Book Holiday Homes in Middleburg

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Featured Holiday Homes in Middleburg

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV
The price is AU$611 per night from 8 Jan to 9 Jan
AU$611
8 Jan - 9 Jan 2026
includes taxes & fees
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.
Opens in a new windowTerra Alta - Incredible River Views and Hot Tub!
Gruner Bungalow at Otium Cellars

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.
Opens in a new windowGruner Bungalow at Otium Cellars
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

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

Linden VA
The price is AU$609 per night from 20 Jan to 21 Jan
AU$609
20 Jan - 21 Jan 2026
includes taxes & fees
Located in Linden, this vacation home is in the mountains, within a 10-minute drive of Fox Meadow Winery and Tuckers Lane Trailhead.
Opens in a new window🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
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Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

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.
Opens in a new windowPets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

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 ...
Opens in a new windowCozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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.
Opens in a new windowLarge Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

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

Harpers Ferry WV
The price is AU$720 per night from 28 Dec to 29 Dec
AU$720
28 Dec - 29 Dec
includes taxes & 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 ...
Opens in a new windowCharming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home

Leesburg VA
The price is AU$525 per night from 5 Jan to 6 Jan
AU$525
5 Jan - 6 Jan 2026
includes taxes & 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.
Opens in a new windowCottage on King | Charming Historic Leesburg Home
Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub

Harpers Ferry WV
The price is AU$625 per night from 14 Jan to 15 Jan
AU$625
14 Jan - 15 Jan 2026
includes taxes & 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.
Opens in a new windowStone Cabin on Valley View: Fire Pit + Hot Tub
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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.

Middleburg Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middleburg vacation homes are the perfect way for you to wing it.

Holiday houses in Middleburg let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middleburg in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middleburg adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middleburg with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middleburg vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middleburg Holiday Homes essential information

Accommodation
281 Holiday Homes
Lowest Price
AU$159
Highest Price
AU$945
Popular accommodation
Terra Alta - Incredible River Views and Hot Tub!, Gruner Bungalow at Otium Cellars, 🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries, Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery, Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Cottage on King | Charming Historic Leesburg Home, Stone Cabin on Valley View: Fire Pit + Hot Tub

Top trending hotels in Middleburg

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is AU$945 per night from 21 Jan to 22 Jan
AU$945
21 Jan - 22 Jan 2026
includes taxes & fees
Located in Middleburg, Salamander Resort And Spa is in the historical district, within a 15-minute drive of Greenhill Winery & Vineyards and Chrysalis ...
Opens in a new windowSalamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
A stay at The Red Fox Inn & Tavern places you in the heart of Middleburg, a 4-minute drive from Greenhill Winery & Vineyards and 9 minutes from Aldie Mill Historic ...
Opens in a new windowThe Red Fox Inn & Tavern
HYATT house Sterling/Dulles Airport-North

HYATT house Sterling/Dulles Airport-North

3 out of 5
45520 Dulles Plz Sterling VA
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 28 Dec to 29 Dec
AU$159
28 Dec - 29 Dec
includes taxes & fees
When you stay at HYATT house Sterling/Dulles Airport-North in Sterling, you'll be near the airport, within a 5-minute drive of Herndon Centennial Golf Course ...
Opens in a new windowHYATT house Sterling/Dulles Airport-North
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 25 Dec to 26 Dec
AU$170
25 Dec - 26 Dec
includes taxes & fees
Located in Herndon, Hyatt Place Herndon Dulles Airport East is within a 10-minute drive of Reston National Golf Course and Reston Town Center.
Opens in a new windowHyatt Place Herndon Dulles Airport East
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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.

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^Subject to availability and chosen travel dates.