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
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
$239 nightly
The price is $272
Oct 12 - Oct 13
Total with taxes and fees
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
$256 nightly
The price is $292
Oct 11 - Oct 12
Total with taxes and fees
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.
$369 nightly
The price is $396
Oct 12 - Oct 13
Total with taxes and fees
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.
$528 nightly
The price is $602
Oct 19 - Oct 20
Total with taxes and fees
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.
$360 nightly
The price is $374
Nov 3 - Nov 4
Total with taxes and fees
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, (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.
$237 nightly
The price is $270
Oct 12 - Oct 13
Total with taxes and fees
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
$223 nightly
The price is $246
Oct 18 - Oct 19
Total with taxes and fees
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.
$399 nightly
The price is $402
Oct 12 - Oct 13
Total with taxes and fees
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.
$344 nightly
The price is $392
Oct 12 - Oct 13
Total with taxes and fees
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.
$346 nightly
The price is $386
Oct 28 - Oct 29
Total with taxes and fees
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.
$342 nightly
The price is $381
Oct 22 - Oct 23
Total with taxes and fees
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.
$351 nightly
The price is $391
Oct 21 - Oct 22
Total with taxes and fees
~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)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$347 nightly
The price is $383
Nov 2 - Nov 3
Total with taxes and fees
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.
$150 nightly
The price is $171
Oct 18 - Oct 19
Total with taxes and fees
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.
$354 nightly
The price is $394
Oct 26 - Oct 27
Total with taxes and fees
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.
$117 nightly
The price is $138
Oct 15 - Oct 16
Total with taxes and fees
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.
$403 nightly
The price is $445
Oct 27 - Oct 28
Total with taxes and fees
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)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
$233 nightly
The price is $257
Oct 14 - Oct 15
Total with taxes and fees
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.
$245 nightly
The price is $263
Oct 11 - Oct 12
Total with taxes and fees
"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.
$368 nightly
The price is $410
Oct 26 - Oct 27
Total with taxes and fees
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

Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

10/10 Excellent
"Well maintained facilities."
John 4-night trip
Posted 2 hours ago
Hyatt Place Herndon Dulles Airport East

Find out more about Middleburg

Everything you need to know about Middleburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleburg. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middleburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleburg rentals

At Expedia, we put the best Middleburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middleburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.