Upperville Holiday Rentals

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Holiday 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 AU$525
includes taxes & fees
11 Aug - 12 Aug
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 AU$615
includes taxes & fees
12 Aug - 13 Aug
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 AU$510
includes taxes & fees
26 Aug - 27 Aug
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)
"Easy check-in, excellent communication. Home was very clean with quality furnishings and bedding. Lots of thoughtful touches and extras. Located along Shenandoah River makes it picturesque."
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 AU$370
includes taxes & fees
13 Aug - 14 Aug
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 AU$422
includes taxes & fees
12 Aug - 13 Aug
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 AU$751
includes taxes & fees
14 Aug - 15 Aug
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, (15)
"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 AU$597
includes taxes & fees
12 Aug - 13 Aug
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 AU$636
includes taxes & fees
21 Aug - 22 Aug
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!"
The price is AU$734
includes taxes & fees
24 Aug - 25 Aug
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 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 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 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.