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A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Villas in Upperville

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    Check prices for these dates, December 14 – 15, 2026

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    Recommended hotels in Upperville

    1. Goodstone Inn & Restaurant

    A modern house with a stone facade, large windows, and a sloped roof.

    2. 18th Century Stone Cottage minutes from historic Middleburg

    A stone house with a chimney, surrounded by a well-maintained lawn and trees.

    3. DoubleTree by Hilton Front Royal Blue Ridge Shadows

    A terrace with tables set for a wedding, overlooking a golf course and a body of water.

    4. Hampton Inn Front Royal

    A Hampton Inn with a covered entrance and a parking lot.

    5. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

    A white building with a white door, two trash bins, and a small black object on the wall.

    6. L'Auberge Provencale Inn & Restaurant

    A residential area with a well-maintained garden, a lawn, and houses with distinct architectural styles.

    7. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

    A covered outdoor seating area with wicker chairs and a patterned rug, overlooking a garden and a building.

    8. TownePlace Suites by Marriott Front Royal

    A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

    9. Spacious Modern Home on Middleburg Horse Farm

    A single-story house with a porch, a front door, and two windows.

    10. Comfort Inn & Suites Winchester

    A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

    11. Microtel Inn & Suites by Wyndham Winchester

    A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

    12. Blue Mountain Cabin, secluded, perfect for couples, near main road

    A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

    13. La Quinta Inn & Suites by Wyndham Winchester

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

    14. Holiday Inn Winchester Se-Historic Gateway by IHG

    A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

    15. Spark by Hilton Winchester

    A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

    16. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

    A hot tub with a view of a forest and a sunset.

    17. TRU By Hilton Winchester

    A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

    18. Home2 Suites By Hilton Winchester

    An outdoor patio with a grill, seating, and string lights.

    19. Fairfield Inn & Suites by Marriott Winchester

    A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

    20. Super 8 by Wyndham Front Royal Near Shenandoah National Park

    A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

    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 Upperville

    Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

    See all hotels in Upperville

    A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

    Top reviews in Upperville

    Goodstone Inn & Restaurant

    A modern house with a stone facade, large windows, and a sloped roof.

    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.

    L'Auberge Provencale Inn & Restaurant

    A residential area with a well-maintained garden, a lawn, and houses with distinct architectural styles.

    Inn at Evergreen

    An outdoor patio area with multiple tables and chairs, a stone pathway, and a view of a golf course and lake.

    Hampton Inn Front Royal

    A Hampton Inn with a covered entrance and a parking lot.

    Glen Gordon Manor

    A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

    Hotel Burg

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

    La Quinta Inn & Suites by Wyndham Winchester

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

    Spark by Hilton Winchester

    A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

    TRU By Hilton Winchester

    A modern hotel building with a prominent 'TRU by Hilton' sign, multiple floors, and a parking lot in front.

    Microtel Inn & Suites by Wyndham Winchester

    A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

    Hilton Garden Inn Haymarket

    An outdoor seating area with wicker chairs and tables, large windows, and a brick building facade.

    The George Washington Hotel, A Wyndham Grand Hotel

    A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

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