Photo by Stephanie Sutton

Middleburg Vacation Rentals

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Middleburg Vacation Homes

Trailside Retreat in breathtaking Western Loudoun
Outdoor dining

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (41)
"Large house, good for a big group. Well equipped. Accommodated our need for an early check-in."
Trailside Retreat in breathtaking Western Loudoun
Charming 4-bedroom townhome 8 min to Airport 30 minutes to DC Pet friendly
Fridge, microwave, oven, stovetop

Charming 4-bedroom townhome 8 min to Airport 30 minutes to DC Pet friendly

7.0 out of 10, Good, (2)
"A great laid out townhome property that comfortably slept six adults. Well situated in northern Virginia and Loudon County, directly across a hidden gem in Claude Moore Park and Rec Center. A new offering that has wonderful potential, but needs a thorough, professional cleaning and some repairs."
Charming 4-bedroom townhome 8 min to Airport 30 minutes to DC Pet friendly
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Fridge, microwave, oven, stovetop

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (32)
"We had a lovely weekend snowed in at this beautiful mountain home. With help from the hosts and kind neighbors, we were able to get home safely after a big snow storm, and def recommend 4 wheel drive for those going in winter! Will definitely return!"
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (48)
"Is there traffic/road noise? Yes. Can you walk to everything on King St? Also yes. Tradeoffs."
The price is CA $215
CA $419 total
includes taxes & fees
Feb 3 - Feb 4
Cottage on King | Charming Historic Leesburg Home
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Dining

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (22)
"Our group of seven was very, very comfortable there. It was nice to have two separate living areas one on the upper floor and one on the lower floor where one area could be the quieter area and the other area could be the louder area. Bedrooms were separate from the main living spaces on both the first floor and the basement which was very nice. Price per value was excellent, and whenever I return to the area, I will happily stay there again if it’s available!"
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Gruner Bungalow at Otium Cellars
Smart TV, fireplace, table tennis, books

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (93)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
Terrace/patio

1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!

10.0 out of 10, Exceptional, (46)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Outdoor dining

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

9.8 out of 10, Exceptional, (51)
"We enjoyed the house overall. There was some draining issues in one of the restrooms but nothing too bad. Definitely wish there were more TVs in the guest rooms. Other than that the house worked well for our family of 8. "
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
The PINK PEARL in Historic Leesburg
Outdoor dining

The PINK PEARL in Historic Leesburg

9.6 out of 10, Exceptional, (31)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Property grounds

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

8.4 out of 10, Very good, (5)
"Good experience. Well maintained. Very clean. Several nice detail extras. "
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Fridge, microwave, oven, stovetop

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (96)
"Good time was had by all."
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Luxurious home with golf course view, deck, grill, Peloton! King size bed.
Interior

Luxurious home with golf course view, deck, grill, Peloton! King size bed.

9.8 out of 10, Exceptional, (34)
"It was great."
Luxurious home with golf course view, deck, grill, Peloton! King size bed.
Luxury Home. Hot-tub, close to IAD & Hylton PAC.
Outdoor spa tub

Luxury Home. Hot-tub, close to IAD & Hylton PAC.

Luxury Home. Hot-tub, close to IAD & Hylton PAC.
Cozy Country Getaway in the Heart of Upperville
Smart TV

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (7)
"Highly recommend this place."
Cozy Country Getaway in the Heart of Upperville
Romantic Stone Cottage Circa 1869-75 acres to Hike
1 bedroom, WiFi, bed sheets

Romantic Stone Cottage Circa 1869-75 acres to Hike

9.2 out of 10, Wonderful, (5)
"Unfortunately we happened to stay when there was a wind storm in the county so we lost power, water and heat for the night. We texted the host to check on candles and/or flashlights but were told to “just use our phones”. (Not really an option when you’ve been traveling all day and phones are almost dead). The cottage is very rustic and not quite as comfortable as the pictures make it out to be. The bed is extremely firm so be aware if you have bad hips or back. There’s also glade plug ins in...
Romantic Stone Cottage Circa 1869-75 acres to Hike
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is CA $158
CA $602 total
includes taxes & fees
Feb 6 - Feb 7
Terra Alta - Incredible River Views and Hot Tub!
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Fridge, microwave, oven, stovetop

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

10.0 out of 10, Exceptional, (10)
"First time using a rental service and Karen and Todd made it super easy. They were communicative before, during, and even after our stay. The house easily accommodated the 8 people in my party. "
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
Outdoor dining

Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

10.0 out of 10, Exceptional, (12)
"Good location. Excellent amenities. Inside and outside! Exactly as advertised. The large farmhouse dining table was perfect for everyone to enjoy meals & play card games together! A Great place for our Family gathering to start the New Year!! "
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
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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Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (35)
"We absolutely loved this little cottage. It's a great location near Middleburg, tucked back in the woods. It's got everything you need for a peaceful retreat. A perfect place to curl up in front of the fire with a book. The host was so welcoming and easy to work with. We'll definitely be back!"
The price is CA $396
CA $572 total
includes taxes & fees
Feb 2 - Feb 3
18th Century Stone Cottage minutes from historic Middleburg
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Desk, iron/ironing board, free WiFi, bed sheets

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

9.8 out of 10, Exceptional, (13)
"lovely room, great shower, so wuiet and peaceful, great environs (sheep! donkey! cheese!), such a nice stay!"
The price is CA $216
CA $392 total
includes taxes & fees
Feb 2 - Feb 3
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Global Luxury Suites at Reston Town Center
Reception

Global Luxury Suites at Reston Town Center

3.5 star property
8.2 out of 10, Very good, (122)
"The location, the building and the property manager, Bushra, were excellent. Lots of local businesses are walkable and a great Reston Town Center location. "
The price is CA $190
CA $378 total
includes taxes & fees
Feb 1 - Feb 2
Global Luxury Suites at Reston Town Center
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.