Kid-friendly vacation 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 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.

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Moonflower Cottage is a historical farmhouse nestled on two rolling acres in Virginia's wine country. Visit the area's top vineyards, dining, and antique shops. Float down the Shenandoah River. Cap your day sipping cabernet as the sun sets and the cottage blooms like the moonflowers that grow wildly. Bathe in the warm glow of string lights under the grapevine arbor or enjoy a relaxing soak in the spa. Young or old, you are sure to find the vintage that you are looking for at Moonflower Cottage.

The Big Room - Historic Schoolhouse

Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. There are even a couple sidewalks ;) We have 3 churches and a post office. The "Railside Market" serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia!

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!

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May1- Sept 14. PRIVATE 3 hours pool time daily. Plus private patio, grill and fire pit! Horses outside every window! The Cottage is located on a 230 acre horse farm. Red Gate Farm is a full-service, upscale equestrian farm, containing the Cottage, original farm house and 50 horses & ponies. Convenient to Middleburg and Purcellville, you are surrounded by mountains, wineries, breweries, and hiking, with horses right at your doorstep. All in the beautiful town of Bluemont.

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

Snickers Gap Cottage

Historic cottage nestled in the foothills of the Blue Ridge Mountains, minutes from multiple breweries, wineries, hiking and biking trails, and the Shenandoah river. At just 40 miles west of Washington DC it’s the perfect weekend getaway to the country! We are known for our miles and miles of beautiful country roads. Come spend a weekend (or more!) and get lost in Loudoun.

Creekside in Bluemont, Virginia

Creekside is located on a serene 2 acre property in the small town of Bluemont. Many wineries and breweries to visit with just a short drive, river tubing on the Shenandoah River and tons of hiking on the Appalachian Trail. 10 minutes to Purcellville to enjoy the small town, local events and great restaurants. Get ready for your weekend or week long getaway!