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Holiday Homes in Middleburg

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Middleburg and around

Our top choices for Middleburg holiday homes

Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is €262
includes taxes & fees
9 Sept - 10 Sept
Cottage on King | Charming Historic Leesburg Home
Luxury Home at One Loudoun
Fridge, microwave, oven, stovetop

Luxury Home at One Loudoun

9.2 out of 10, Wonderful, (17)
"We really enjoyed our stay! The property was just what we needed, and the host was very accommodating—allowing us to check in early, which was immensely appreciated after a long drive. There are a lot of stairs, but we considered it our vacation workout! Would definitely stay again!"
The price is €386
includes taxes & fees
1 Sept - 2 Sept
Luxury Home at One Loudoun
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (98)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

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

10.0 out of 10, Exceptional, (4)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
The price is €285
includes taxes & fees
8 Sept - 9 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
A unique mountaintop getaway overlooking Willow Croft Winery.
Terrace/patio

A unique mountaintop getaway overlooking Willow Croft Winery.

10.0 out of 10, Exceptional, (103)
"The perfect 3 bed/3.5 bath new build cabin for a get away with friends or family. We have nothing negative to say about this property. Our stay was Amazing."
The price is €525
includes taxes & fees
2 Sept - 3 Sept
A unique mountaintop getaway overlooking Willow Croft Winery.
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

9.0 out of 10, Wonderful, (7)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "
Breathtaking View with an Indoor Pool
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Outdoor dining

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

10.0 out of 10, Exceptional, (2)
"Easy check-in, excellent communication. Home was very clean with quality furnishings and bedding. Lots of thoughtful touches and extras. Located along Shenandoah River makes it picturesque."
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Terrace/patio

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

10.0 out of 10, Exceptional, (13)
"We appreciate everything from the discrete location,hot tub and many accommodations. What a PERFECT home to stay away from home while we explored the trails and history of the surrounding area. Great eats and trails only minutes away! "
The price is €362
includes taxes & fees
24 Aug - 25 Aug
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Terrace/patio

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (15)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is €371
includes taxes & fees
26 Aug - 27 Aug
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Property grounds

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

9.8 out of 10, Exceptional, (58)
"Beautiful property and grounds. Setting was quiet and peaceful. Would stay again."
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Linden Family Home w/ Yard < 5 Mi to Wineries!
TV, books

Linden Family Home w/ Yard < 5 Mi to Wineries!

2.0 star property
8.6 out of 10, Excellent, (12)
"Great place to stay on a nice mountain my family and dogs loved itMike was great and answered any questions we had will definitely book again in the future"
Linden Family Home w/ Yard < 5 Mi to Wineries!
Aeris Suite
Interior

Aeris Suite

8.6 out of 10, Excellent, (4)
"Great visit. Would definitely stay again."
The price is €181
includes taxes & fees
25 Aug - 26 Aug
Aeris Suite
Terra Alta - Incredible River Views and Hot Tub!
Exterior

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is €356
includes taxes & fees
1 Sept - 2 Sept
Terra Alta - Incredible River Views and Hot Tub!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Fridge, microwave, oven, stovetop

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (45)
"The home is super clean and well maintained! "
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (57)
"This is a great place for a large group or family. Lots of beds. Large table for dining. Great backyard for running"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
Outdoor dining

Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

9.8 out of 10, Exceptional, (69)
"Communication with the host was excellent and an early check in was incredibly helpful - the house served its purpose exactly as expected - hosting friends for the weekend with easy access to the countryside of VA."
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA
6 Bedroom Farmhouse Owned by Bear Chase
Interior

6 Bedroom Farmhouse Owned by Bear Chase

10.0 out of 10, Exceptional, (76)
"Beautiful property! House was perfect!"
6 Bedroom Farmhouse Owned by Bear Chase
Historic and Updated Farmhouse Built in 1808
Terrace/patio

Historic and Updated Farmhouse Built in 1808

10.0 out of 10, Exceptional, (141)
"We really enjoyed our visit and stay at this house. It is close enough to the metro station and Leesburg, but away from the development. We would definitely stay here again."
Historic and Updated Farmhouse Built in 1808
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

Hyatt Regency Dulles

Hyatt Regency Dulles

10/10 Excellent
"Perfect "
Fahmi 1-night trip
Posted 2 days ago
Hyatt Regency Dulles