Search Vacation Homes in Upperville
- 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 201 Vacation Homes in Upperville with updated reviews, rates, and availability.
![Exterior](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271141/6ea949fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Trailside Retreat in breathtaking Western Loudoun
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (43)
![Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft](https://images.trvl-media.com/lodging/84000000/83700000/83698500/83698458/782cfcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Charles Town Home w/ Private Pool & Hot Tub
Charles Town Home w/ Private Pool & Hot Tub
10.0 out of 10, Exceptional, (41)
![Outdoor spa tub](https://images.trvl-media.com/lodging/85000000/84140000/84136500/84136413/06558e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
10.0 out of 10, Exceptional, (33)
![Exterior detail](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/19d9567a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Cottage on King | Charming Historic Leesburg Home
Cottage on King | Charming Historic Leesburg Home
9.6 out of 10, Exceptional, (48)
The price is SAR 724
SAR 1,294 total
includes taxes & fees
3 Mar - 4 Mar
![Dining](https://images.trvl-media.com/lodging/102000000/101100000/101090800/101090756/beb595e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
10.0 out of 10, Exceptional, (22)
![Chester Gap Vacation Rental | 3BR | 2.5BA | 2 Stories | 1,400 Sq Ft](https://images.trvl-media.com/lodging/65000000/64610000/64605700/64605657/0bcc9fcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Modern Mountain Retreat w/ Deck + Hot Tub!
Modern Mountain Retreat w/ Deck + Hot Tub!
10.0 out of 10, Exceptional, (66)
![Gruner Bungalow](https://images.trvl-media.com/lodging/67000000/66700000/66697200/66697106/8d86f6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Gruner Bungalow at Otium Cellars
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (93)
![Exterior](https://images.trvl-media.com/lodging/33000000/32650000/32645500/32645481/af7ecce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Rural Home, Hot Tub, Campfire, Hardwood Floors
Rural Home, Hot Tub, Campfire, Hardwood Floors
9.4 out of 10, Exceptional, (71)
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 Upperville
![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (36)
The price is SAR 1,031
SAR 1,469 total
includes taxes & fees
17 Feb - 18 Feb
![Exterior](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/140d8a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
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, (244)
![Exterior](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271141/6ea949fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Trailside Retreat in breathtaking Western Loudoun
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (43)
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 Upperville hotels
Recent reviews of Upperville hotels
![La Quinta Inn & Suites by Wyndham Winchester](http://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)
La Quinta Inn & Suites by Wyndham Winchester
5/5 Excellent
"Clean room right off the Interstate with friendly staff and a better than normal breakfast. Perfect for a one night stay while traveling. "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 1 day 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 Upperville
- Cabin Rentals in Upperville
- Cottages in Upperville
- Apartments in Upperville
- B&B in Upperville
- Farmstay in Upperville
- Motels in Upperville
- Guest Houses in Upperville
- Chalets in Upperville
- Villas in Upperville
- Condo Rentals in Upperville
- Resorts in Upperville
- RV Parks in Upperville
- Inns in Upperville
- Hotels