A sunrise over a mountainous landscape with layers of clouds.

Search Vacation Homes 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 HK$1,177
HK$2,290 total
includes taxes & fees
19 Oct - 20 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 HK$2,386
HK$4,616 total
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 HK$1,483
HK$3,157 total
includes taxes & fees
14 Oct - 15 Oct
1910 Farmhouse on 6 Acres • VA Wine Country
A deck with outdoor seating and a lake view.

4. 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 HK$314
HK$1,938 total
includes taxes & fees
22 Oct - 23 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

5. 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 HK$3,720
HK$6,223 total
includes taxes & fees
21 Oct - 22 Oct
Main Street USA -- Walk to Everything
Fire pit crackling with seasoned firewood

6. 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 HK$2,029
HK$4,556 total
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage, Walk to Downtown, Porch Swings
A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

7. 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 HK$1,899
HK$4,308 total
includes taxes & fees
9 Nov - 10 Nov
Downtown Cottage with Fire Pit
A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a window providing natural light.

8. 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 HK$2,132
HK$4,549 total
includes taxes & fees
19 Oct - 20 Oct
Historic Downtown Home with Fire Pit
Game Room (1)

9. 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 HK$5,768
HK$10,453 total
includes taxes & fees
21 Oct - 22 Oct
Still Meadow Farm
A large estate with multiple buildings, expansive outdoor seating areas, and surrounding vineyards.

10. 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, (77 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 HK$2,337
HK$4,051 total
includes taxes & fees
3 Nov - 4 Nov
Storybook cottage on Leesburg's most historic block — walk to everything
A bedroom with a large bed, two bedside lamps, a potted plant, and a small ottoman.

11. 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 HK$628
HK$1,342 total
includes taxes & fees
19 Oct - 20 Oct
Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outside through a window.

12. 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 HK$2,029
HK$4,192 total
includes taxes & fees
14 Oct - 15 Oct
Retreat in Historic Downtown Leesburg - Walkable to Everything!
A narrow hallway with a wooden floor, metal shelving units, and a window with blinds.

13. 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 HK$1,442
HK$3,791 total
includes taxes & fees
27 Oct - 28 Oct
Downtown Retreat with 2 Primary Suites
A kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

14. 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 HK$1,925
HK$4,419 total
includes taxes & fees
2 Nov - 3 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

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

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Front Royal
The price is HK$1,099
HK$3,107 total
includes taxes & fees
2 Nov - 3 Nov
Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
A sectional sofa with a storage ottoman, a large potted plant, and a lamp.

16. Stylish Studio with Kitchenette

Stylish Studio with Kitchenette
Sterling
10.0 out of 10, Exceptional, (1 review)
"Very organized and had tons of quality of life features."
United States
Hunter J.
The price is HK$746
HK$1,431 total
includes taxes & fees
3 Nov - 4 Nov
Stylish Studio with Kitchenette
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

17. 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 HK$1,262
HK$2,387 total
includes taxes & fees
27 Oct - 28 Oct
Mountain home w/ hot tub & sunroom
A spacious living room with a green sofa set, a coffee table, and a fireplace. There is a kitchen in the background with a large window overlooking a deck.

18. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! So peaceful and beautiful property. Andrea is a great host!"
United States
Erin C.
The price is HK$1,311
HK$3,223 total
includes taxes & fees
3 Nov - 4 Nov
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding door.

19. Cozy 3BR Retreat | Perfect for Families & Groups

Cozy 3BR Retreat | Perfect for Families & Groups
Apple Mountain Lake
The price is HK$948
HK$2,045 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 3BR Retreat | Perfect for Families & Groups
A two-story house with a covered porch and a staircase leading to the upper level.

20. A private 2BR & living area w/ patio for 4

A private 2BR & living area w/ patio for 4
Manassas Park
9.0 out of 10, Wonderful, (12 reviews)
"Place was clean and comfortable. It was a very nice neighborhood!"
United States
Terri G.
The price is HK$1,059
HK$2,235 total
includes taxes & fees
18 Oct - 19 Oct
A private 2BR & living area w/ patio for 4
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

Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

10/10 Excellent
"Gonna stay again"
Corrie 1-night trip
Posted 6 hours ago
Hyatt Place Herndon Dulles Airport East

Find out more about Middleburg

Middleburg Vacation Homes information

Number of reviews
316
Accommodation
279 Vacation Homes
Lowest Price
HK$1,342
Highest Price
HK$10,453

Explore a world of travel with Expedia