
House vacation rentals in Middleburg
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Top-rated house rentals in Middleburg
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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)

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.

Clean 5BR w Heated Pool, Spa - Horse, Wine Country
Escape the city to this spacious 5BR / 3.5BA home with a heated pool and spa on 8 acres in the heart of Northern Virginia's Horse and Wine country. The house is professionally designed for large groups of adults and kids for family vacations, reunions, and retreats. 2 miles from the one-stop-light town of Marshall with nationally recognized restaurants, bakeries. And in the heart of Virginia's Horse & Wine country - 7 wineries, equestrian facilities/shows, and state park within 15 minutes.

Virginia Wine Country Retreat 60 mi. from DC
Quiet and serene, this Wine Country Retreat in Fauquier County is an easy 60 mile drive from DC. Enjoy privacy and natural beauty in a 4-BR, 6,000 SF home on 11+ acres, with gorgeous views of the foothills of the Blue Ridge Mountains. Lovely antiques and modern amenities, WiFi, washer/dryer, gourmet kitchen. 1st floor BR, 3 more upstairs. Large deck for cookouts or stargazing! Perfect for groups doing winery tours, a "girls get-away" weekend, family gatherings, corporate retreats.

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.

Whole House -Seven Elms Farm B&B
Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

Restored 1820 Waterford Village Farmhouse
We restored this 1820 village farmhouse in 2016. It is situated in the heart of the historic village of Waterford. It has 2 1/2 acres behind, with two barns, a herd of very friendly goats, chickens, and vegetable, herb and flower gardens. The house backs up to The Phillips Farm, 150 acres of preserved land and public walking trails. Beautiful sunset views from the back porch. The house, a work in progress, was featured in both Country Living and Preservation Magazines.

Downtown Leesburg Cottage. Walk to everything!
Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

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.

King Bed 3 Bedroom New House
New modern farmhouse in a private, wooded, but centrally located area where the entire family or several couples can escape for an enjoyable weekend near the acclaimed Virginia Wine Country. Paved parking and super fast WiFi. Minutes from some of the best local Vineyards, Wineries and Breweries. Twenty minutes from downtown Leesburg, historic Middleburg, all less than an hour from Washington DC.

Historic Tip of the Hill, Purcellville, Virginia
Historic Tip of the Hill, ca 1762, is located just a 1/2 mile outside of the town of Purcellville, VA. Close to all the major wedding venues. Restaurants, wine tasting, breweries, live music, the AT, Shenandoah River, W,O&D bike trail & more are just minutes away. This 18th century home has been completely updated but with its charm and character intact. 3 BR, 1.5 BA, sleeps up to 6.
Popular amenities for Middleburg house rentals
House rentals with a pool

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

Cedar Creek Wayside Castle

Middleburg country home

An Escape Bordering National Park land 1 mi to C&O

Walnut Lane

Indoor Heated Pool~EV- Arcade~Fire Pit-WIFI-VIEWS!
Weekly house rentals

Historic Farmhouse, Fully Renovated in Fall 2023

The Garden House

Historic country retreat, a piece of quiet heaven.

Historic Bluemont Farmhouse

English Cottage/Main House

Skyline Villa-Views, Wineries, Hot Tub, Nat’l Park

Peaceful, Authentic Stone Cottage with Cozy Charm

Atoka Cottage
Private house rentals

Woodhaven Reserve | Private Pool + Hot Tub!

River House

Gorgeous cabin on Blue Ridge

Wine Country, Hikes & Dogs!

It's Own Destination/Farm Cottage with Mtn. Views

The Upperville Academy

The Old Stonehouse - Walking trails & creek

Touch of Tuscan - Minutes to Wine, Beer, Hiking
Quick stats about house rentals in Middleburg

Nightly prices starting at
Middleburg vacation rentals start at ﺩ.ﺇ2,828 per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middleburg rentals

5 Average rating
Middleburg stays are highly rated by guests—averaging 5 out of 5!
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Luray Caverns
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Howard University
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