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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.

Long Meadow Cabin: W/ Pool & Near Wineries/Hiking

Long Meadow Cabin offers a unique all-season getaway experience in the Shenandoah Valley! This beautifully constructed A-frame cabin is a wonderful place to enjoy with family & friends! Enjoy the fresh country air and pool in the warmer months and curl up to a book or movie in front of one of the two fireplaces during fall/winter. Located in the heart of Northern VA Wine Country (only 40 miles from DC) and a mere miles from Sky Meadows State Park, the options are endless for your escape.

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.

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.

Whitetail Summit - Shenandoah/hot tub/wineries

Whitetail Summit is a spacious chalet with stunning mountain views, river access, and hiking on property. You'll have close proximity to 30+ wineries/breweries, the Shenandoah National Park, the Appalachian Trail, the Shenandoah River, horseback riding, and hunting preserves. Or relax at home, with an indoor pool/ping pong table, music nook, outdoor hot tub, and fire pit. We are family/pet-friendly. REMOTE WORK: 600MBps wifi, two dedicated work-from-home spaces, and a GYM/PELOTON

Cozy Country Getaway in the Heart of Upperville

Located in the center of the historic village of Upperville - across from the Hunter's Head Tavern. House is situated on 2.5 acres of beautiful gardens. It feels like an English cottage that dates back to early 1900s and is newly updated. Tall ceilings with tons of light make this house feel very spacious. There are 2 large bedrooms with 3 beds. Upstairs is a large loft with desk area. Parking provides space for 5 vehicles. Dogs are welcome! Wifi available.

The Nook: Cabin, wood stove, outdoor dome

Welcome to The Nook, a cabin nestled into the ridges surrounding Front Royal. The cozy retreat sleeps four! Enjoy evenings spent watching the sunset through the trees while on the wrap-around deck, or hang in the geodome as night closes in around you! We hope that you take the time to explore the towns, trails, vineyards, orchards, and river around you before meandering back to relax in your nook with a fire, a book, and a vinyl record playing in the background.

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

Escape to this cozy 2BR/2BA cabin in Front Royal, VA! Relax in the private hot tub on the screened-in porch, unwind in the stylish open-concept living space, or enjoy the peaceful surroundings from the spacious deck. The king suite and twin bedroom with a desk make it perfect for couples, families, or remote work. Conveniently located near scenic hiking trails and local wineries, this is your perfect nature retreat. Book now for a relaxing or romantic getaway!