A sunrise over a mountainous landscape with layers of clouds.

Middleburg Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middleburg vacation rentals

Exterior

1. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is AED 1,010
AED 1,372 total
includes taxes & fees
30 Sep - 1 Oct
18th Century Stone Cottage minutes from historic Middleburg
Coffee/tea maker, fridge, microwave, oven

2. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (21 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 AED 1,153
AED 2,077 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Modern Home on Middleburg Horse Farm
Desk, iron/ironing board, WiFi (free), bed sheets

3. 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 AED 551
AED 963 total
includes taxes & fees
29 Sep - 30 Sep
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Exterior

4. 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 AED 681
AED 1,365 total
includes taxes & fees
21 Oct - 22 Oct
The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
Coffee/tea maker, fridge, microwave, oven

5. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres
Loudoun County
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
The price is AED 826
AED 1,594 total
includes taxes & fees
28 Sep - 29 Sep
DC Wine Country Farmhouse | 5 Peaceful Acres
Exterior

6. Romantic African-Inspired Studio on Alpaca Farm – Under the Stars

Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
The Plains
10.0 out of 10, Exceptional, (11 reviews)
"The entire stay was nothing but exceptional. The host was very informative, knowledgeable, and helped make the stay all it can be and then some."
United States
Joe D.
The price is AED 1,286
AED 1,762 total
includes taxes & fees
28 Sep - 29 Sep
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
Smart TV, books, computer monitors

7. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (38 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
United States
Avis V.
The price is AED 529
AED 1,115 total
includes taxes & fees
7 Oct - 8 Oct
Leesburg Hideaway- King Bed + Private Backyard
Interior

8. 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)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
The price is AED 826
AED 1,365 total
includes taxes & fees
28 Sep - 29 Sep
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Coffee/tea maker, fridge, microwave, oven

9. Renovated 3B/3B Home | Downtown | Private Fire Pit

Renovated 3B/3B Home | Downtown | Private Fire Pit
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (42 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is AED 1,232
AED 2,141 total
includes taxes & fees
28 Sep - 29 Sep
Renovated 3B/3B Home | Downtown | Private Fire Pit
Exterior

10. Storybook cottage on Leesburg's most historic block — walk to everything

Storybook cottage on Leesburg's most historic block — walk to everything
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (76 reviews)
"Spotless and super comfortable—exactly what we needed. We loved our quick weekend getaway here. The location is fantastic, just steps from downtown Leesburg’s charming shops, restaurants, and everything else. Highly recommend!"
United States
draje7
The price is AED 950
AED 1,621 total
includes taxes & fees
28 Sep - 29 Sep
Storybook cottage on Leesburg's most historic block — walk to everything
Bar (on property)

11. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.6 out of 10, Exceptional, (10 reviews)
"The property was great! Very clean and walkable to town. We had a wonderful time and Joe was great to work with! We would absolutely love to stay here again!"
United States
melissa b.
The price is AED 1,741
AED 2,732 total
includes taxes & fees
4 Oct - 5 Oct
Main Street USA -- Walk to Everything
Terrace/patio

12. Downtown Cottage with Fire Pit

Downtown Cottage with Fire Pit
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (23 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is AED 1,050
AED 1,919 total
includes taxes & fees
28 Sep - 29 Sep
Downtown Cottage with Fire Pit
Outdoor dining

13. "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 AED 797
AED 934 total
includes taxes & fees
28 Sep - 29 Sep
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Property grounds

14. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.2 out of 10, Wonderful, (11 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 AED 496
AED 963 total
includes taxes & fees
29 Sep - 30 Sep
Lunar Loft, with mountain views
Cottage (3 Bedrooms) | Interior

15. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is AED 1,495
AED 2,494 total
includes taxes & fees
22 Oct - 23 Oct
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Dining

16. ~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, (105 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is AED 566
AED 1,201 total
includes taxes & fees
28 Sep - 29 Sep
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Coffee/tea maker, fridge, microwave, oven

17. Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Well appointed and very walkable to nearby downtown."
United States
Sean S.
The price is AED 1,164
AED 2,057 total
includes taxes & fees
28 Sep - 29 Sep
Quaint Royal Cottage @ Historic Leesburg
Property grounds

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, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is AED 628
AED 774 total
includes taxes & fees
1 Oct - 2 Oct
Blue Mountain Cabin, secluded, perfect for couples, near main road
Coffee/tea maker, fridge, microwave, oven

19. Retreat in Historic Downtown Leesburg - Walkable to Everything!

Retreat in Historic Downtown Leesburg - Walkable to Everything!
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (28 reviews)
"Excellent location and nice little house."
United States
Ann B.
The price is AED 788
AED 1,646 total
includes taxes & fees
28 Sep - 29 Sep
Retreat in Historic Downtown Leesburg - Walkable to Everything!
Terrace/patio

20. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
The price is AED 1,366
AED 2,407 total
includes taxes & fees
30 Sep - 1 Oct
Mountaintop Cottage | Private Hot Tub
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

The Westin Washington Dulles Airport

The Westin Washington Dulles Airport

8/10 Good
"We stayed there for a night after oversea flight. Overall impression is good, especially the shuttle service. The room is big and the beddings are clean. I would have given it a five star if the carpet was cleaner and the room smelled better."
Letian 1-night trip
Posted 7 hours ago
The Westin Washington Dulles Airport

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.