Holiday rentals in Upperville

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Top-rated holiday rentals in Upperville

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Top guest favourite

The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.

Guest house in Middleburg

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

5.0 out of 5 average rating, 143 reviews

Top guest favourite

An open-concept kitchen and dining area features modern appliances and a spacious island countertop. A large dining table is surrounded by sleek chairs. Natural light pours in through multiple windows, highlighting the warm wood floors and neutral color palette.

Home in Middleburg

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.

4.96 out of 5 average rating, 220 reviews

Guest favourite

A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.

Cottage in Marshall

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. Please be mindful this property is near a train track, charming!

4.9 out of 5 average rating, 143 reviews

Guest favourite

A country-style home with a yellow facade and a green metal roof is set against a clear blue sky. A welcoming front porch features a decorative flag, surrounded by well-kept greenery. The stone pathway invites visitors toward the entrance.

Home in Upperville

Reynard's Retreat in Upperville

The perfect hunt box in Upperville and central to all things horses, hunting and wine country. 3BR 2BA home on a country road in the village of Upperville within an hour to DC and only a half mile to Upperville Colt & Horse Showgrounds. Great Meadows, home to horse shows, steeplechase races, and polo…only minutes away. For our non-horsey friends, the house sits is the center of Northern Virginia’s wine country, surrounded by multiple of the region’s best-known vineyards and Sky Meadows.

4.95 out of 5 average rating, 22 reviews

Guest favourite

An aerial view captures a vibrant organic vegetable garden surrounded by a black wooden fence. The garden features neatly arranged raised beds filled with various plants, along with gravel pathways. A shaded seating area is visible, alongside a shed and open green space beyond.

Guest house in Middleburg

Fox Hill Barn Guest Cottage Retreat

Enjoy the lovely setting of this romantic spot in nature, just minutes from the historic charm of Middleburg. Set on a tranquil horse property, this cottage offers a serene retreat amidst rolling pastures and breathtaking views. Whether you're a nature enthusiast, equestrian, remote worker, or seeking a romantic getaway, this is your ideal destination. Enjoy nearby wineries, breweries, scenic trails, and the delightful town of Middleburg—only 3 minutes away. Life is too short. Enjoy!

4.95 out of 5 average rating, 104 reviews

Top guest favourite

A charming cottage features a standing seam metal roof and clapboard-style siding. The cozy front porch is adorned with rocking chairs and hanging flower baskets. Lush greenery surrounds the stone pathway leading up to the inviting front door.

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.

4.91 out of 5 average rating, 210 reviews

Top guest favourite

Home in Upperville

Horse Country | Pool | MNT Views | Full Kitchen

Welcome to Serenity Manor, the perfect getaway for large families or groups of friends looking to make memories together! This 4200 sq. ft. home boasts a private pool, 6 bedrooms, 6.5 baths, a pool house with games, and a private courtyard garden with plenty of places to enjoy coffee, read, and relax outdoors. Conveniently Located to: 3 Minute Drive to Upperville Horse Show 5 Min Drive to The Oaks Garden 10 Min Drive To Middleburg 5 Min Drive to Slaters Run Vineyard

4.92 out of 5 average rating, 26 reviews

Top guest favourite

Barn in Middleburg

Middleburg Carriage House

Hunt Country charm with modern design and amenities. The rebuilt carriage house overlooks adjacent vineyard and Blue Ridge Mountains. The interior showcases reclaimed materials and wood from the original dwelling. The large flagstone patio offers rolling mountain views where you can enjoy your morning coffee or glass of local wine after a day of winery visits. A two minute drive to historic downtown Middleburg; next to wineries and polo. Enjoy your next getaway!

4.93 out of 5 average rating, 231 reviews

Top guest favourite

The charming exterior features a light-colored house with a metal roof, framed by well-kept greenery. A bold blue door provides an inviting entrance, while white window shutters accentuate the classic style of the home.

Cottage in Upperville

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.

4.9 out of 5 average rating, 111 reviews

Top guest favourite

A modern kitchen and living area are showcased, featuring a large central island with seating for six. Two prominent horse portraits hang above the island, while the sleek design is complemented by gold accents and a mix of light and dark tones throughout the space.

Barn in Middleburg

The Studio

🐞1 mile from the center of Middleburg, this gem allows you to enjoy the beauty of a gorgeous Middleburg Farm when you stay in this unique tractor barn turned high end luxury studio apartment! This is for the customer who wants to experience country living but does not want to give up any luxury 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property.

4.98 out of 5 average rating, 114 reviews

Guest favourite

A wooden walking bridge connects to a secluded cabin situated on an island, surrounded by lush greenery and a calm lake. Gentle hills rise in the background, providing a scenic view of the countryside.

Cabin in Upperville

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.

4.94 out of 5 average rating, 187 reviews

Top guest favourite

A blue sign reads 'Green Acre', supported by a wooden post beside a paved road. The background features a grassy landscape with horses grazing in a fenced area. Lush trees and hills are visible in the distance under soft, natural lighting.

Cottage in Upperville

Green Acre - A Hunt Country Retreat

Charming 2100 sq ft cottage on 1 acre. Fully fenced for dogs when the gate is closed. Walk to Hunters Head tavern, historic Trinity Church. Close to Lost Mountain winery, Sky Meadows State Park, Ashby Inn. Scenic 10 minute drive to the shops and sights of Middleburg and the Salamander Resort. 15 minutes to restaurants and shops of Marshall. AMENITIES: Full Kitchen *Nespresso * Gas Fireplace *Daybed in Alcove *Wi-Fi *cellular signal extender

4.95 out of 5 average rating, 40 reviews