Upperville Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Upperville

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
Fridge, microwave, oven, stovetop

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 ￥14,500
￥47,525 total
includes taxes & fees
Jun 24 - Jun 25
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg
18th Century Stone Cottage minutes from historic Middleburg
Exterior

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 ￥39,875
￥57,568 total
includes taxes & fees
Jun 24 - Jun 25
18th Century Stone Cottage minutes from historic Middleburg
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Terrace/patio

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

9.2 out of 10, Wonderful, (227)
"Very nice accommodations "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

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

9.2 out of 10, Wonderful, (17)
"We had a great time "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (85)
"Property was very well equipped and close to vineyards and great places to eat. Highly recommend for a relaxing and fun experience."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Property grounds

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>
Secluded Cabin a Stone's Throw From the A.T.!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (23)
"Such a lovely gem in a gorgeous setting. Perfect for a girls weekend getaway. We plan to book again for this trip next year!"
The price is ￥14,500
￥57,107 total
includes taxes & fees
Jun 26 - Jun 27
Secluded Cabin a Stone's Throw From the A.T.!
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (42)
"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
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

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 ￥19,488
￥44,754 total
includes taxes & fees
Jun 24 - Jun 25
Cottage on King | Charming Historic Leesburg Home
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Private kitchen

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 "
The price is ￥24,715
￥31,068 total
includes taxes & fees
Jun 22 - Jun 23
Cozy studio close to Skyline Drive, Hiking, and Main Street.
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

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!"
The price is ￥85,629
￥159,636 total
includes taxes & fees
Jul 3 - Jul 4
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Smart TV, DVD player, books, video library

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 ￥22,897
￥50,705 total
includes taxes & fees
Jun 23 - Jun 24
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Smart TV, fireplace, video-game console, Netflix

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 ￥73,853
￥91,883 total
includes taxes & fees
Jun 22 - Jun 23
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Newly renovated Farm cottage with Mountain views
Outdoor dining

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (29)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is ￥23,200
￥46,861 total
includes taxes & fees
Jun 24 - Jun 25
Newly renovated Farm cottage with Mountain views
Mountain Chic Retreat-Harpers Ferry, Appalachian Trail & Wine country!
Exterior

Mountain Chic Retreat-Harpers Ferry, Appalachian Trail & Wine country!

The price is ￥19,285
￥54,039 total
includes taxes & fees
Jun 24 - Jun 25
Mountain Chic Retreat-Harpers Ferry, Appalachian Trail & Wine country!
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Bar (on property)

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

9.8 out of 10, Exceptional, (26)
"So much to do in the area, cute little cottage, very clean and comfortable "
The price is ￥46,420
￥97,544 total
includes taxes & fees
Jul 2 - Jul 3
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Apple Mountain Retreat
Property grounds

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 ￥20,880
￥35,186 total
includes taxes & fees
Jun 24 - Jun 25
Apple Mountain Retreat
Kalia’s Mountain Momma Getaway
Dining tables

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (7)
"Location was nice"
The price is ￥15,805
￥25,648 total
includes taxes & fees
Jun 20 - Jun 21
Kalia’s Mountain Momma Getaway
6 Bedroom Farmhouse Owned by Bear Chase
Interior

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
Breathtaking View with an Indoor Pool
Outdoor dining

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (252)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
Breathtaking View with an Indoor Pool
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 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?

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people: This vacation 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 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 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.