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Our top choices for Leesburg holiday homes

1. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (40 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
United States
Avis V.
The price is £231
includes taxes & fees
19 Nov - 20 Nov
Leesburg Hideaway- King Bed + Private Backyard

2. 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 £360
includes taxes & fees
18 Nov - 19 Nov
Downtown Retreat with 2 Primary Suites

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

Retreat in Historic Downtown Leesburg - Walkable to Everything!
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (31 reviews)
"Excellent location and nice little house."
United States
Ann B.
The price is £374
includes taxes & fees
15 Nov - 16 Nov
Retreat in Historic Downtown Leesburg - Walkable to Everything!

4. 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 £411
includes taxes & fees
16 Nov - 17 Nov
Downtown Cottage with Fire Pit

5. 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, (79 reviews)
"Storybook Cottage was located perfectly for our 2 day trip for a friendship reunion and to explore Leesburg. Would definitely recommend!"
United States
Renee L.
The price is £400
includes taxes & fees
3 Dec - 4 Dec
Storybook cottage on Leesburg's most historic block — walk to everything

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)
"Great location in a great town!"
United States
Gigi D.
The price is £411
includes taxes & fees
18 Nov - 19 Nov
Historic Downtown Home with Fire Pit

7. 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 £417
includes taxes & fees
18 Nov - 19 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit

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 £433
includes taxes & fees
15 Nov - 16 Nov
Charming Cottage, Walk to Downtown, Porch Swings

9. Perfect 2-bedroom Treetop Bungalow Treehouse

Perfect 2-bedroom Treetop Bungalow Treehouse
Leesburg
10.0 out of 10, Exceptional, (3 reviews)
"Fun, creative place to stay. Worked well for our family of four for the weekend."
United States
Kathy S.
The price is £286
includes taxes & fees
24 Nov - 25 Nov
Perfect 2-bedroom Treetop Bungalow Treehouse

10. 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 £135
includes taxes & fees
29 Nov - 30 Nov
Stylish Studio with Kitchenette

11. The Cedars a local masterpiece in charming Poolesville

The Cedars a local masterpiece in charming Poolesville
Poolesville
10.0 out of 10, Exceptional, (1 review)
"The house was perfect for a weekend away with my finance and dog. We had a wedding in Potomac, and this house was the perfect location. Quiet back roads but only a few minutes to grocery stores and food options. Great backyard and fire pit. The host was super quick with communication. We would definitely stay here again."
United States
Hope A.
The price is £443
includes taxes & fees
17 Nov - 18 Nov
The Cedars a local masterpiece in charming Poolesville

12. 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
1 Dec - 2 Dec
super cosy cottage with high speed internet!

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 £938
includes taxes & fees
18 Nov - 19 Nov
Still Meadow Farm

14. 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, (10 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is £290
includes taxes & fees
16 Nov - 17 Nov
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

15. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery
Harpers Ferry
9.8 out of 10, Exceptional, (16 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 £241
includes taxes & fees
15 Nov - 16 Nov
Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery

16. 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 £360
includes taxes & fees
18 Nov - 19 Nov
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

17. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (23 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 £425
includes taxes & fees
16 Nov - 17 Nov
Spacious Modern Home on Middleburg Horse Farm

18. Dog-Friendly | Hiking| Tubing near Harpers Ferry

Dog-Friendly | Hiking| Tubing near Harpers Ferry
Brunswick
2.0 out of 10, (1 review)
"No ac just window units it was soooooo hot"
United States
Anonymous traveller
The price is £169
includes taxes & fees
17 Nov - 18 Nov
Dog-Friendly | Hiking| Tubing near Harpers Ferry

19. 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.
The price is £645
includes taxes & fees
15 Nov - 16 Nov
Hunters Retreat with High Speed Internet

20. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (75 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is £195
includes taxes & fees
15 Nov - 16 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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.

Learn more about Leesburg

Historic red-brick streets in city centre Leesburg lead to boutique shops and farm-to-table restaurants worth the drive. Visit nearby wineries along the foothills or explore Balls Bluff Battlefield where rangers point out Civil War trenches still visible today.

A large, yellow colonial-style building with white columns and shutters.

Top reviews in Leesburg