Upperville Holiday Rentals

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Holiday Rentals in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (86)
"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.

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is AU$486
includes taxes & fees
7 July - 8 July
Cottage on King | Charming Historic Leesburg Home

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

9.2 out of 10, Wonderful, (229)
"Quiet, cozy cabin in serene setting. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

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

10.0 out of 10, Exceptional, (43)
"Great getaway location. Beautiful property"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (44)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AU$611
includes taxes & fees
7 July - 8 July
18th Century Stone Cottage minutes from historic Middleburg

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (253)
"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

Secluded Cabin a Stone's Throw From the A.T.!

9.8 out of 10, Exceptional, (24)
"We had an amazing time staying in this beautiful home. Communication and pre-trip information was outstanding, and the house was exactly as described. We didn’t even need to leave the property, we had everything we needed right there. Loved seeing a wild turkey and a baby deer with its mama, and the view from the kitchen and dining area was so serene. We would definitely stay here again!"
The price is AU$600
includes taxes & fees
7 July - 8 July
Secluded Cabin a Stone's Throw From the A.T.!

Escape to Shenandoah River, Hot Tub after a Hike!

10.0 out of 10, Exceptional, (47)
"We had a great overnight stay. The house was very clean, and the hot tub was a nice bonus!"
The price is AU$648
includes taxes & fees
9 July - 10 July
Escape to Shenandoah River, Hot Tub after a Hike!

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

9.0 out of 10, Wonderful, (2)
"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...
The price is AU$517
includes taxes & fees
7 July - 8 July
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (7)
"Location was nice"
The price is AU$273
includes taxes & fees
7 July - 8 July
Kalia’s Mountain Momma Getaway

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (43)
"The PERFECT stay! We came for the Upperville horse show and you cannot beat the location of this charming cottage. Close proximity to dining, grocery stores, wineries, horse show, and on a quiet street. William was an excellent host with attention to detail, thoughtfulness, and quick and responsive to any questions. "
Historical cottage in the town of Paris

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (71)
"The cabin was beautiful! Brigid has the cabin well stocked. She was very welcoming. Our family with kids and a dog felt very comfortable and even pampered!"
The price is AU$540
includes taxes & fees
10 July - 11 July
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

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

10.0 out of 10, Exceptional, (51)
"Our stay was perfect "
The price is AU$561
includes taxes & fees
7 July - 8 July
Blue Ridge Getaway - Sunset Views, A.T. Access

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (19)
"This was a great place for our vacation."
The price is AU$671
includes taxes & fees
7 July - 8 July
The Oculus - Huge Cabin with a Hot Tub!

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Cozy 1-bedroom apartment with WiFi, AC in awesome Warrenton

8.0 out of 10, Very good, (1)
"Check in was seamless. Property was in good condition. We were only there to sleep so we didn't take advantage of the amenities but it would have been very convenient to cook or relax. Only reason for four stars was it could have been cleaner. There was random hair in all the places you'd normally store things, there was no temperature control that we could find and we looked everywhere. Didn't want to disturb the hosts when we got back after 10 pm to go to sleep but it was absolutely freezing....
The price is AU$232
includes taxes & fees
7 July - 8 July
Cozy 1-bedroom apartment with WiFi, AC in awesome Warrenton

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 AU$360
includes taxes & fees
16 July - 17 July
Wild Hare Cottage

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

10.0 out of 10, Exceptional, (5)
"Great hidden gem, something very cool and special about this place, highly recommend!!"
The price is AU$1,045
includes taxes & fees
10 July - 11 July
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

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

7.8 out of 10, Good, (24)
"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

10.0 out of 10, Exceptional, (11)
"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
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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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?

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people: This holiday home rental outside of Upperville offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.