A sunrise over a mountainous landscape with layers of clouds.

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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 vacation 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 AEDĀ 606
AEDĀ 1,143 total
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 AEDĀ 1,238
AEDĀ 2,299 total
includes taxes & fees
5 Nov - 6 Nov
Spacious Modern Home on Middleburg Horse Farm
covered patio

3. Hunters Retreat with High Speed Internet

Hunters Retreat with High Speed Internet
Middleburg
10.0 out of 10, Exceptional, (6 reviews)
"We had the best fall weekend and the property is amazing "
United States
Kelly T.
Hunters Retreat with High Speed Internet
A two-story house with a porch, surrounded by trees and grass.

4. 1910 Farmhouse on 6 Acres ā€¢ VA Wine Country

1910 Farmhouse on 6 Acres ā€¢ 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 AEDĀ 635
AEDĀ 1,423 total
includes taxes & fees
17 Nov - 18 Nov
1910 Farmhouse on 6 Acres ā€¢ VA Wine Country
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 hot tub in a forested area with a rocky ground and trees.

6. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is AEDĀ 367
AEDĀ 1,353 total
includes taxes & fees
5 Nov - 6 Nov
The Blue Jay | New House in the Woods w/ Hot Tub
A deck with outdoor seating and a lake view.

7. 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, (14 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 AEDĀ 129
AEDĀ 956 total
includes taxes & fees
26 Oct - 27 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A yellow house with a porch, a front door, and two windows.

8. Storybook cottage on Leesburg's most historic block ā€” walk to everything

Storybook cottage on Leesburg's most historic block ā€” 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 AEDĀ 950
AEDĀ 1,722 total
includes taxes & fees
26 Oct - 27 Oct
Storybook cottage on Leesburg's most historic block ā€” walk to everything
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 AEDĀ 1,176
AEDĀ 2,426 total
includes taxes & fees
2 Nov - 3 Nov
Historic Downtown Home with Fire Pit
Fire pit crackling with seasoned firewood

10. 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.
Charming Cottage, Walk to Downtown, Porch Swings
A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outside through a window.

11. 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.
Retreat in Historic Downtown Leesburg - Walkable to Everything!
A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

12. 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 AEDĀ 889
AEDĀ 2,054 total
includes taxes & fees
27 Oct - 28 Oct
Downtown Cottage with Fire Pit
A kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

13. 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 AEDĀ 897
AEDĀ 2,064 total
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.

14. 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 AEDĀ 294
AEDĀ 628 total
includes taxes & fees
3 Nov - 4 Nov
Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.
Game Room (1)

15. 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 AEDĀ 2,700
AEDĀ 4,893 total
includes taxes & fees
29 Oct - 30 Oct
Still Meadow Farm
A narrow hallway with a wooden floor, metal shelving units, and a window with blinds.

16. 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.
Downtown Retreat with 2 Primary Suites
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 | 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 AEDĀ 544
AEDĀ 1,487 total
includes taxes & fees
3 Nov - 4 Nov
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
A sectional sofa with a storage ottoman, a large potted plant, and a lamp.

18. 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.
Stylish Studio with Kitchenette
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

19. 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 AEDĀ 605
AEDĀ 1,136 total
includes taxes & fees
5 Nov - 6 Nov
Mountain home w/ hot tub & sunroom
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, (15 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is AEDĀ 614
AEDĀ 1,416 total
includes taxes & fees
27 Oct - 28 Oct
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

Best Western Dulles Airport Inn

Best Western Dulles Airport Inn

8/10 Good
"Clean room, ok breakfast. Good shuttle. Did the job for a quick one night stay for early flight out"
Paul 1-night trip
Posted 1 hour ago
Best Western Dulles Airport Inn