Search Vacation Homes in Upperville

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Upperville

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is SAR 547
SAR 1,190 total
includes taxes & fees
24 Jun - 25 Jun
Cottage on King | Charming Historic Leesburg Home

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

9.8 out of 10, Exceptional, (96)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
The price is SAR 2,211
SAR 4,094 total
includes taxes & fees
3 Jul - 4 Jul
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (29)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is SAR 601
SAR 1,213 total
includes taxes & fees
18 Jun - 19 Jun
Newly renovated Farm cottage with Mountain views

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (11)
"Great place, very relaxing"
Cozy Country Getaway in the Heart of Upperville

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (17)
"We had a great time "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

A unique mountaintop getaway overlooking Willow Croft Winery.

10.0 out of 10, Exceptional, (97)
"Clean and nice place to stay. Prompt communication from the owners. "
The price is SAR 1,182
SAR 2,229 total
includes taxes & fees
17 Jun - 18 Jun
A unique mountaintop getaway overlooking Willow Croft Winery.

The PINK PEARL in Historic Leesburg

9.4 out of 10, Exceptional, (36)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg

Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

10.0 out of 10, Exceptional, (13)
"Everything was wonderful!"
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (48)
"The houses wonderfully decorated and super clean. Has many amenities. It’s very convenient if you’re visiting Leesburg. Lots of awesome restaurants in the general vicinity and interesting historical sites."
Trailside Retreat in breathtaking Western Loudoun

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!

Charles Town Townhome: 9 Mi to Harpers Ferry

10.0 out of 10, Exceptional, (11)
"Enjoyed a 3 night stay. Nice neighborhood convenient to Harper's Ferry. Property was as described."
Charles Town Townhome: 9 Mi to Harpers Ferry

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (7)
"Location was nice"
The price is SAR 409
SAR 664 total
includes taxes & fees
17 Jun - 18 Jun
Kalia’s Mountain Momma Getaway

6 Bedroom Farmhouse Owned by Bear Chase

10.0 out of 10, Exceptional, (68)
"House was amazing. Spacious, clean, and had everything we needed. Especially enjoyed the game room and ample kitchen space (on main and third floor). Highly recommend staying here! "
6 Bedroom Farmhouse Owned by Bear Chase

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"Multiple generations enjoyed this lovely house with plenty of space, well stocked kitchen, and great location for winery visits. Highlights include extra sleeping space, local coffee provided by the host, and the hottub! Gorgeous views and responsive hosy! "
The price is SAR 375
SAR 1,520 total
includes taxes & fees
24 Jun - 25 Jun
Terra Alta - Incredible River Views and Hot Tub!

Mountain Chic Retreat-Harpers Ferry, Appalachian Trail & Wine country!

The price is SAR 434
SAR 1,314 total
includes taxes & fees
17 Jun - 18 Jun
Mountain Chic Retreat-Harpers Ferry, Appalachian Trail & Wine country!

New - Modern Mountain Retreat w/ Hot tub and view!

10.0 out of 10, Exceptional, (20)
"This is a very comfortable and spacious house with beautiful mountain views. We had a great time here!"
New - Modern Mountain Retreat w/ Hot tub and view!

Nature Escape | Pond, Dock, Fire Pit, Trails

Nature Escape | Pond, Dock, Fire Pit, Trails

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (92)
"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"
The price is SAR 672
SAR 1,792 total
includes taxes & fees
26 Jun - 27 Jun
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Pet-Friendly Berryville Home: Walk to Main Street!

9.4 out of 10, Exceptional, (16)
"Great stay! Lovely home. Host was very helpful! Would highly recommend!"
Pet-Friendly Berryville Home: Walk to Main Street!

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

10.0 out of 10, Exceptional, (9)
"Wonderful hosts and a great home! Lots of extra special touches."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
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