Middleburg Vacation Rentals

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Vacation Rentals in Middleburg

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV

Located in Charles Town, this vacation home is on a river, within a 15-minute drive of Shenandoah River and Shannondale Springs Wildlife Management Area.

Hot Tub

Kitchen

Gruner Bungalow at Otium Cellars

Purcellville VA

Located in Purcellville, this vacation home is in a rural location, a 3-minute drive from Franklin Park and 7 minutes from Fireman's Field.

Pool

Kitchen

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Linden VA

$399 nightly

$440 total

Jan 15 - Jan 16, 2026

Total with taxes and fees

Located in Linden, this vacation home is in the mountains, within a 10-minute drive of Fox Meadow Winery and Tuckers Lane Trailhead.

Hot Tub

Kitchen

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Delaplane VA

Located in Delaplane, this vacation home is in a rural location, within a 15-minute walk of Barrel Oak Winery and Blue Valley Vineyard And Winery.

Hot Tub

Kitchen

Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Harpers Ferry WV

With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Shannondale Springs Wildlife Management Area and within a 5-minute drive of Shenandoah Lake Beach.

Hot Tub

Kitchen

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry WV

Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Bolivar Community Park.

Hot Tub

Kitchen

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Harpers Ferry WV

$385 nightly

$429 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Shannondale Springs Wildlife Management Area.

Kitchen

Washer

Cottage on King | Charming Historic Leesburg Home

Leesburg VA

$303 nightly

$349 total

Dec 18 - Dec 19

Total with taxes and fees

A stay at this vacation home places you in the heart of Leesburg, steps from Catoctin Valley and 4 minutes by foot from Earth and Fire Gallery.

Kitchen

Washer

Stone Cabin on Valley View: Fire Pit + Hot Tub

Harpers Ferry WV

$394 nightly

$417 total

Jan 14 - Jan 15, 2026

Total with taxes and fees

Located in Harpers Ferry, this vacation home is on a lake, within a 5-minute drive of Shannondale Springs Wildlife Management Area and Shenandoah River.

Hot Tub

Kitchen

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Marshall VA

$521 nightly

$558 total

Dec 18 - Dec 19

Total with taxes and fees

Located in Marshall, this vacation home is in the mountains, a 4-minute drive from Marshall Center and 5 minutes from Great Meadow.

Hot Tub

Kitchen

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

Middleburg VA

With a stay at this vacation home in Middleburg, you'll be within a 15-minute drive of Glenwood Park and Middleburg Community Center.

Washer

Dryer

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Leesburg VA

With a stay at this vacation home in Leesburg, you'll be steps from Catoctin Valley and a 2-minute drive from Tally Ho Theatre.

Hot Tub

Kitchen

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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.