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Holiday Homes in Middleburg

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 €281
includes taxes & fees
29 Oct - 30 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 €518
includes taxes & fees
26 Oct - 27 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 €338
includes taxes & fees
17 Nov - 18 Nov
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, (13 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
United States
Dawn S.
The price is €235
includes taxes & fees
26 Oct - 27 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A modern living room with a sofa, yellow chairs, a dining table, and a TV mounted on the wall.

5. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (39 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
United States
Avis V.
Leesburg Hideaway- King Bed + Private Backyard
A dining area with a wooden ceiling, a kitchen with blue cabinets, and a tiled floor.

6. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.6 out of 10, Exceptional, (13 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.
Main Street USA -- Walk to Everything
A yellow house with a porch, a front door, and two windows.

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, (78 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 €484
includes taxes & fees
22 Nov - 23 Nov
Storybook cottage on Leesburg's most historic block — walk to everything
A narrow hallway with a wooden floor, metal shelving units, and a window with blinds.

8. 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 €470
includes taxes & fees
26 Oct - 27 Oct
Downtown Retreat with 2 Primary Suites
A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a window providing natural light.

9. 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 €489
includes taxes & fees
26 Oct - 27 Oct
Historic Downtown Home with Fire Pit
A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

10. 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.
Downtown Cottage with Fire Pit
Fire pit crackling with seasoned firewood

11. 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 €525
includes taxes & fees
22 Nov - 23 Nov
Charming Cottage, Walk to Downtown, Porch Swings
A hot tub under a wooden pergola with a view of autumn trees.

12. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay "
United States
Lauren O.
The price is €354
includes taxes & fees
26 Oct - 27 Oct
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Game Room (1)

13. 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 €1,172
includes taxes & fees
28 Oct - 29 Oct
Still Meadow Farm
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 €466
includes taxes & fees
27 Oct - 28 Oct
Renovated 3B/3B Home | Downtown | Private Fire Pit
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, (121 reviews)
"We had a quick stay but it was perfect for what we needed. "
United States
Deana B.
The price is €156
includes taxes & fees
29 Oct - 30 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.

16. 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, (30 reviews)
"Excellent location and nice little house."
United States
Ann B.
The price is €433
includes taxes & fees
27 Oct - 28 Oct
Retreat in Historic Downtown Leesburg - Walkable to Everything!
A sectional sofa with a storage ottoman, a large potted plant, and a lamp.

17. 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 €173
includes taxes & fees
25 Oct - 26 Oct
Stylish Studio with Kitchenette
A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

18. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6

Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
Front Royal
The price is €363
includes taxes & fees
26 Oct - 27 Oct
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
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.

19. 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 €365
includes taxes & fees
2 Nov - 3 Nov
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

20. 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 €278
includes taxes & fees
3 Nov - 4 Nov
Mountain home w/ hot tub & sunroom
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

DoubleTree by Hilton Washington Dulles Airport

DoubleTree by Hilton Washington Dulles Airport

10/10 Excellent
"Excellent customer service and clean"
Yonie 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Washington Dulles Airport

Find out more about Middleburg

Middleburg Holiday Homes information

Number of reviews
441
Accommodation
290 Holiday Homes
Lowest Price
€156
Highest Price
€1,172