Photo by Stephanie Sutton

Search Middleburg Cottage Rentals from CA $141

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is CA $410
CA $559 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $318
CA $530 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $141
CA $578 total
includes taxes & fees
Nov 19 - Nov 20
Woodsy Retreat with a Hot Tub and Seasonal Views!
A two-story house with a porch and a front door.

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, (44 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is CA $369
CA $782 total
includes taxes & fees
Nov 10 - Nov 11
Renovated 3B/3B Home | Downtown | Private Fire Pit
A covered deck with a table and chairs, overlooking a river and autumn foliage.

5. 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.
The price is CA $181
CA $714 total
includes taxes & fees
Nov 18 - Nov 19
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
United States
Tara G.
The price is CA $148
CA $639 total
includes taxes & fees
Nov 18 - Nov 19
Peaceful Lakefront Cottage with Mountain Views!
A stone house with a white picket fence, a front porch, and potted plants.

7. 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, (7 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 CA $480
CA $933 total
includes taxes & fees
Nov 22 - Nov 23
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A hot tub with a view of a forested landscape during sunset.

8. 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, (29 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 CA $141
CA $578 total
includes taxes & fees
Nov 11 - Nov 12
Cottage w/ Hot Tub and 100-Mile Valley Views!
A covered outdoor area with a fire pit, seating, and a view of the landscape.

9. 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 CA $346
CA $747 total
includes taxes & fees
Dec 8 - Dec 9
Mountain View Cottage with Hot Tub and River Views
A hot tub on an outdoor deck with a view of trees and hills.

10. 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 CA $519
CA $928 total
includes taxes & fees
Nov 10 - Nov 11
Mountain View Cottage | Hot Tub & Game Room
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, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
United States
Kevin D.
The price is CA $440
CA $819 total
includes taxes & fees
Nov 11 - Nov 12
Mountaintop Cottage | Private Hot Tub
A stone house with a white picket fence, a front porch, and potted plants.

12. 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 CA $575
CA $959 total
includes taxes & fees
Nov 22 - Nov 23
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.
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Learn more about Middleburg

Nestled in Virginia's horse country, this charming town invites you to explore historic inns and boutique wineries. Saddle up for a guided trail ride or join a polo match, then unwind at a cozy tavern with locally-sourced fare.

See all hotels in Middleburg
A vineyard with rows of grapevines under a clear sky.
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

Top reviews in Middleburg

A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.
Salamander Middleburg

Salamander Middleburg

Salamander Middleburg
Middleburg

10/10 Excellent

.
Canada
Ivanti
Reviewed December 7, 2025
Salamander Middleburg

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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.

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