Upperville Vacation Rentals

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Vacation Rentals in Upperville

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

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

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (90)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

9.4 out of 10, Exceptional, (3)
"The apartment is great. I suspect it would be particularly awesome for a long-term stay. It's a basement apartment, so stairs weren't a surprise. Obviously, if you're not mobile, you won't pick this apartment. However, if you're a little wobbly, the stairs only have one handrail (it's not sketchy, but I rely pretty heavily on my handrails, and this one was not comforting), the bathroom floor is shiny and terrifying, the walk to the unit is bumpy, with lots of tree roots, uphill, and possibly...
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (36)
"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

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

9.2 out of 10, Wonderful, (232)
"Quiet, cozy cabin in serene setting. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

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

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (46)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is CA $379
CA $543 total
includes taxes & fees
Aug 5 - Aug 6
18th Century Stone Cottage minutes from historic Middleburg

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (46)
"We had a nice stay at this location. The property managers were extremely quick to respond and helpful pointing out must visit locations while at the property."
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

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

10.0 out of 10, Exceptional, (2)
"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 CA $137
CA $455 total
includes taxes & fees
Aug 25 - Aug 26
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

Wild Hare Cottage

10.0 out of 10, Exceptional, (6)
"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"
The price is CA $193
CA $327 total
includes taxes & fees
Aug 6 - Aug 7
Wild Hare Cottage

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

9.8 out of 10, Exceptional, (17)
"Great two days at the farm. Quiet, clean, and friendly hosts. :) "
The price is CA $207
CA $372 total
includes taxes & fees
Aug 5 - Aug 6
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Modern Mountain Retreat w/ Deck + Hot Tub!

9.8 out of 10, Exceptional, (74)
"Very comfortable and spacious place with all the comforts of home. We wanted to get away and just relax for a few days and this was perfect!"
Modern Mountain Retreat w/ Deck + Hot Tub!

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 CA $277
CA $666 total
includes taxes & fees
Aug 11 - Aug 12
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

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

10.0 out of 10, Exceptional, (14)
"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 CA $221
CA $525 total
includes taxes & fees
Aug 11 - Aug 12
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

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 CA $138
CA $561 total
includes taxes & fees
Aug 21 - Aug 22
Terra Alta - Incredible River Views and Hot Tub!

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

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (54)
"Perfect house for a trip to the mountains!"
Blue Ridge Getaway - Sunset Views, A.T. Access
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 Upperville Hotel Reviews

Frequently asked questions

Can I find a vacation rental in Upperville?

Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

What are some of the best vacation home rentals that Upperville has to offer?

Breathtaking View with an Indoor Pool: This vacation home rental outside of Upperville is located in the mountains and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Upperville?

Choose from 4 Expedia vacation rentals in Upperville for a memorable vacation.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Blue Ridge Regional Park, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

What are vacation rentals like in Upperville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.