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Middleburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middleburg vacation rentals

A hotel room with a bed, a dining table with chairs, a small table with a vase of flowers, and a storage unit with shelves.

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

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.6 out of 10, Exceptional, (29 reviews)
"The studio has potential but is not worth the price paid. Towels were old, mattress was soft, cobwebs were noticeable. Location is great."
United States
Kathleen
The price is ￥23,747
￥43,134 total
includes taxes & fees
Oct 12 - Oct 13
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

2. super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.6 out of 10, Exceptional, (19 reviews)
"The area was surrounded by horses, Horse farms all around, which was lovely. Very quite and peaceful. Enjoyed my time there."
United States
Lynette
The price is ￥23,685
￥46,083 total
includes taxes & fees
Oct 11 - Oct 12
super cosy cottage with high speed internet!
A stone house with a chimney, surrounded by a well-maintained lawn and trees.

3. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (67 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is ￥43,423
￥62,519 total
includes taxes & fees
Oct 12 - Oct 13
18th Century Stone Cottage minutes from historic Middleburg
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

4. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (22 reviews)
"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"
United States
Denise B.
The price is ￥48,759
￥93,846 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Modern Home on Middleburg Horse Farm
A cabin with a triangular roof, large windows, and a deck area.

5. The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views

The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
Haymarket
8.6 out of 10, Excellent, (20 reviews)
"Excellent communication, great property!"
United States
Amy E.
The price is ￥25,817
￥59,091 total
includes taxes & fees
Nov 3 - Nov 4
The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
A fenced grassy field with a clear sky and distant hills.

6. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.2 out of 10, Wonderful, (12 reviews)
"Beautiful, peaceful property. We originally lived in the area and were coming back to close out our business in town. The amenities in the home were great and everything was super clean. You definitely get the Northern Virginia rural experience here. Great location and hosts were amazing! Would stay here again!"
United States
Christina C.
The price is ￥21,317
￥42,662 total
includes taxes & fees
Oct 12 - Oct 13
Lunar Loft, with mountain views
A wooden cabin with a porch, a bench, and a table.

7. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
The price is ￥11,843
￥38,839 total
includes taxes & fees
Oct 18 - Oct 19
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A two-story house with a porch, surrounded by trees and grass.

8. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
The price is ￥29,921
￥63,687 total
includes taxes & fees
Oct 12 - Oct 13
1910 Farmhouse on 6 Acres • VA Wine Country
A spacious kitchen with a central island, a dining area with a staircase, and a view of the living room.

9. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (26 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is ￥35,528
￥62,464 total
includes taxes & fees
Oct 15 - Oct 16
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A spacious living area with a fireplace, a sofa, and a coffee table.

10. Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
Harpers Ferry
9.8 out of 10, Exceptional, (13 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is ￥17,256
￥61,534 total
includes taxes & fees
Oct 28 - Oct 29
Aslan's How - Cabin with Valley Views & Hot Tub!
A hot tub in a forested area with a rocky ground and trees.

11. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The Blue Jay | New House in the Woods w/ Hot Tub
A spacious room with a large dining table, white chairs, and a ceiling fan.

12. ~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (107 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is ￥30,317
￥62,197 total
includes taxes & fees
Oct 26 - Oct 27
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

13. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is ￥20,685
￥59,563 total
includes taxes & fees
Nov 2 - Nov 3
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A bedroom with a large bed, two bedside lamps, a potted plant, and a small ottoman.

14. Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.

Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
Sterling
9.8 out of 10, Exceptional, (120 reviews)
"We had a quick stay but it was perfect for what we needed. "
United States
Deana B.
The price is ￥12,632
￥27,001 total
includes taxes & fees
Oct 18 - Oct 19
Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
A room with a large window overlooking a forested area.

15. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is ￥18,948
￥66,159 total
includes taxes & fees
Nov 5 - Nov 6
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A covered patio area with a wooden bench, a table, and chairs.

16. Tranquil Sugarland Retreat Close to Airport/Metro

Tranquil Sugarland Retreat Close to Airport/Metro
Herndon
9.6 out of 10, Exceptional, (39 reviews)
"It was so cozy and homey! Hosts were wonderful and helpful! It was super easy going into DC by driving to the nearby metro station. Would definitely book again!"
United States
Candice H.
The price is ￥11,408
￥21,847 total
includes taxes & fees
Oct 15 - Oct 16
Tranquil Sugarland Retreat Close to Airport/Metro
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

17. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

18. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (45 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
The price is ￥33,159
￥40,929 total
includes taxes & fees
Oct 14 - Oct 15
Blue Mountain Cabin, secluded, perfect for couples, near main road
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

19. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
The price is ￥34,264
￥41,508 total
includes taxes & fees
Oct 11 - Oct 12
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A hot tub under a wooden pergola with a view of autumn trees.

20. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay "
United States
Lauren O.
The price is ￥16,464
￥65,261 total
includes taxes & fees
Oct 26 - Oct 27
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
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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Top Middleburg Hotel Reviews

Wingate by Wyndham Chantilly / Dulles Airport

Wingate by Wyndham Chantilly / Dulles Airport

8/10 Good
"Staff was great. Plenty of parking. Room was clean, needs a little upgrade."
Ulysses 7-night trip
Posted less than an hour ago
Wingate by Wyndham Chantilly / Dulles Airport

Find out more about Middleburg

Search for holiday rentals in Middleburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleburg using one of the methods below:

  • View our selection of featured holiday rentals in Middleburg
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Look no further and take a look at our great range of rental properties in Middleburg!

Frequently asked questions

Can I find vacation rentals in Middleburg?

Yes, we offer vacation rentals in Middleburg near National Sporting Library & Museum, or you can go with a more secluded option if you want a relaxing stay. The spas and restaurants are several reasons why visitors like Middleburg. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation rentals in Middleburg?

Terra Alta - Incredible River Views and Hot Tub!: This vacation home rental outside of Middleburg is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Middleburg?

Expedia has 13 vacation rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

Cultural attractions include Red Fox Fine Art and The Byrne Gallery, whereas National Sporting Library & Museum is just one of the family-friendly sights. Other places in town to visit include Middleburg Historic District and Greenhill Winery & Vineyards.

What’s a vacation rental in Middleburg like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Middleburg. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.