Middleburg Vacation Rentals

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Vacation Rentals in Middleburg

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV

$361 nightly

$402 total

Dec 22 - Dec 23

Total with taxes and fees

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.

Hot Tub

Kitchen

Aeris Suite

Sterling VA

$175 nightly

$200 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Sterling, you'll be within a 10-minute drive of Herndon Centennial Golf Course and Center for Innovative Technology Complex.

Kitchen

Washer

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

$364 nightly

$401 total

Jan 13 - Jan 14, 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

With a stay at this vacation home in Harpers Ferry, you'll be in the mountains, within a 10-minute drive of Hollywood Casino at Charles Town Races and Shenandoah River.

Hot Tub

Kitchen

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

Harpers Ferry WV

$385 nightly

$429 total

Dec 14 - Dec 15

Total with taxes and fees

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

Kitchen

Washer

Cottage on King | Charming Historic Leesburg Home

Leesburg VA

$332 nightly

$382 total

Jan 5 - Jan 6, 2026

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 Tally Ho Theatre.

Kitchen

Washer

Stone Cabin on Valley View: Fire Pit + Hot Tub

Harpers Ferry WV

$389 nightly

$411 total

Dec 15 - Dec 16

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

$483 nightly

$517 total

Dec 15 - Dec 16

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

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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.