House holiday rentals in Clarke County

4.87 out of 5 average rating, 229 reviews

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 50 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.

5 out of 5 average rating, 54 reviews

Home in Berryville

The Hill House at Stubblefield

Enjoy spectacular views of the Blue Ridge from this meticulously crafted stone house. The Hill House is situated on 40 acres in beautiful Clarke County, Virginia, and offers easy access to any outdoor activity your heart desires. This getaway is 2 miles from a public boat landing, and is surrounded by pastoral views and country roads in all directions. The Hill House is on Stubblefield Farm, which has its origins dating back to 1792. Come enjoy local wineries, breweries, and antique shops.

4.92 out of 5 average rating, 24 reviews

Home in Front Royal

New | The Rosewood Retreat | Cozy Cabin w/ Hot Tub

Looking for a romantic getaway, solo retreat, or chance to enjoy Front Royal's many wineries, hiking, and other attractions? "The Royal Cabin" 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 cabin offers a peaceful escape from your daily routine. Romantic décor for $300💕. Includes roses, candles, chocolates, balloons and bubbly.

4.89 out of 5 average rating, 110 reviews

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!

4.93 out of 5 average rating, 44 reviews

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.

4.94 out of 5 average rating, 179 reviews

Home in Front Royal

Hot tub w/ Sunset Views! Secluded mountain chalet!

Secluded chalet near the top of a mountain on 8 acres, just 70 minutes from downtown DC, 20 minutes to old town Front Royal, close enough to get Instacart from groceries, Costco and Target, and private enough to enjoy your sunset view from the deck every night and to not see any other homes! The home is at the end of a long gravel road and parking in a small cul-de-sac. Dogs are allowed for a $75 fee per stay for the 1st, $25 after, up to 3 dogs max, extra fees charged after reservation.

4.99 out of 5 average rating, 76 reviews

Historic Bluemont Village Home

This home is located in the historic village of Bluemont, VA at the foothills of the Blue Ridge Mountains. Quiet and comfortable, situated on a beautiful property overlooking the Loudoun Valley, enjoy a taste of the country and mountain life only 60 miles from Washington, DC. In the heart of VA's wine country, easily accessible to vineyards, breweries, and other activities. For adventurous guests, the Appalachian Trail and Shenandoah River are within minutes. Pleasant to visit year round.

4.97 out of 5 average rating, 199 reviews

Home in Winchester

Colonial Getaway Near Old Town Historic Winchester

Colonial style home- enjoy a spacious home with large living room, dining room, kitchen, 3 bedrooms and 2.5 bathrooms. Perfect for a family or a longer stay. Just a few miles drive to Old Town Winchester which includes numerous restaurants, bars, shopping and some kind of event... like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. Near by to other scenic attractions as well- Shenandoah National Park, Luray Caverns, and Harper's Ferry!

4.99 out of 5 average rating, 77 reviews

Home in Berryville

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.

4.94 out of 5 average rating, 31 reviews

Home in Upperville

Raspberry Repose

This home exudes a sense of seclusion and tranquility, making it an ideal hideaway for those seeking a break from the hustle and bustle of everyday life. Situated on a sprawling 10-acre property, the home is enveloped by nature's beauty, offering a peaceful and rejuvenating atmosphere. Enjoy relaxing in the soaking tub and gazing at the stars while you sit by the fire pit. Located just an hour from DC, 12 minutes from downtown Middleburg, and surrounded by wineries and hiking trails.

4.91 out of 5 average rating, 184 reviews

Home in Upperville

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.