afton mountain in Waynesboro. You’re just minutes from hiking, breweries and vineyards! This home was designed with the traveler in mind. You will love the spacious great room, large rec room in the basement outdoor space for your furry friends and the kids.
FamilyValueComfort
4.85 out of 5 average rating, 213 reviewsPopular amenities for Stuarts Draft holiday rentals
Other great holiday rentals in Stuarts Draft

The Copper Cottage - near the Appalachian Trail
FamilyValueHiking
4.89 out of 5 average rating, 340 reviews
Peacefield: Farmhouse in the Shenandoah Valley
LocationFamilyOutdoor spaces
4.97 out of 5 average rating, 77 reviews
Books n Bears
LocationFamilyAmenities
4.93 out of 5 average rating, 30 reviews
Modern 5BR Home | Spacious Getaway in the Valley
ValueFamilyHiking
4.82 out of 5 average rating, 56 reviews
Cozy Farm Retreat
ValueFamilySleep quality
4.95 out of 5 average rating, 39 reviews
Nona's Cottage – Waynesboro/Shenandoah Valley, VA
ValueLocationBathroom
4.92 out of 5 average rating, 93 reviews
Spacious 2BR Apartment w/ Pool & Fenced Yard
LocationValueIndoor spaces
4.94 out of 5 average rating, 36 reviews
"Virginia Beauty" in Historic Tree Streets
ValueFamilyGetting around
4.98 out of 5 average rating, 58 reviewsDestinations to explore
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- Shenandoah National Park
- Early Mountain Winery
- University of Virginia
- Monticello
- Devils Backbone Brewing Co Basecamp
- Wintergreen Resort
- Glass House Winery
- James Madison University
- Cardinal Point Winery
- Blenheim Vineyards
- Virginia Horse Center
- Natural Bridge State Park
- The Rotunda
- Downtown Mall
- Liberty Mountain Snowflex Centre
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Frontier Culture Museum
- John Paul Jones Arena
- IX Art Park
- Grand Caverns
- James Monroe's Highland
- James River State Park
- Massanutten Indoor WaterPark
- Appomattox Court House National Historical Park





