Upperville Holiday Rentals

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Holiday Rentals in Upperville

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

10.0 out of 10, Exceptional, (1)
"Didn’t know what to expect, but regardless I was blown away. The place is VERY well furnished with everything you need to enjoy your stay. It was the perfect place to come back home to and relax after a long day. The owner was also amazing, she left a few chocolates and a welcome note. She was also an amazing communicator, I didn’t need too many things, but the things I did need, she accommodated instantly. 10/10, this place is phenomenal "
The price is NZ$549
includes taxes & fees
24 June - 25 June
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

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

10.0 out of 10, Exceptional, (42)
"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, (43)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is NZ$665
includes taxes & fees
24 June - 25 June
18th Century Stone Cottage minutes from historic Middleburg

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 NZ$564
includes taxes & fees
9 July - 10 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, (228)
"Very nice accommodations "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

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 NZ$660
includes taxes & fees
26 June - 27 June
Secluded Cabin a Stone's Throw From the A.T.!

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

8.8 out of 10, Excellent, (18)
"We had a great time "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (96)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (7)
"Location was nice"
The price is NZ$296
includes taxes & fees
24 June - 25 June
Kalia’s Mountain Momma Getaway

Cozy studio close to Skyline Drive, Hiking, and Main Street.

9.0 out of 10, Wonderful, (2)
"Spent the day in the park , very convenient "
Cozy studio close to Skyline Drive, Hiking, and Main Street.

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (85)
"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, (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, (69)
"The cabin was very nice and quaint. We had a nice stay. The view from the sunroom is great amazing. The place is very cozy and made for a great night away. "
The price is NZ$611
includes taxes & fees
1 July - 2 July
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Apple Mountain Retreat

10.0 out of 10, Exceptional, (13)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is NZ$407
includes taxes & fees
24 June - 25 June
Apple Mountain Retreat

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

9.8 out of 10, Exceptional, (27)
"So much to do in the area, cute little cottage, very clean and comfortable "
The price is NZ$1,176
includes taxes & fees
2 July - 3 July
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

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 NZ$1,377
includes taxes & fees
1 July - 2 July
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Wild Hare Cottage

10.0 out of 10, Exceptional, (4)
"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 NZ$392
includes taxes & fees
2 July - 3 July
Wild Hare Cottage

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

10.0 out of 10, Exceptional, (16)
"Just exceptional. Perfectly located for adventure. "
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (18)
"This was a great place for our vacation."
The price is NZ$729
includes taxes & fees
7 July - 8 July
The Oculus - Huge Cabin with a Hot Tub!

6 Bedroom Farmhouse Owned by Bear Chase

10.0 out of 10, Exceptional, (68)
"House was amazing. Spacious, clean, and had everything we needed. Especially enjoyed the game room and ample kitchen space (on main and third floor). Highly recommend staying here! "
6 Bedroom Farmhouse Owned by Bear Chase
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 Dinosaur Land, 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.