House holiday rentals in Clarke County

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 15 acre estate of gardens and old barns. Close to wineries, breweries, the Appalachian and W&OD Trails and many historic villages (Middleburg, Upperville, Harpers Ferry) and only minutes from the Shenandoah River, this superbly decorated cottage is a wonderful get away from Washington DC and perfect for a couple or small family. Activities abound, or just visit local farmers’ markets and read.

The French Country Retreat *skyline, vineyards*

Looking for a romantic getaway, solo retreat, or chance to enjoy Front Royal's many wineries, hiking, and other attractions? This charming home features an open kitchen and cozy living area, a queen bedroom, and a small office with a twin bed and workspace. Unwind in the hot tub or bake cookies with hot chocolate for a touch of indulgence. This charming cottage offers a peaceful escape from your daily routine. Romantic décor for $300💕. Includes roses, candles, chocolates, balloons and bubbly.

Mount Weather Hideaway

Cozy and lovely furnished home nestled in the trees in the Blue Ridge Mtns, just down the road from the Appalachian Trail and Bear Chase Brewery, and only a few minutes from VA's finest vineyards. This unique retreat offers mountain living with all the comforts of a well-appointed home. Grill around the outdoor TV, get toasty around the firepit, enjoy relaxing in the hot tub -- all while your dogs run inside the fully-fenced in 1 acre. You'll fall in love with our Hideaway and the Blue Ridge!!

Beautiful Cottage in the Heart of Wine Country

Located at the crest of the Blueridge section of the Appalachian Mountains across from the Appalachian Trail and Bears Den, experience an incredible stay in the heart of Loudoun County wine country. Half a mile from Bear Chase brewery and minutes from Bluemont Vineyard, Dirt farm and others. If you like music Tally Ho in Leesburg has many great shows. Shopping and restaurants head to the quaint village of Middleburg, 25 minutes away. 50 minutes from Washington, DC. The views are stunning!

It's Own Destination/Farm Cottage with Mtn. Views

DESCRIPTION: Relax with family and friends at this peaceful picturesque retired farm. Panoramic mountain views surround this private living space close to Loudoun County's most beautiful wedding venues, wineries, breweries, agritourism adventures, the Shenandoah River, and Appalachian Trail. Nestled between Bluemont and Middleburg, VA. This farm cottage has been recently remodeled and updated with all new appliances and furnishings. It feels like home the minute you walk through the door.

Hot tub, prime leaf peeping and more! Gorgeous 4BR

This gorgeous chalet perched on a high hill is surrounded with trees and features an enormous wrap-around deck, HOT TUB, wood-burning fireplace, huge smart TVs and a GAME ROOM for adults and kids with every fun game you can imagine- pool, ping pong, PacMan video arcades, darts and more. Each bed is new and there are king beds and trundle beds to accommodate visitors of all ages. Please note there is an extra charge of $75 for first dog, $25/ea for 2nd/3rd (2nd/3rd dog fees charged later).

Deer Chase

Welcome to our renovated cabin, “Deer Chase”, incredibly convenient to Clarke County's Ruritan Fairgrounds, Rosemont Manor, wineries, breweries, Appalachian Trail, and more. This is just off Rte 7, located between Loudoun and Frederick Counties, less than 10 minutes to 81, in a private and relaxing setting. Looking for convenience to local amenities, in town for a wedding, Lucketts Fair, or Apple Blossom Festival, or just passing through and just need to kick your feet up, you found it.

Upperville Hunt Country Cottage

The home has a standing seam metal roof, clapboard-style siding, a stone foundation, a cozy front porch, and second-floor dormer windows. The interior is painted with warm colors and accented by antique oak barn wood paneling and trim in the family room. The flooring is the original antique heart pine. The cottage is decorated as a traditional English Hunt Box, with equine art and memorabilia, lovely antiques, warm carpets on the heart pine floors, and high-end bed linens.

The Ladybug Retreat

Welcome to the Ladybug Retreat! Nestled on 18+ wooded acres in Boyce, Virginia, this is the perfect spot for your group’s getaway. Our location offers a balance of seclusion and proximity to activities. We're less than 10 minutes from a state park, the Virginia State Arboretum, and a Shenandoah River boat ramp. Conveniently situated between historic Middleburg and vibrant Winchester, you’ll also have easy access to the area’s best vineyards, dining, and shops.