Middleburg Vacation Rentals

Name: Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Address: Leesburg

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Vacation Rentals in Middleburg

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Located in Purcellville, this vacation home is within a 5-minute drive of Fireman's Field and Purcellville Skating Rink.

Pet-Friendly Berryville Home: Walk to Main Street!

With a stay at this vacation home in Berryville, you'll be a 5-minute walk from The Fire House Gallery and 5 minutes by foot from Barns of Rose Hill.

NEW LISTING! Mountain Chic Retreat by RedAwning

Free Cancellation

Located in Harpers Ferry, this vacation home is in the mountains, within a 15-minute drive of Shenandoah Lake Beach and Shenandoah River.

Breathtaking views with an indoor private pool, come escape with us

Located in Bluemont, this vacation home is in the mountains, a 3-minute drive from Twin Oaks Tavern Winery and 6 minutes from Hill High Country Store.

New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After

$502

includes taxes & fees

$473 per night

Nov 17 - Nov 18

With a stay at this vacation home in Chantilly, you'll be a 3-minute drive from Dulles Expo Conference Center and 7 minutes from Fair Oaks Mall.

Mountain Getaway - 7 beds (2 King) - Large Common Area

Located in Harpers Ferry, this vacation home is in the mountains, a 5-minute drive from Shenandoah River and 6 minutes from Shenandoah Lake Beach.

Charles Town Townhome: 9 Mi to Harpers Ferry

With a stay at this vacation home in Charles Town, you'll be within a 10-minute drive of Hollywood Casino at Charles Town Races and Jefferson County Courthouse.

Terra Alta - Incredible River Views and Hot Tub!

$480

includes taxes & fees

$434 per night

Nov 7 - Nov 8

With a stay at this vacation home in Charles Town, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and Shenandoah River.

Modern Country House on the Shenandoah River

When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.

Hot Tub, Poker Table, River Access & Kayaks and Wineries

When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Located in Middleburg, this vacation home is in a rural location, a 5-minute drive from Greenhill Winery & Vineyards and 5 minutes from Red Fox Fine Art.

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

Located in Leesburg, this vacation home is in a rural location, a 3-minute drive from Catoctin Valley and 5 minutes from Fleetwood Farm Winery.

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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.