Book Holiday Homes in Middleburg

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Middleburg

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

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

Bluemont
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.
Breathtaking views with an indoor private pool, come escape with us
Cozy townhome with WiFi and AC in charming Sterling

Cozy townhome with WiFi and AC in charming Sterling

Sterling
The price is AU$193 per night from 24 Dec to 25 Dec
AU$193
includes taxes & fees
24 Dec - 25 Dec
With a stay at this vacation home in Sterling, you'll be within a 15-minute drive of Reston Town Center and Seneca Square Shopping Center.
Cozy townhome with WiFi and AC in charming Sterling
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
The price is AU$1,049 per night from 26 Dec to 27 Dec
AU$1,049
includes taxes & fees
26 Dec - 27 Dec
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 ...
Terra Alta - Incredible River Views and Hot Tub!
Save an average of 15% on thousands of hotels when you're signed in
Charles Town Home w/ Private Pool & Hot Tub

Charles Town Home w/ Private Pool & Hot Tub

Charles Town
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 Locust Hill Golf Course.
Charles Town Home w/ Private Pool & Hot Tub
 Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Marshall
Located in Marshall, this vacation home is in a rural location, within a 10-minute drive of Upperville Park and National Sporting Library & Museum.
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated  Sunny Luxurious Indoor

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Middleburg
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.
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Cozy Entire Guest Suite by IAD Intl. Airport

Cozy Entire Guest Suite by IAD Intl. Airport

Herndon
The price is AU$256 per night from 26 Dec to 27 Dec
AU$256
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Herndon, you'll be within a 10-minute drive of Reston Town Center and Dulles Expo Conference Center.
Cozy Entire Guest Suite by IAD Intl. Airport
The PINK PEARL in Historic Leesburg

The PINK PEARL in Historic Leesburg

Leesburg
A stay at this vacation home places you in the heart of Leesburg, steps from Catoctin Valley and 7 minutes by foot from Raflo Park.
The PINK PEARL in Historic Leesburg
Stunning House! Minutes From Shenandoah River

Stunning House! Minutes From Shenandoah River

Harpers Ferry
Located in Harpers Ferry, this vacation home is on a lake, a 4-minute drive from Shenandoah River and 6 minutes from Shenandoah Lake Beach.
Stunning House! Minutes From Shenandoah River
Don't see what you're looking for?
See all available properties in Middleburg
View all properties
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
244 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$1,150
Popular accommodation
Breathtaking views with an indoor private pool, come escape with us, Cozy townhome with WiFi and AC in charming Sterling, Terra Alta - Incredible River Views and Hot Tub!, Charles Town Home w/ Private Pool & Hot Tub, Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor, Cozy Entire Guest Suite by IAD Intl. Airport, The PINK PEARL in Historic Leesburg, Stunning House! Minutes From Shenandoah River

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$1,150 per night from 1 Jan to 2 Jan
AU$1,150
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Middleburg, Salamander Resort And Spa is in the historical district, within a 15-minute drive of Greenhill Winery & Vineyards and Chrysalis ...
Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St, Middleburg, VA
The price is AU$592 per night from 2 Jan to 3 Jan
AU$592
includes taxes & fees
2 Jan - 3 Jan 2025
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 ...
The Red Fox Inn & Tavern
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is AU$179 per night from 5 Jan to 6 Jan
AU$179
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at Hyatt Regency Dulles in Herndon, you'll be next to a golf course, within a 15-minute drive of Reston Town Center and Dulles Expo Conference ...
Hyatt Regency Dulles
Save an average of 15% on thousands of hotels when you're signed in
Best Western Dulles Airport Inn

Best Western Dulles Airport Inn

2.5 out of 5
45440 Holiday Drive, Sterling, VA
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 25 Dec to 26 Dec
AU$138
includes taxes & fees
25 Dec - 26 Dec
When you stay at Best Western Dulles Airport Inn in Sterling, you'll be in the business district, within a 15-minute drive of Reston Town Center and Dulles Expo ...
Best Western Dulles Airport Inn
Don't see what you're looking for?
See all available properties in Middleburg
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.