Farmstay holiday rentals in Jefferson County

Homestead 1870 in Wine Country

This cozy two-bedroom rustic farmhouse nestled in Virginia’s wine country and part of a working farm where guests can see farm animals. Close to local wineries, breweries, and delicious food. Located near Harper’s Ferry, the Appalachian Trail, and the Potomac River, perfect for hiking, kayaking, and exploring. Adventure parks and scenic trails are nearby, offering plenty of activities. Relax and enjoy farm life, local charm, and the beauty of Virginia's countryside from a well centered location.

#1 Cottage in Loudoun Co. (Lower of 2 units)w/pond

1st-floor apartment of a 2 unit Cape Cod Style Cottage with separate entrance and stone-floored sunroom/screen porch in front. This spacious 1 Bedroom, 1 Full Bathroom (complete full tub/shower combo) apartment is all you'll need to enjoy the best of Loudoun County. We're minutes from wineries, breweries, antiques, cultural & historical attractions, and much more. Not to mention our gorgeous 12-acre parcel of land with a huge pond that's stocked with all kinds of fish you can catch and release.

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Recently named a 2025 Silver Winner for Best Vacation Rental by WV Living magazine, this 1800s farmhouse is full of character and designed for comfort. The highlight is a heated saltwater plunge pool, open year-round, plus outdoor gathering spaces for summer and 3 fireplaces for cozy fall and winter stays. Guests rave about the incredibly comfortable beds! The Harpers Ferry area is a delight in every season, offering hiking, history, shopping, dining, river adventures, wineries and breweries.

Riverside Retreat on Shenandoah River

Quaint 3 bedroom cabin located on 1.5 acres with direct river access to the Shenandoah River. Great get away from the city! Fishing, tubing, kayaking, swimming, mountain biking, Appalachian/Rolling Ridge Foundation trail hiking, and campfires are within walking distance. Virginia wineries, breweries, white water rafting, casino/horse racing, car racing, Harpers Ferry and Charles Town historic sites are less than 30 mins. from the cabin. Or just listen to nature! Only 90 mins. from DC area.

Guest Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

Farwell Cottage c.1752 New Renovated Historic Home

This 250 year old stone house comes with old world charm and modern amenities. With complimentary farm fresh eggs, local bottle of wine and fiber high speed WiFi! Enjoy one of 3 fireplaces, 8 person dining room, sun room with complimentary coffee and tea, full kitchen. Take a moment to relax in the claw foot soaking tub. Or relax by our fire pit and have some fun with our complimentary s'more kit. Have a quiet movie night in our living room after fun day at wineries and breweries!

❤️ Secluded 1940s Romantic Tiny House on the River

Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 3 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

The Cabin at Blue Valley Farm

Come visit the Cabin at Blue Valley Farm! Located in the scenic “Between the Hills” valley in the foothills of Virginia’s Blue Ridge, the Farm features tranquility and beautiful views. The comfortable Cabin accommodates five with all the amenities of home. Nearby attractions include: historic Harper’s Ferry, hiking on the Appalachian trail, rafting and tubing on the Shenandoah and Potomac, fine dining, breweries, Catoctin Creek Distillery, and seven wineries within three miles.

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged with the exception of Wi-Fi - no satellite or TV. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

The Cuckoo Chalet

We invite you to come stay "just up the mountain" from historic Harpers Ferry National Park. The Cuckoo Chalet is our happy place and a labor of love. Enjoy 3 bedrooms with queen beds (plus one twin bed and additional twin mattresses without frames upon request) and 2 bathrooms. Make yourself at home in our indoor and outdoor gathering spaces. Grill out, enjoy the fire pit, tube the river, watch for deer, hike trails, play pool or read a good book in the hammock.

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

MOUNTAIN MAMA VACATION HOMES & CABINS Experience the charm of one of the oldest homes in Loudoun! Built in 1752, this historic home retains the original log/exposed brick walls, wood floors, ceiling beams, and antique stone fireplaces. The home is sited on a hillside with sweeping views of the 66 acre vineyard, which is actively being cultivated for wine production. Enjoy a glass yourself by the large swimming pool as you take in the sunsets over the vineyard.

Modern, private cottage at Fairview Organic Farm

Discounts for stays of 5 nights or more. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the newish cottage is surrounded by pasture, organic gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Enjoy sun rise from the deck and sunsets from the porch.