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 NZ$695 per night from 8 Jan to 9 Jan
NZ$695
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this family-friendly holiday home in Charles Town. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Hollywood Casino at Charles Town ...
Opens in a new windowTerra Alta - Incredible River Views and Hot Tub!
Gruner Bungalow at Otium Cellars

Gruner Bungalow at Otium Cellars

Purcellville VA
Stay at this family-friendly holiday home in Purcellville. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the helpful staff and the property ...
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 NZ$693 per night from 20 Jan to 21 Jan
NZ$693
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this holiday home in Linden. Enjoy free Wi-Fi, a garden and patios. Popular attractions Tuckers Lane Trailhead and Fox Meadow Winery are located ...
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
Stay at this family-friendly holiday home in Delaplane. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions 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
Stay at this holiday home in Harpers Ferry. Enjoy a garden, laundry facilities and patios. Popular attractions Shannondale Springs Wildlife Management Area and ...
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
Stay at this holiday home in Harpers Ferry. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hollywood Casino at Charles Town Races and ...
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 NZ$818 per night from 28 Dec to 29 Dec
NZ$818
28 Dec - 29 Dec
includes taxes & fees
Stay at this family-friendly holiday home in Harpers Ferry. Enjoy a water park, laundry facilities and a pool table. Popular attractions Hollywood Casino at ...
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 NZ$598 per night from 5 Jan to 6 Jan
NZ$598
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this family-friendly holiday home in Leesburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tally Ho Theatre and Loudoun Museum ...
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 NZ$711 per night from 14 Jan to 15 Jan
NZ$711
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this family-friendly holiday home in Harpers Ferry. Enjoy a garden, laundry facilities and balconies. Popular attractions Shenandoah Lake Beach and Shannondale ...
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
NZ$199
Highest Price
NZ$1,084
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 NZ$1,084 per night from 21 Jan to 22 Jan
NZ$1,084
21 Jan - 22 Jan 2026
includes taxes & fees
Stay at this luxury resort in Middleburg. Enjoy free Wi-Fi, an outdoor pool and a full-service spa. Popular attractions Middleburg Community Center and Red Fox ...
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
Stay at this inn in Middleburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 NZ$200 per night from 26 Dec to 27 Dec
NZ$200
26 Dec - 27 Dec
includes taxes & fees
Stay at this business-friendly hotel in Sterling. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
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 NZ$199 per night from 23 Jan to 24 Jan
NZ$199
23 Jan - 24 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Herndon. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the helpful ...
Opens in a new windowHyatt Place Herndon Dulles Airport East
Don't see what you're looking for?
See all available properties in Middleburg
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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.

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