Autumn morning mist shrouds the Shenandoah Mountains in the Blue Ridge Mountains of Virginia.

Middleburg Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middleburg vacation rentals

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

1. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (64 reviews)
"Loved out stay! "
United States
Emilee
$372 nightly
The price is $399
Aug 30 - Aug 31
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
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.

2. 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
9.8 out of 10, Exceptional, (28 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
$240 nightly
The price is $274
Aug 23 - Aug 24
Total with taxes and fees
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

3. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful house in a beautiful location. The house was very good for relaxing and hanging out with old friends with its open concept. Bedrooms were on the small side but functional as were the bathrooms. The kitchen was very nice and a nice coffee bar was provided with a Nespresso machine and milk frother."
United States
Mark W.
$458 nightly
The price is $522
Aug 24 - Aug 25
Total with taxes and fees
Spacious Modern Home on Middleburg Horse Farm
A cabin with a triangular roof, large windows, and a deck area.

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.
$371 nightly
The price is $388
Aug 24 - Aug 25
Total with taxes and fees
The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
A fenced grassy field with a clear sky and distant hills.

5. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
$240 nightly
The price is $274
Aug 24 - Aug 25
Total with taxes and fees
Lunar Loft, with mountain views

6. Historic Farmhouse, Fully Renovated in Fall 2023

Historic Farmhouse, Fully Renovated in Fall 2023
Loudoun County
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
$503 nightly
The price is $552
Sep 14 - Sep 15
Total with taxes and fees
Historic Farmhouse, Fully Renovated in Fall 2023
A stone building with a central entrance, a stone staircase, and a landscaped garden.

7. 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.
$480 nightly
The price is $515
Aug 23 - Aug 24
Total with taxes and fees
Romantic African-Inspired Studio on Alpaca Farm – Under the Stars
A spacious kitchen with a central island, a dining area with a staircase, and a view of the living room.

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, (24 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
$349 nightly
The price is $398
Aug 23 - Aug 24
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A modern living room with a sofa, yellow chairs, a dining table, and a TV mounted on the wall.

9. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (37 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
United States
Avis V.
$268 nightly
The price is $308
Aug 24 - Aug 25
Total with taxes and fees
Leesburg Hideaway- King Bed + Private Backyard
A two-story house with a covered patio and a stone fireplace.

10. Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool
bluemont
9.8 out of 10, Exceptional, (272 reviews)
"The house and pool are well maintained and the location was perfect for both hiking and visiting wineries."
United States
Anonymous traveler
$1,686 nightly
The price is $1,922
Sep 4 - Sep 5
Total with taxes and fees
Breathtaking View with an Indoor Pool
A spacious room with a large dining table, white chairs, and a ceiling fan.

11. 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, (102 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
$317 nightly
The price is $353
Aug 24 - Aug 25
Total with taxes and fees
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

12. 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, (42 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
$216 nightly
The price is $238
Aug 23 - Aug 24
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.

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.
$247 nightly
The price is $265
Aug 23 - Aug 24
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

14. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Aug 24 - Aug 25
Total with taxes and fees
The Pond Cabin
A hammock, wicker chairs, and a view of trees through a geodesic dome structure.

15. Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
Leesburg
9.0 out of 10, Wonderful, (13 reviews)
"What an excellent stay! Ayda was an amazing host. The dome is very private and wonderfully outfitted. The hot tub was awesome and everything was clean and so comfy. In summer I can only imagine it is even more secluded as the trees leaf out!! Highly recommended and planning another stay. "
United States
Carter S.
$270 nightly
The price is $299
Aug 26 - Aug 27
Total with taxes and fees
Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

16. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.6 out of 10, Exceptional, (8 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.
$659 nightly
The price is $738
Sep 3 - Sep 4
Total with taxes and fees
Main Street USA -- Walk to Everything
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

17. 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.
$401 nightly
The price is $442
Aug 23 - Aug 24
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A large estate with multiple buildings, expansive outdoor seating areas, and surrounding vineyards.

18. 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, (73 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
$335 nightly
The price is $386
Aug 24 - Aug 25
Total with taxes and fees
Storybook cottage on Leesburg's most historic block — walk to everything
A sunroom with a large glass wall, a dining table set for four, and a ceiling fan.

19. Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (25 reviews)
"Excellent property!"
United States
Michelle R.
$389 nightly
The price is $433
Aug 25 - Aug 26
Total with taxes and fees
Log Cabin w/ Hot Tub & Waterfront Patio!
A patio area with a table and chairs, a small brick building in the background, and a wooden fence.

20. Historic 2-Bedroom in Old Town Warrenton, Virginia

Historic 2-Bedroom in Old Town Warrenton, Virginia
Warrenton
10.0 out of 10, Exceptional, (76 reviews)
"Great stay and utterly charming!"
United States
Jimmy
$232 nightly
The price is $254
Aug 24 - Aug 25
Total with taxes and fees
Historic 2-Bedroom in Old Town Warrenton, Virginia
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

8/10 Good
"The hotel is close to the metro walking distance No restaurant in the hotel have to go out yo eat ."
Glenn 1-night trip
Posted 4 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 $180 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?

A unique mountaintop getaway overlooking Willow Croft Winery. : This vacation home rental outside of Middleburg is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Middleburg?

Expedia has 12 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.