Book Holiday Homes in Middleburg

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Featured Holiday Homes in Middleburg

Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub

Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub

Purcellville VA
With a stay at this vacation home in Purcellville, you'll be within a 10-minute drive of Dragon Hops and Historic Downtown Purcellville.
Opens in a new windowLuxury NEW! Woodhaven Reserve! Private Pool + Hot Tub
Beautiful 3 BR 2 Bath Private Main-first floor with AC Heat in Leesburg, VA

Beautiful 3 BR 2 Bath Private Main-first floor with AC Heat in Leesburg, VA

Leesburg VA
The price is AU$746 per night from 5 Apr to 6 Apr
AU$746
5 Apr - 6 Apr
includes taxes & fees
Located in Leesburg, this vacation home is within a 5-minute drive of Catoctin Valley and Fleetwood Farm Winery.
Opens in a new windowBeautiful 3 BR 2 Bath Private Main-first floor with AC Heat in Leesburg, VA
Modern Country House on the Shenandoah River

Modern Country House on the Shenandoah River

Charles Town WV
When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.
Opens in a new windowModern Country House on the Shenandoah River
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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$687 per night from 8 Apr to 9 Apr
AU$687
8 Apr - 9 Apr
includes taxes & 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 ...
Opens in a new windowCharming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Markham VA
With a stay at this vacation home, you'll be centrally located in Linden, within a 15-minute drive of Naked Mountain Winery & Vineyards and Aspen Dale Winery ...
Opens in a new windowBeautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
1805 Farmhouse with Heated Pool in Harpers Ferry

1805 Farmhouse with Heated Pool in Harpers Ferry

Harpers Ferry WV
Located in Harpers Ferry, this vacation home is in a rural location, within a 10-minute drive of Virginius Island and Harpers Ferry Children's Park.
Opens in a new window1805 Farmhouse with Heated Pool in Harpers Ferry
Newly Renovated Adorable Private Basement with Bathroom

Newly Renovated Adorable Private Basement with Bathroom

Herndon VA
With a stay at this vacation home in Herndon, you'll be within a 10-minute drive of Fair Oaks Mall and Reston Town Center.
Opens in a new windowNewly Renovated Adorable Private Basement with Bathroom
A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.

Leesburg VA
The price is AU$873 per night from 14 Apr to 15 Apr
AU$873
14 Apr - 15 Apr
includes taxes & fees
Located in Leesburg, this vacation home is on a river, within a 10-minute drive of Stone Tower Winery and Catoctin Valley.
Opens in a new windowA unique mountaintop getaway overlooking Willow Croft Winery.
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

bluemont VA
With a stay at this vacation home in Bluemont, you'll be in the mountains, just a 3-minute walk from Bears Den Park and 15 minutes by foot from Twin Oaks Tavern ...
Opens in a new windowBreathtaking View with an Indoor Pool
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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$176
Highest Price
AU$1,030
Popular accommodation
Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub, Beautiful 3 BR 2 Bath Private Main-first floor with AC Heat in Leesburg, VA, Modern Country House on the Shenandoah River , Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains , 1805 Farmhouse with Heated Pool in Harpers Ferry, Newly Renovated Adorable Private Basement with Bathroom , A unique mountaintop getaway overlooking Willow Croft Winery. , Breathtaking View with an Indoor Pool

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$1,030 per night from 5 Apr to 6 Apr
AU$1,030
5 Apr - 6 Apr
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
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
The price is AU$575 per night from 5 Apr to 6 Apr
AU$575
5 Apr - 6 Apr
includes taxes & fees
Located in Middleburg, this cottage is a 5-minute drive from Middleburg Community Center and 5 minutes from National Sporting Library & Museum.
Opens in a new window18th Century Stone Cottage minutes from historic Middleburg
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St Middleburg VA
The price is AU$512 per night from 5 Apr to 6 Apr
AU$512
5 Apr - 6 Apr
includes taxes & fees
A stay at The Red Fox Inn & Tavern places you in the heart of Middleburg, a 4-minute drive from Greenhill Winery & Vineyards and 7 minutes from Glenwood ...
Opens in a new windowThe Red Fox Inn & Tavern
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
2300 Dulles Corner Blvd Herndon VA
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 4 Apr to 5 Apr
AU$176
4 Apr - 5 Apr
includes taxes & fees
With a stay at Hyatt Regency Dulles International Airport in Hunter Mill, you'll be next to a golf course, within a 10-minute drive of Reston Town Center and ...
Opens in a new windowHyatt Regency Dulles International Airport
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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.