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

Middleburg Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middleburg holiday rentals

Desk, iron/ironing board, free WiFi, 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, (28 reviews)
"Easy to get in and out, and the property was clean and tidy!"
United States
Cameron H.
The price is HK$1,177
HK$2,147 total
includes taxes & fees
16 Aug - 17 Aug
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, (64 reviews)
"Loved out stay! "
United States
Emilee
The price is HK$2,157
HK$3,132 total
includes taxes & fees
17 Aug - 18 Aug
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.
The price is HK$1,773
HK$4,097 total
includes taxes & fees
1 Sept - 2 Sept
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, (19 reviews)
"Excellent communication, great property!"
United States
Amy E.
The price is HK$1,454
HK$3,140 total
includes taxes & fees
13 Aug - 14 Aug
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.
The price is HK$727
HK$1,715 total
includes taxes & fees
17 Aug - 18 Aug
Lunar Loft, with mountain views
Property grounds

6. 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.
The price is HK$953
HK$2,115 total
includes taxes & fees
25 Aug - 26 Aug
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
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, (36 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
Leesburg Hideaway- King Bed + Private Backyard
Interior

8. 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.
The price is HK$1,059
HK$2,730 total
includes taxes & fees
13 Aug - 14 Aug
Bluemont home just minutes to wineries, breweries, hiking and more!
Exterior

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
The price is HK$1,138
HK$3,410 total
includes taxes & fees
25 Aug - 26 Aug
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Coffee/tea maker, fridge, microwave, oven

10. 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.
The price is HK$2,503
HK$4,629 total
includes taxes & fees
9 Sept - 10 Sept
Historic Farmhouse, Fully Renovated in Fall 2023
Outdoor spa tub

11. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay and the property was exactly what we were looking for in a mountain getaway peaceful, private, and immersed in the woods with beautiful views and a relaxing atmosphere.The home was clean, quiet, and met our needs well for a restful escape. The hosts were communicative and supportive, although we did not need to reach out during our stay.The driveway is definitely mountain-style, so guests should come prepared and be mindful of the vehicle they bring, but the secluded setting...
United States
B S.
The price is HK$785
HK$3,003 total
includes taxes & fees
31 Aug - 1 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
Smart TV, fireplace, ping pong

12. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (75 reviews)
"This was an absolutely amazing stay. Beautiful location, extremely comfortable. Well stocked kitchen. Wonderful hot tub. Perfection for a getaway."
United States
Andrew L.
The price is HK$785
HK$2,907 total
includes taxes & fees
18 Aug - 19 Aug
Blue Ridge Getaway - Sunset Views, A.T. Access
1 bedroom, desk, iron/ironing board, free WiFi

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

Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
Sterling
9.8 out of 10, Exceptional, (119 reviews)
"We had a quick stay but it was perfect for what we needed. "
United States
Deana B.
The price is HK$628
HK$1,163 total
includes taxes & fees
30 Aug - 31 Aug
Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
Interior

14. 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.
The price is HK$1,765
HK$3,121 total
includes taxes & fees
17 Aug - 18 Aug
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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, (40 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is HK$1,491
HK$1,878 total
includes taxes & fees
20 Aug - 21 Aug
Blue Mountain Cabin, secluded, perfect for couples, near main road
Terrace/patio

16. Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (40 reviews)
"Nice view . Perfect for a boys stay"
United States
Ahffan k.
The price is HK$1,028
HK$3,350 total
includes taxes & fees
26 Aug - 27 Aug
Rebels Rest - Cabin with Enchanting Sunset Views!
Dining

17. 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, (99 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is HK$1,412
HK$2,944 total
includes taxes & fees
24 Aug - 25 Aug
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Smart TV, fireplace

18. 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, (42 reviews)
"We had a great stay!"
United States
Olivia T.
The price is HK$785
HK$3,107 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cabin a Stone's Throw From the A.T.!
Terrace/patio

19. 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.
The price is HK$785
HK$2,706 total
includes taxes & fees
18 Aug - 19 Aug
Woodsy Retreat with a Hot Tub and Seasonal Views!
Smart TV

20. 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, (19 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 HK$785
HK$3,090 total
includes taxes & fees
25 Aug - 26 Aug
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
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

10/10 Excellent
"Very clean, simple and quiet, Close to activities we wanted to do."
Denisa 1-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
  • Use the map to find apartments and other holiday homes in the Middleburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middleburg while they last

Look no further and take a look at our great range of rental properties in Middleburg!

Frequently asked questions

Can I find holiday rentals in Middleburg?

Yes, there are holiday rentals in Middleburg close to National Sporting Library & Museum, or you can select a more secluded option if you're looking for 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 holiday rentals that Middleburg has to offer?

Terra Alta - Incredible River Views and Hot Tub!: This holiday home rental outside of Middleburg is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Middleburg?

Expedia has 12 holiday 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 holiday rental in Middleburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleburg. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.