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Compare Vacation Homes in Middleburg with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun
Exterior

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (42)
"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
Exterior

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
Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft

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
Outdoor spa tub

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
Exterior detail

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 SAR 559
SAR 1,091 total
includes taxes & fees
3 Feb - 4 Feb
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
Gruner Bungalow

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!
Outdoor fire place and 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
Beautiful home on 4 wooded acres, front & back patios, playground & long drivewy

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
Exterior

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
Private kitchen

#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
Outdoor dining

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.
End unit with a private entrance.

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
Exterior

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
Room

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!
Soak in the tub while enjoying the beautiful view of the river below!

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is SAR 390
SAR 1,535 total
includes taxes & fees
6 Feb - 7 Feb
Terra Alta - Incredible River Views and Hot Tub!
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Firepit with quick access to house and kitchen, fridge, etc to "re-supply"

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
Living area

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
Walking Distance to Top-Rated Restaurants! 7BR w/HotTub Gazebo & Custom FirePit!
Gather for magical nights under the stars with our newly built deck and patio

Walking Distance to Top-Rated Restaurants! 7BR w/HotTub Gazebo & Custom FirePit!

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!! "
Walking Distance to Top-Rated Restaurants! 7BR w/HotTub Gazebo & Custom FirePit!
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 SAR 1,031
SAR 1,477 total
includes taxes & fees
3 Feb - 4 Feb
18th Century Stone Cottage minutes from historic Middleburg
Global Luxury Suites at Reston Town Center
Fireplace

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 SAR 472
SAR 958 total
includes taxes & fees
6 Feb - 7 Feb
Global Luxury Suites at Reston Town Center
Breathtaking views with an indoor private pool, come escape with us
Exterior

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

9.8 out of 10, Exceptional, (244)
"Our group had an amazing stay at the Bear Chase Manor! The house has great common space areas and the pool was a huge hit with everyone. We also loved the convenience of being next to the brewery along with the incredible views of nature. Can't wait to have the opportunity to stay here again!"
Breathtaking views with an indoor private pool, come escape with us
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.