A sunrise over a mountainous landscape with layers of clouds.

Search Cottages in Middleburg

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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.
The price is SAR 1,032
SAR 1,487 total
includes taxes & fees
18 Oct - 19 Oct
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)
"Fun place to stay!!!"
United States
Theresa R.
The price is SAR 845
SAR 1,485 total
includes taxes & fees
4 Oct - 5 Oct
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

3. 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.
The price is SAR 541
SAR 1,869 total
includes taxes & fees
7 Oct - 8 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A modern building with large windows, a deck, and a stone wall.

4. 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)
"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 SAR 642
SAR 1,565 total
includes taxes & fees
4 Oct - 5 Oct
Woodsy Retreat with a Hot Tub and Seasonal Views!
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
The price is SAR 593
SAR 1,726 total
includes taxes & fees
12 Oct - 13 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A hot tub on a deck with a view of a lake and forest.

6. 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 two-story house with a porch and a front door.

7. 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 SAR 1,520
SAR 2,669 total
includes taxes & fees
1 Oct - 2 Oct
Renovated 3B/3B Home | Downtown | Private Fire Pit
A hot tub on an outdoor deck with a view of trees and hills.

8. 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 SAR 1,374
SAR 2,824 total
includes taxes & fees
7 Oct - 8 Oct
Mountain View Cottage | Hot Tub & Game Room
A stone house with a white picket fence, a front porch, and potted plants.

9. 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 SAR 1,528
SAR 2,550 total
includes taxes & fees
22 Oct - 23 Oct
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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.
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.
The price is SAR 1,397
SAR 2,447 total
includes taxes & fees
6 Oct - 7 Oct
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.
The price is SAR 1,489
SAR 2,922 total
includes taxes & fees
22 Oct - 23 Oct
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
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

Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"Great place, and nice staff"
Mohamed 1-night trip
Posted 9 hours ago
Salamander Resort And Spa

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.