A sunrise over a mountainous landscape with layers of clouds.

Search Middleburg Cottages

  • 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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$348 nightly
The price is $373
Sep 30 - Oct 1
Total with taxes and fees
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, (26 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
$326 nightly
The price is $372
Sep 28 - Sep 29
Total with taxes and fees
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, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
$380 nightly
The price is $424
Oct 4 - Oct 5
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

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

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 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.
$429 nightly
The price is $479
Sep 30 - Oct 1
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveler
$363 nightly
The price is $406
Oct 12 - Oct 13
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
A two-story house with a porch and a front door.

6. 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.
$513 nightly
The price is $576
Sep 28 - Sep 29
Total with taxes and fees
Renovated 3B/3B Home | Downtown | Private Fire Pit
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, (41 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.
$464 nightly
The price is $518
Oct 14 - Oct 15
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
A stone house with a white picket fence, a front porch, and potted plants.

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

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
$591 nightly
The price is $679
Oct 22 - Oct 23
Total with taxes and fees
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A hot tub on an outdoor deck with a view of trees and hills.

9. 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.
$611 nightly
The price is $674
Sep 29 - Sep 30
Total with taxes and fees
Mountain View Cottage | Hot Tub & Game Room
A covered outdoor area with a fire pit, seating, and a view of the landscape.

10. 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.
$610 nightly
The price is $673
Sep 30 - Oct 1
Total with taxes and fees
Mountain View Cottage with Hot Tub and River Views
A covered outdoor area with a fire pit, seating, and a view of the landscape.

11. 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.
$594 nightly
The price is $655
Sep 30 - Oct 1
Total with taxes and fees
Mountaintop Cottage | Private Hot Tub
A hot tub under a wooden pergola with a grassy yard and trees in the background.

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

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.6 out of 10, Exceptional, (39 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
$656 nightly
The price is $724
Oct 22 - Oct 23
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
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.
$565 nightly
The price is $650
Oct 22 - Oct 23
Total with taxes and fees
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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

Wingate by Wyndham Chantilly / Dulles Airport

Wingate by Wyndham Chantilly / Dulles Airport

8/10 Good
"La limpieza, buena atencion, y un excelente parqueo"
Martha 1-night trip
Posted 5 hours ago
Wingate by Wyndham Chantilly / Dulles Airport

Find out more about Middleburg

Middleburg Cottages information

Number of reviews
211
Accommodation
96 Cottages
Lowest Price
$372
Highest Price
$724

Frequently asked questions

Why book your cottage in Middleburg with Expedia?
We think that a vacay should be simple, so if you're seeking cottages in Middleburg at a competitive rate, Expedia has you covered. Save cash and go for an inexpensive option surrounded by nature, or book an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Middleburg?
The quickest way to find cheap cottages in Middleburg is with Expedia's handy filter tool. Narrow your search by amenities, budget and star rating to access awesome bargains in a few clicks.
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.

Explore a world of travel with Expedia