Book Holiday Homes in Middleburg

Start date: Check-in selected.
To Date
End date: Check-out

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

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
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

Aeris Suite

Aeris Suite

Sterling
The price is AU$311 per night from 6 Nov to 7 Nov
AU$311
6 Nov - 7 Nov
includes taxes & fees
With a stay at this vacation home in Sterling, you'll be within a 15-minute drive of Reston Town Center and Dulles Expo Conference Center.
Opens in a new window Aeris Suite
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

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

Leesburg
The price is AU$589 per night from 6 Nov to 7 Nov
AU$589
6 Nov - 7 Nov
includes taxes & fees
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.
Opens in a new windowCozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Save an average of 15% on thousands of hotels when you're signed in
The Apple Mountain House

The Apple Mountain House

Front Royal
The price is AU$756 per night from 6 Nov to 7 Nov
AU$756
6 Nov - 7 Nov
includes taxes & fees
Located in Front Royal, this vacation home is on a river, a 5-minute drive from Shenandoah River and 7 minutes from John T Shipe JR Park.
Opens in a new windowThe Apple Mountain House
New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After

New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After

Chantilly
With a stay at this vacation home in Chantilly, you'll be a 3-minute drive from Dulles Expo Conference Center and 7 minutes from Fair Oaks Mall.
Opens in a new windowNew Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After
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
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
Gruner Bungalow at Otium Cellars

Gruner Bungalow at Otium Cellars

Purcellville
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
A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Harpers Ferry, WV
The price is AU$602 per night from 10 Nov to 11 Nov
AU$602
10 Nov - 11 Nov
includes taxes & fees
With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Virginius Island.
Opens in a new windowA peaceful, forest retreat with stunning views near historic Harpers Ferry.
Newly Renovated Adorable Private Basement with Bathroom

Newly Renovated Adorable Private Basement with Bathroom

Herndon
The price is AU$249 per night from 15 Nov to 16 Nov
AU$249
15 Nov - 16 Nov
includes taxes & fees
With a stay at this vacation home in Herndon, you'll be within a 10-minute drive of Dulles Expo Conference Center and Fair Oaks Mall.
Opens in a new windowNewly Renovated Adorable Private Basement with Bathroom
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
304 Holiday Homes
Lowest Price
AU$172
Highest Price
AU$1,399
Popular accommodation
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Aeris Suite, Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!, The Apple Mountain House, New Luxury 3 BEDR, Entertainment Kitchen, Work from Home, Sought After, Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people, Gruner Bungalow at Otium Cellars, A peaceful, forest retreat with stunning views near historic Harpers Ferry., Newly Renovated Adorable Private Basement with Bathroom

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$1,039 per night from 16 Nov to 17 Nov
AU$1,039
16 Nov - 17 Nov
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
The price is AU$1,399 per night from 8 Nov to 9 Nov
AU$1,399
8 Nov - 9 Nov
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 9 minutes from Aldie Mill Historic ...
Opens in a new windowThe Red Fox Inn & Tavern
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$178 per night from 16 Nov to 17 Nov
AU$178
16 Nov - 17 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is AU$172 per night from 23 Nov to 24 Nov
AU$172
23 Nov - 24 Nov
includes taxes & fees
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 ...
Opens in a new windowHyatt Regency Dulles
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.