Cottage holiday rentals in Clarke County

Meticulous Hunt Country 2BR 1BA Upperville Cottage

Hunt & Wine Country 2BR 1BA cottage on quiet lane in the village of Upperville VA. Minutes to Upperville Colt & Horse Show, the oldest horse show in America. 1 min walk to Hunters Head English Pub & Market at Blue Water Kitchen. Convenient to wineries, foxhunting, polo, steeplechase, Middleburg (Salamander, Goodstone, Red Fox) Great Meadow, Sky Meadow. Cozy with tall ceilings. Enchanting outdoor porch w/stone FP overlooks beautifully landscaped yard w/stream. 31 miles to Dulles, 51 miles to DC.

Designer Modern Mountain Escape (w/View & Hot Tub)

Breathtaking sunsets. Stunning mountain views. Scandinavian-modern interiors. Welcome to Longview House — a modern mountain getaway designed for people who want the ✨vibes✨ of an escape to the woods, but the amenities of a boutique hotel. Steps from the Appalachian Trail, minutes from wineries/breweries, surrounded by trees that won't judge your hot tub attire. 🏡 3 chic bedrooms + two spa-inspired bathrooms 🔥 Private patio, fire pit, and hot tub 🗻 Endless spaces to relax & enjoy the view

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 Stone Cottage at Bluemont Vineyard

The cozy, stone, studio cottage is secluded in the vines & orchards of Bluemont Vineyard. ~ Spectacular sunrise views of Virginia Wine Country ~ Stone walls built from rock found on the vineyard property ~ 5 minutes to Dirt Farm Brewing, Henway Hard Cider ~ 10 minutes to local dining & shopping ~ Over 40 other vineyards to visit within an hour's drive ~ Great Appalachian Trail hiking 10 minutes away ~ River tubing on the Shenandoah 20 minutes away at Watermelon Park

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.

Quaint 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!

Cottage on Horse Farm: Wineries/Breweries, Horses!

**Pool open May 1- Sept 29 ** 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.

Bluemont Escape w/Hot Tub: Walk to AppTrail & Brew

Charming cottage that is part of a larger estate home property. Walk to Bear’s Den and the Appalachian Hiking Trails as well as popular Bear Chase Brewery. Short drive to wineries, breweries, restaurants, and river. The Cottage at Bluemont Escape is located in historic Loudoun County and includes a full kitchen, two bedrooms, and a private patio. This home sits on five acres with two other units. Enjoy the sunset from Bears Den overlook across the street, grill, or enjoy fire pit.

Quaint cottage in historical town of Paris VA!

Welcome to my home! This house was built in the 1820’s in the historical town of Paris, Virginia! With lots of history and character this house still has some of the original exposed beams and hardwood flooring! If you enjoy the outdoors, wineries, breweries, and shopping this is a perfect location for your stay! Minutes from the Appalachian trail, and Sky Meadows park there’s plenty of hiking around. Famous Ashby Inn restaurant just a short walk away and many more amazing places!

The VUE - On Top of Paradise - all inclusive!

Situated on a mountainside, the Vue blends luxury with nature. The spacious deck offers stunning mountain views, while the open-concept kitchen and living area with a grand fireplace make it feel like home. Hot tub with mountain views! With no steps at the entrance, it's designed for easy access. You'll reach The Vue via a well-maintained gravel road. 4WD or AWD is recommended from November to April, though 2WD is usually fine the rest of the year. Parking Max 4 vehicles

The Cottage at Stonecroft

Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

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.