Photo by Stephanie Sutton
Search Vacation Homes in Middleburg
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 255 Vacation Homes in Middleburg with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (44)

1805 Farmhouse with Heated Pool in Harpers Ferry
1805 Farmhouse with Heated Pool in Harpers Ferry
10.0 out of 10, Exceptional, (37)

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
9.8 out of 10, Exceptional, (47)

Historic Hideaway
Historic Hideaway
10.0 out of 10, Exceptional, (14)
The price is SAR 563
SAR 1,191 total
includes taxes & fees
19 Mar - 20 Mar

Modern Home on Middleburg Equestrian Farm
Modern Home on Middleburg Equestrian Farm
10.0 out of 10, Exceptional, (11)

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
10.0 out of 10, Exceptional, (9)
The price is SAR 525
SAR 1,325 total
includes taxes & fees
13 Mar - 14 Mar

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
10.0 out of 10, Exceptional, (6)

Gruner Bungalow at Otium Cellars
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (95)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (38)
The price is SAR 1,032
SAR 1,489 total
includes taxes & fees
20 Mar - 21 Mar

Global Luxury Suites at Reston Town Center
Global Luxury Suites at Reston Town Center
8.2 out of 10, Very Good, (126)
The price is SAR 513
SAR 1,004 total
includes taxes & fees
16 Mar - 17 Mar

Breathtaking views with an indoor private pool, come escape with us
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (246)
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.
Recent reviews of Middleburg hotels
Recent reviews of Middleburg hotels

Courtyard by Marriott Dulles Airport Herndon
5/5 Excellent
"Convenient location."
A verified traveler stayed at Courtyard by Marriott Dulles Airport Herndon
Posted 6 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Middleburg
- Apartments in Middleburg
- Cabin Rentals in Middleburg
- Cottages in Middleburg
- Farmstay in Middleburg
- B&B in Middleburg
- Villas in Middleburg
- Guest Houses in Middleburg
- Chalets in Middleburg
- Condo Rentals in Middleburg
- Motels in Middleburg
- Resorts in Middleburg
- Aparthotels in Middleburg
- RV Parks in Middleburg
- Houseboats in Middleburg
- Inns in Middleburg
- Residences in Middleburg
- Hotels