Holiday rentals in Upperville

Middleburg/Upperville-Stunning,renovated cottage

The Atoka House,a stunning 1801 log home on the historic register in Virginia hunt country.This 2-bedroom, 2.5 bath home with both upstairs and downstairs living rooms,is only 4 miles from Middleburg.Relax in the coziness of the log cabin, catch the spectacular sunsets from the deck and large fenced yard. Gas grill and outdoor firepit. Fireplace may only be used with a duraflame log(provided) for the safety of this historic home. Minutes from wineries, great meadow, polo and Upperville (UCHS)

English Cottage

MIDDLEBURG ADDRESS. Best country/Middleburg location. Five (+/-) min to town, restaurants, shopping, wedding venues. Centrally located to vineyards, breweries, horse events, more.. Guests 'LOVE' this CLEAN, tasteful, charming/Old English style - private cottage.' Bdrm w/2 twin or together as king bed. (Can separate beds.) Bath w/ rain shower. Kitchenette appointed with modern appliances. Stainless refrig., micro, toaster oven & Keurig. Dogs not left alone. 3 night min during major events.

The Cottage on Main -Virginia Wine & Horse Country

The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!

Modern Home on Middleburg Equestrian Farm

Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

WILD HARE COTTAGE king bed

Perfect for exploring wine country we are 10 minutes from Bluemont Station and Dirt Farm Brewing This property has two bedrooms King and Queen beautiful bathroom in the middle. The kitchen perfectly sized to gather four people. large sitting room out front. Sit on the front porch and watch the travelers pass by on the gravel road. Walk up to the historic Philomont store. Please note this cottage is attached to the front of the main house it’s completely separate utilites and all

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.

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.

Shenandoah Twilight - Cozy Cabin with hot tub

Escape to "Shenandoah Twilight," a cozy cabin retreat perfect for couples or small families in the heart of the Shenandoah Valley. Relax in the cozy living room with a 50" TV, electric fireplace, and plush seating. Unleash your culinary creativity in the fully equipped kitchen, and dine indoors or on the patio, where breathtaking sunsets await. Unwind in the outdoor hot tub surrounded by nature’s beauty, making this cabin the ultimate serene getaway.

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.

Littlefield Cottage

If you are looking for a super sweet and charming cottage to escape to, you've come to the right place. Live like a local in our little cottage and find out for yourself all the beauty that can be found in the country sides of Virginia. Comfortably blending modern conveniences with historic charm, the cottage sits just 1 mile outside of the quaint town of Middelburg and next door to Greenhill Winery.

The Coach Stop at White Hall

The Coach Stop offers peace and tranquility for the weary traveler wishing to experience the country life. Located on the west side of Middleburg, the tranquil location offers the country life, but with the convenience of access to Middleburg's attractions. The town of Middleburg and many attractions such as vineyards are only minutes away.