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

Middleburg Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Middleburg vacation rentals

Desk, iron/ironing board, WiFi (free), bed sheets

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
9.8 out of 10, Exceptional, (27 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
$238 nightly
The price is $271
Aug 16 - Aug 17
Total with taxes and fees
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Exterior

2. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (62 reviews)
"Loved out stay! "
United States
Emilee
$367 nightly
The price is $394
Aug 2 - Aug 3
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Coffee/tea maker, fridge, microwave, oven

3. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (20 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.
$454 nightly
The price is $518
Aug 24 - Aug 25
Total with taxes and fees
Spacious Modern Home on Middleburg Horse Farm
Exterior

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

The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
Haymarket
8.6 out of 10, Excellent, (18 reviews)
"Excellent communication, great property!"
United States
Amy E.
$390 nightly
The price is $407
Aug 6 - Aug 7
Total with taxes and fees
The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
Property grounds

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.
$237 nightly
The price is $270
Aug 4 - Aug 5
Total with taxes and fees
Lunar Loft, with mountain views
Interior

6. Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
10.0 out of 10, Exceptional, (1 review)
"Amazingly comfortable place to call home for a few days with plenty of room for activities if you have to stay in! Bedrooms were lovely as were the bathrooms. Updated and very clean!!!! Host was extremely responsive and very easy to work with!! Bonus to bring our pup with us for the stay."
United States
K O.
$308 nightly
The price is $337
Aug 2 - Aug 3
Total with taxes and fees
Bluemont home just minutes to wineries, breweries, hiking and more!
Property grounds

7. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
9.8 out of 10, Exceptional, (12 reviews)
"Nice owner, great place"
United States
Leslie C.
$243 nightly
The price is $277
Aug 10 - Aug 11
Total with taxes and fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Terrace/patio

8. 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, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
$195 nightly
The price is $215
Aug 16 - Aug 17
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Dining

9. ~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, (96 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
$319 nightly
The price is $355
Aug 4 - Aug 5
Total with taxes and fees
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Exterior

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$380 nightly
The price is $419
Aug 5 - Aug 6
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Terrace/patio

11. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
$310 nightly
The price is $345
Aug 18 - Aug 19
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
Smart TV, books, computer monitors

12. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
$265 nightly
The price is $304
Aug 5 - Aug 6
Total with taxes and fees
Leesburg Hideaway- King Bed + Private Backyard
Smart TV, fireplace

13. Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (41 reviews)
"We had a great stay!"
United States
Olivia T.
$354 nightly
The price is $394
Aug 3 - Aug 4
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
Private kitchen

14. Bear Mountain Cottage

Bear Mountain Cottage
Paeonian Springs
10.0 out of 10, Exceptional, (20 reviews)
"Had a very relaxing few days away in a wonderful cabin."
United States
Cindy L.
Bear Mountain Cottage
Property grounds

15. 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, (39 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
$215 nightly
The price is $237
Aug 2 - Aug 3
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Interior

16. 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 3 - Aug 4
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

17. Charming 3BR Farmhouse • Wine Country Getaway

Charming 3BR Farmhouse • Wine Country Getaway
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.
$349 nightly
The price is $352
Aug 3 - Aug 4
Total with taxes and fees
Charming 3BR Farmhouse • Wine Country Getaway
Smart TV

18. 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, (18 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.
$391 nightly
The price is $435
Aug 20 - Aug 21
Total with taxes and fees
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Outdoor dining

19. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
$219 nightly
The price is $244
Aug 10 - Aug 11
Total with taxes and fees
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Outdoor dining

20. "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
Aug 2 - Aug 3
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middleburg Hotel Reviews

Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

10/10 Excellent
"Very helpful staff. Nice breakfast."
Bruce 1-night trip
Posted less than an hour 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 $233 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?

Harpers Ferry: Fireplace • Patio • Near River Tubing & Downtown Harpers Ferry: This vacation home rental outside of Middleburg offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 National Sporting Library & Museum, whereas Glenwood Park is one spot to enjoy nature. 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.