Middleburg Cottages

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Cottages in Middleburg

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hamilton VA

$347 nightly

$396 total

Jun 25 - Jun 26

Total with taxes and fees

With a stay at this cottage in Hamilton, you'll be just steps from Catoctin Valley and Hunters Run Wine Tasting Barn.

Pool

Hot Tub

Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Purcellville VA

With a stay at this cottage in Purcellville, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Harpers Ferry National Historical Park.

Pool

Kitchen

Hunt Country cottage in Upperville!

Upperville VA

Located in Upperville, this cottage is a 2-minute drive from Upperville Park and 7 minutes from Paris Barns.

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA

$369 nightly

$396 total

Jul 2 - Jul 3

Total with taxes and fees

Located in Middleburg, this cottage is a 5-minute drive from Middleburg Community Center and 5 minutes from National Sporting Library & Museum.

Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry WV

$415 nightly

$462 total

Jul 1 - Jul 2

Total with taxes and fees

Located in Harpers Ferry, this cottage is in the mountains, within a 10-minute drive of Shannondale Springs Wildlife Management Area and Shenandoah Lake Beach.

Hot Tub

Kitchen

Historical cottage in the town of Paris

Paris VA

Located in Paris, this cottage is on a river, within a 5-minute drive of Paris Barns and Sky Meadows State Park.

Historic Schoolhouse on Winery Row

Purcellville VA

With a stay at this cottage in Purcellville, you'll be on the waterfront, within a 15-minute drive of Harpers Ferry National Historical Park and Sweet Run State Park.

Kitchen

Washer

Littlefield Cottage

Middleburg VA

With a stay at this cottage in Middleburg, you'll be within a 5-minute drive of Greenhill Winery & Vineyards and Middleburg Historic District.

A Restored Wagon Barn On A 1790's Farm.

Purcellville VA

Located in Purcellville, this cottage is in the mountains, within a 10-minute drive of K & S Pewter and Doukenie Winery.

Breakfast included

Kitchen

Charming 3-bedroom cottage in farm & wine country

Berryville VA

When you stay at this cottage in Berryville, you'll be within a 10-minute drive of Barns of Rose Hill and Mackintosh Fruit Farm.

Kitchen

Washer

The VUE • Mountaintop 4BR • Hot Tub & Views

Front Royal VA

$585 nightly

$645 total

Jul 5 - Jul 6

Total with taxes and fees

Located in Front Royal, this cottage is a 5-minute drive from Shenandoah River and 7 minutes from John T Shipe JR Park.

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

Waterford VA

Located in Waterford, this cottage is within a 15-minute drive of Village Winery and Hunters Run Wine Tasting Barn.

Kitchen

Washer

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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.