A sunrise over a mountainous landscape with layers of clouds.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Middleburg holiday homes

A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

1. super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.6 out of 10, Exceptional, (19 reviews)
"The area was surrounded by horses, Horse farms all around, which was lovely. Very quite and peaceful. Enjoyed my time there."
United States
Lynette
The price is £221
includes taxes & fees
13 Oct - 14 Oct
super cosy cottage with high speed internet!
A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

2. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (22 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 £456
includes taxes & fees
19 Oct - 20 Oct
Spacious Modern Home on Middleburg Horse Farm
A two-story house with a porch, surrounded by trees and grass.

3. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
The price is £314
includes taxes & fees
12 Oct - 13 Oct
1910 Farmhouse on 6 Acres • VA Wine Country
A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

4. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.6 out of 10, Exceptional, (12 reviews)
"The property was great! Very clean and walkable to town. We had a wonderful time and Joe was great to work with! We would absolutely love to stay here again!"
United States
melissa b.
The price is £607
includes taxes & fees
18 Oct - 19 Oct
Main Street USA -- Walk to Everything
A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

5. Downtown Cottage with Fire Pit

Downtown Cottage with Fire Pit
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (23 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is £380
includes taxes & fees
27 Oct - 28 Oct
Downtown Cottage with Fire Pit
A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a window providing natural light.

6. Historic Downtown Home with Fire Pit

Historic Downtown Home with Fire Pit
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Well appointed and very walkable to nearby downtown."
United States
Sean S.
The price is £404
includes taxes & fees
27 Oct - 28 Oct
Historic Downtown Home with Fire Pit
A large estate with multiple buildings, expansive outdoor seating areas, and surrounding vineyards.

7. Storybook cottage on Leesburg's most historic block — walk to everything

Storybook cottage on Leesburg's most historic block — walk to everything
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (76 reviews)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is £391
includes taxes & fees
9 Nov - 10 Nov
Storybook cottage on Leesburg's most historic block — walk to everything
Fire pit crackling with seasoned firewood

8. Charming Cottage, Walk to Downtown, Porch Swings

Charming Cottage, Walk to Downtown, Porch Swings
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (1 review)
"it was a clean house and quite area. perfect!"
United States
John S.
The price is £435
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage, Walk to Downtown, Porch Swings
A kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

9. 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 £425
includes taxes & fees
2 Nov - 3 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outside through a window.

10. Retreat in Historic Downtown Leesburg - Walkable to Everything!

Retreat in Historic Downtown Leesburg - Walkable to Everything!
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (29 reviews)
"Excellent location and nice little house."
United States
Ann B.
The price is £423
includes taxes & fees
11 Oct - 12 Oct
Retreat in Historic Downtown Leesburg - Walkable to Everything!
A narrow hallway with a wooden floor, metal shelving units, and a window with blinds.

11. Downtown Retreat with 2 Primary Suites

Downtown Retreat with 2 Primary Suites
Leesburg
10.0 out of 10, Exceptional, (1 review)
"Very clean, larger unit than expected. Very comfortable and close to many shops and restaurants. Would highly recommend! We had a wonderful stay."
United States
Tyler W.
The price is £355
includes taxes & fees
27 Oct - 28 Oct
Downtown Retreat with 2 Primary Suites
Game Room (1)

12. Still Meadow Farm

Still Meadow Farm
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"Still Meadow is a beautiful place to stay, super clean, We would definitely recommend. Host was responsive and accommodating."
United States
Jodie J.
The price is £991
includes taxes & fees
21 Oct - 22 Oct
Still Meadow Farm
A deck with outdoor seating and a lake view.

13. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is £161
includes taxes & fees
12 Oct - 13 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

14. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"
United States
Mollie S.
The price is £232
includes taxes & fees
28 Oct - 29 Oct
Mountain home w/ hot tub & sunroom
A bedroom with a large bed, two bedside lamps, a potted plant, and a small ottoman.

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

Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
Sterling
9.8 out of 10, Exceptional, (120 reviews)
"We had a quick stay but it was perfect for what we needed. "
United States
Deana B.
The price is £132
includes taxes & fees
20 Oct - 21 Oct
Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
A cozy dining area with a table and chairs, a view of a balcony with a railing, and a warm interior with wooden walls.

16. Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Shannondale
10.0 out of 10, Exceptional, (4 reviews)
"My family and ai had an amazing stay at Deb and Alex’s rental in WV! It was easy to check-in, very clean, and had convenient amenities! Would definitely consider staying with them again!"
United States
Anonymous traveller
The price is £493
includes taxes & fees
5 Nov - 6 Nov
Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

17. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Front Royal
Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
A modern house with a covered patio, outdoor seating, and a view of the surrounding landscape.

18. A Luxurious Home for Rest and Work.

A Luxurious Home for Rest and Work.
Ashburn
10.0 out of 10, Exceptional, (28 reviews)
"We had a lovely stay at this home! "
United States
Kristina P.
The price is £556
includes taxes & fees
14 Oct - 15 Oct
A Luxurious Home for Rest and Work.
Room

19. Eagles Nest. Luxury and leisure, with a million dollar view.

Eagles Nest. Luxury and leisure, with a million dollar view.
Harpers Ferry
The price is £629
includes taxes & fees
12 Oct - 13 Oct
Eagles Nest. Luxury and leisure, with a million dollar view.
A spacious dining area with a wooden table and chairs, large windows with a view of trees, and a stone wall in the background.

20. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is £297
includes taxes & fees
3 Nov - 4 Nov
Stone Cabin on Valley View: Fire Pit + 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

Wingate by Wyndham Chantilly / Dulles Airport

Wingate by Wyndham Chantilly / Dulles Airport

8/10 Good
"Staff was great. Plenty of parking. Room was clean, needs a little upgrade."
Ulysses 7-night trip
Posted less than an hour ago
Wingate by Wyndham Chantilly / Dulles Airport

Find out more about Middleburg

Middleburg Holiday Homes information

Number of reviews
416
Accommodation
284 Holiday Homes
Lowest Price
£132
Highest Price
£991