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A vineyard with rows of grapevines under a clear sky.

Photo by Stephanie Sutton

Middleburg Vacation Rentals

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    Check prices for these dates, December 13–14, 2026

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    Our top choices for Middleburg vacation homes

    1. super cosy cottage with high speed internet!

    A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

    2. Spacious Modern Home on Middleburg Horse Farm

    A covered porch with stone flooring, two chairs, a rug, and a glass door with a black frame.

    3. Hunters Retreat with High Speed Internet

    covered patio

    4. 1910 Farmhouse on 6 Acres • VA Wine Country

    A covered porch with an American flag, a view of a green lawn, and a pathway.

    5. Leesburg Hideaway- King Bed + Private Backyard

    A room with a desk, chair, television, and a large sliding glass door leading to an outdoor area with a wooden deck and a white fence.

    6. Cozy 2-bedroom house with charming views and golf course.

    A bedroom with a bed, two nightstands, a rug, and a door.

    7. Historic Downtown Home with Fire Pit

    A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a window providing natural light.

    8. Retreat in Historic Downtown Leesburg - Walkable to Everything!

    A room with a door leading to a balcony, a mirror on the wall, and a welcome mat at the entrance.

    9. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

    A beach with two empty lounge chairs facing a calm lake, surrounded by a chain-link fence and a dock in the background.

    10. Downtown Retreat with 2 Primary Suites

    Front hallway and staircase to the two upstairs suites

    11. Still Meadow Farm

    Still Meadow Farm (1)

    12. Downtown Cottage with Fire Pit

    A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

    13. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

    A deck with outdoor seating, a fire pit, and a view of trees.

    14. Stylish Studio with Kitchenette

    A bathroom with a white sink, a mirror, and a toilet. There is a door leading to a hallway with a staircase and a shelf unit with various items.

    15. Charming Cottage, Walk to Downtown, Porch Swings

    A fire pit surrounded by Adirondack chairs, a covered grill, and a stone wall with logs.

    16. Mountain Views w/Hot Tub, 95” TV & Trail Access

    A vineyard with rows of grapevines, a wooden building with a balcony, and a paved path.

    17. Renovated 3B/3B Home | Downtown | Private Fire Pit

    A kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

    18. Storybook cottage on Leesburg's most historic block — walk to everything

    A large estate with multiple buildings, expansive outdoor seating areas, and surrounding vineyards.

    19. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

    A large, modern house with a balcony, surrounded by a forest and rocky terrain.

    20. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

    An outdoor deck with wicker furniture, a table, and chairs.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Middleburg

    Nestled in Virginia's horse country, this charming town invites you to explore historic inns and boutique wineries. Saddle up for a guided trail ride or join a polo match, then unwind at a cozy tavern with locally-sourced fare.

    See all hotels in Middleburg

    A vineyard with rows of grapevines under a clear sky.

    Photo by Stephanie Sutton

    Top reviews in Middleburg

    Hotel Burg

    A hotel with a brick facade, multiple windows, and a well-lit entrance.

    Home2 Suites by Hilton Charles Town

    A hotel with a prominent "HOME" sign, outdoor seating area, and a covered entrance.

    Salamander Middleburg

    A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.

    Hampton Inn & Suites Herndon-Reston

    A modern hotel lobby with a bar, seating area, and a large TV screen.

    Residence Inn by Marriott Chantilly Dulles South

    A buffet setup with various food items and drinks, a fireplace, and seating arrangements in a dining area.

    Hampton Inn & Suites Charles Town

    A spacious hotel lobby with multiple seating areas, a long communal table, and large windows offering views.

    Fairfield Inn & Suites by Marriott at Dulles Airport

    A modern living room with a sofa, armchairs, a coffee table, a fireplace, and a television.

    Washington Dulles Marriott Suites

    A multi-story hotel with a modern design, featuring a prominent entrance with a covered area and a parking lot in front.

    Hampton Inn Manassas

    A modern hotel lobby with a dining area, a flat-screen TV, and a coffee station.

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