A sunrise over a mountainous landscape with layers of clouds.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middleburg cottages

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, (67 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is €357
includes taxes & fees
22 Nov - 23 Nov
18th Century Stone Cottage minutes from historic Middleburg
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

2. 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, (27 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is €385
includes taxes & fees
22 Nov - 23 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A modern building with large windows, a deck, and a stone wall.

3. 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, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
The price is €409
includes taxes & fees
12 Nov - 13 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!
A two-story house with a porch, a garage, and a fenced yard.

4. 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 €466
includes taxes & fees
27 Oct - 28 Oct
Renovated 3B/3B Home | Downtown | Private Fire Pit
A hot tub with a view of a forested landscape during sunset.

5. 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, (28 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
United States
Keri L.
The price is €354
includes taxes & fees
29 Oct - 30 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A stone house with a white picket fence, a front porch, and potted plants.

6. 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 €605
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A hot tub on a deck with a view of a lake and forest.

7. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

8. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (29 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A hot tub under a wooden pergola with a grassy yard and trees in the background.

9. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Property grounds

10. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Front Royal
The price is €433
includes taxes & fees
3 Nov - 4 Nov
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
A covered outdoor area with a fire pit, seating, and a view of the landscape.

11. Mountain View Cottage with Hot Tub and River Views

Mountain View Cottage with Hot Tub and River Views
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
United States
MaryBeth C.
The price is €610
includes taxes & fees
9 Nov - 10 Nov
Mountain View Cottage with Hot Tub and River Views
A hot tub on an outdoor deck with a view of trees and hills.

12. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is €610
includes taxes & fees
3 Nov - 4 Nov
Mountain View Cottage | Hot Tub & Game Room
A stone house with a white picket fence, a front porch, and potted plants.

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

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
United States
Corky F.
The price is €620
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A covered outdoor area with a fire pit, seating, and a view of the landscape.

14. 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 €564
includes taxes & fees
8 Nov - 9 Nov
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

DoubleTree by Hilton Washington Dulles Airport

DoubleTree by Hilton Washington Dulles Airport

10/10 Excellent
"Excellent customer service and clean"
Yonie 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Washington Dulles Airport

Find out more about Middleburg

Middleburg Cottages information

Number of reviews
313
Accommodation
96 Cottages
Lowest Price
€354
Highest Price
€620

Frequently asked questions

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What is there to do in Middleburg near my cottage?
You'll find loads of fun things to fill your itinerary with in Middleburg. Explore popular attractions like Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. Glenwood Park, Red Fox Fine Art and The Sporting Gallery also appeal to many visitors.