
Guesthouse vacation rentals in Jefferson County
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Top-rated guesthouses in Jefferson County
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Jefferson County guesthouses
Family-friendly guesthouses

Stylish 1 Bedroom Studio Middleburg

Mt. Home Cabbin - Second Floor

The Shady Bear Cabin

CozyLeesburgCottage-Private Home Downtown Leesburg

"Cabbin" at Mountain Home B&B

Jewel Vinsota Artist's Guesthouse

Terrapin Cabin. A sunny, quiet cabin in the woods.

City Dog Farm
Guesthouses with a patio

Mountain Retreat | Hot Tub • Pool • Views • Trails

Ventura Cottage: 360-views/HotTub/4 acres/Gym

The Cottage

The Patent House

A lovely cottage in The Plains, Virginia

18th Century Middleburg Cottage

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

Blueridge Mountain Guest Cabin- Amongst the Trees
Guesthouse rentals with a washer and dryer

Skyhorse Retreat Guest House

The Nest on Nixon Road

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

The Tuberose Suite

Trailside Chalet (A storybook chalet with hot tub)

Private 2 BR, 1 Bath Carriage House Near Wineries!

Cottage Escape in Virginia Wine Country

Lovely spacious one-bedroom guest house
Destinations to explore
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- Great Falls Park
- Cunningham Falls State Park
- Caledonia State Park
- Stone Tower Winery
- Cowans Gap State Park
- Cacapon Resort State Park
- The Links at Gettysburg
- Robert Trent Jones Golf Club
- Congressional Country Club
- Liberty Mountain Resort
- Gambrill State Park
- Whiskey Creek Golf Club
- South Mountain State Park
- Shenandoah Valley Golf Club
- Field of Screams Maryland
- Berkeley Springs State Park
- Sly Fox Golf Club
- Creighton Farms
- Whitetail Resort
- Columbia Country Club
- Bowling Green Country Club
- Notaviva Vineyards
- Washington Golf & Country Club
- Twin Lakes Golf Course