Upperville Vacation Rentals

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Vacation Rentals in Upperville

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"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

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

9.2 out of 10, Wonderful, (234)
"Nice cabin to relax and unwind. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

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.

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

9.0 out of 10, Wonderful, (7)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

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

10.0 out of 10, Exceptional, (55)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is CA $139
CA $504 total
includes taxes & fees
Sep 2 - Sep 3
Blue Ridge Getaway - Sunset Views, A.T. Access

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 $210
CA $444 total
includes taxes & fees
Sep 9 - Sep 10
Cottage on King | Charming Historic Leesburg Home

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 $139
CA $559 total
includes taxes & fees
Aug 28 - Aug 29
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"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

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>

Apple Mountain Retreat

10.0 out of 10, Exceptional, (14)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is CA $187
CA $324 total
includes taxes & fees
Aug 25 - Aug 26
Apple Mountain Retreat

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
9.8 out of 10, Exceptional, (6)
"Love the view and beautiful appointed decor throughout the home…"
The price is CA $224
CA $536 total
includes taxes & fees
Aug 27 - Aug 28
The Vue - Mountain top hot tub overlooking the Shenandoah River

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!

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

Silo Tiny House Cabin

9.2 out of 10, Wonderful, (5)
"Heated mattress was the best. Thank you! "
The price is CA $243
CA $411 total
includes taxes & fees
Aug 25 - Aug 26
Silo Tiny House Cabin

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 $381
CA $553 total
includes taxes & fees
Aug 26 - Aug 27
18th Century Stone Cottage minutes from historic Middleburg

Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

9.8 out of 10, Exceptional, (69)
"Communication with the host was excellent and an early check in was incredibly helpful - the house served its purpose exactly as expected - hosting friends for the weekend with easy access to the countryside of VA."
Where Charming Local History Meets Modern Comfort ~ Historic Fauquier County, VA

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 $197
CA $532 total
includes taxes & fees
Aug 27 - Aug 28
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Welcome to the Ladybug Retreat!

10.0 out of 10, Exceptional, (1)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
The price is CA $247
CA $566 total
includes taxes & fees
Sep 9 - Sep 10
Welcome to the Ladybug Retreat!

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (21)
"The property is well maintained. The surroundings are peaceful. It was conveniently located near the casino and winery we visited. The house only has one TV; but that gave us more time to make new memories. "
The price is CA $139
CA $603 total
includes taxes & fees
Aug 27 - Aug 28
The Oculus - Huge Cabin with a Hot Tub!

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Great stay for two young families. Lovely home and great location. Would recommend for a group trip to the area."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
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 Great Country Farms, 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.