
Guesthouse vacation rentals in Jefferson County
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Top-rated guesthouse rentals in Jefferson County
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Jefferson County guesthouse rentals
Family-friendly guest house rentals

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
Guest house rentals 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
Guest house rentals with a washer and dryer

Skyhorse Retreat Guest House

The Nest on Nixon Road

The Tuberose Suite

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

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
- Rentals with lake access Jefferson County
- Waterfront rentals Jefferson County
- Rentals with an EV charger Jefferson County
- Rentals with a patio Jefferson County
- Rentals with a fire pit Jefferson County
- Kid-friendly rentals Jefferson County
- Family-friendly rentals Jefferson County
- Cottage rentals Jefferson County
- Rentals with a washer and dryer Jefferson County
- Farmstay rentals Jefferson County
- Cabin rentals Jefferson County
- Rentals with pools Jefferson County
- Rentals with a kayak Jefferson County
- Fitness-friendly rentals Jefferson County
- Rentals with a fireplace Jefferson County
- Pet-friendly rentals Jefferson County
- House rentals Jefferson County
- Rentals with breakfast Jefferson County
- Bed and breakfasts Jefferson County
- Apartment rentals Jefferson County
- Rentals with a hot tub Jefferson County
- Rentals with outdoor seating Jefferson County
- Private suite rentals Jefferson County
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- Cunningham Falls State Park
- Stone Tower Winery
- Great Falls Park
- Caledonia State Park
- Cowans Gap State Park
- Cacapon Resort State Park
- The Links at Gettysburg
- Robert Trent Jones Golf Club
- Gambrill State Park
- Congressional Country Club
- Liberty Mountain Resort
- Whiskey Creek Golf Club
- Field of Screams Maryland
- South Mountain State Park
- Creighton Farms
- Sly Fox Golf Club
- Shenandoah Valley Golf Club
- Berkeley Springs State Park
- Chevy Chase Club
- Columbia Country Club
- Whitetail Resort
- Bowling Green Country Club
- Notaviva Vineyards
- Washington Golf & Country Club