Upperville Vacation Rentals

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Upperville Vacation 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 CA $181
CA $417 total
includes taxes & fees
Aug 5 - Aug 6
Cottage on King | Charming Historic Leesburg Home
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)
"Our stay at Bala’s home was wonderful. The location right on the river is perfect for a relaxing getaway. A very close drive to the National Park and Front Royal. The home is updated nicely and amenities are well stocked, above average kitchen supplies from the typical vacation rental. Do note that there are no tvs in the bedrooms which we appreciated but some may not. Overall it was great. "
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (256)
"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
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)
"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
Outdoor dining

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!
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Interior

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

9.8 out of 10, Exceptional, (6)
"The property is beautiful and just outside of Front Royal. We visited local vineyards and hit the skyline drive on the way home. We loved relaxing in the GeoDome home!"
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
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!
Kalia’s Mountain Momma Getaway
Dining tables

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (9)
"Location was nice"
The price is CA $150
CA $244 total
includes taxes & fees
Aug 5 - Aug 6
Kalia’s Mountain Momma Getaway
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (52)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
Fridge, microwave, oven, stovetop

Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.

7.6 out of 10, Good, (25)
"Easy check in. House is located in a cluster of homes. Photos are misleading. Cleanliness was sub par. Linens and towels from previous guests were laying on top of the washer. Wasn’t sure if the linens and towels that we did have were even clean and fresh. Home smelled of alcohol and cigarettes. Good location."
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
Mountain Getaway - 7 beds (2 King) - Large Common Area
Terrace/patio

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (13)
"Great place to stay for a family wedding. House was exactly how it was in the photographs. "
Mountain Getaway - 7 beds (2 King) - Large Common Area
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

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

9.6 out of 10, Exceptional, (95)
"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 CA $197
CA $598 total
includes taxes & fees
Aug 13 - Aug 14
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Fridge, microwave, oven, stovetop

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (14)
"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."
The price is CA $196
CA $526 total
includes taxes & fees
Aug 26 - Aug 27
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Lakefront House w/ Modern Comforts!
Property grounds

Lakefront House w/ Modern Comforts!

9.0 out of 10, Wonderful, (2)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
The price is CA $215
CA $593 total
includes taxes & fees
Aug 6 - Aug 7
Lakefront House w/ Modern Comforts!
Main Street U.S.A. - Walk to Everything
Bar (on property)

Main Street U.S.A. - Walk to Everything

8.0 out of 10, Very good, (2)
"Location was perfect, the beds were very comfortable, and the house was lovely. The host was responsive and the check in/out couldn’t be easier. Two of the bedrooms and one of the bathrooms are accessed by passing through another bedroom which is a little awkward depending on who you are staying with. "
Main Street U.S.A. - Walk to Everything
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Property grounds

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

10.0 out of 10, Exceptional, (14)
"Wonderful hosts and a great home! Lots of extra special touches."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.
Fridge, microwave, oven, stovetop

Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.

7.4 out of 10, Good, (3)
"A delightful home that has plenty of room to run and play outside. Tucked into the woods, but surrounded by lots of open grass around the house with a fire pit and even room for a volleyball net or other activities. Great hot tub on the screened in patio, easy to get to, close to Front Royal, quiet property, lovely place to relax and super nice host! "
The price is CA $307
CA $553 total
includes taxes & fees
Aug 6 - Aug 7
Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Dining

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (31)
"Beautiful, well-maintained home. Definitely hope to return! "
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Property grounds

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

9.8 out of 10, Exceptional, (58)
"We stayed for 3 days and loved it. The garden was beautiful and loved seeing the cows!"
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Pet-Friendly Berryville Home: Walk to Main Street!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Berryville Home: Walk to Main Street!

9.4 out of 10, Exceptional, (19)
"The property was very nice and well kept. It was a nice cozy time. "
Pet-Friendly Berryville Home: Walk to Main Street!
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
Sign in
Sign up, it's free

Top Upperville Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Everyone was so nice, from the lobby staff to the restaurant...definitely will be returning"
Anonymous traveller 1-night trip
Posted 1 day ago
Holiday Inn Winchester Se-Historic Gateway by IHG