Upperville Holiday Rentals

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Holiday Rentals in Upperville

Our top choices for Upperville holiday rentals

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 AU$570
includes taxes & fees
4 Sept - 5 Sept
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 AU$500
includes taxes & fees
9 Sept - 10 Sept
Cottage on King | Charming Historic Leesburg Home

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is AU$637
includes taxes & fees
1 Sept - 2 Sept
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, (15)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is AU$368
includes taxes & fees
24 Aug - 25 Aug
Apple Mountain Retreat

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

Wild And Wonderful Silos

9.2 out of 10, Wonderful, (5)
"Heated mattress was the best. Thank you! "
The price is AU$466
includes taxes & fees
25 Aug - 26 Aug
Wild And Wonderful Silos

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

The price is AU$2,859
includes taxes & fees
2 Sept - 3 Sept
Grand 9BR Provenance Manor Ideal for Weddings & Gatherings

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 AU$619
includes taxes & fees
4 Sept - 5 Sept
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."
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

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 AU$692
includes taxes & fees
4 Sept - 5 Sept
The Oculus - Huge Cabin with a Hot Tub!

Lakefront Log Cabin w/ Dreamy Waterfront Patio!

2.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful property. Nice views of the lake."
The price is AU$510
includes taxes & fees
4 Sept - 5 Sept
Lakefront Log Cabin w/ Dreamy Waterfront Patio!

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 holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

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

Breathtaking View with an Indoor Pool: This holiday home rental outside of Upperville is located in the mountains, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Upperville?

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

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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.