Upperville Vacation Rentals

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Our top choices for Upperville vacation rentals

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (31 reviews)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is ¥30,151
¥37,633 total
includes taxes & fees
Mar 29 - Mar 30
Blue Mountain Cabin, secluded, perfect for couples, near main road

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (32 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is ¥32,783
¥54,811 total
includes taxes & fees
Apr 15 - Apr 16
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is ¥23,645
¥57,762 total
includes taxes & fees
Apr 14 - Apr 15
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.2 out of 10, Wonderful, (5 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
The price is ¥31,103
¥70,539 total
includes taxes & fees
Apr 13 - Apr 14
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is ¥21,423
¥34,972 total
includes taxes & fees
Mar 29 - Mar 30
Mountain View Bungalow in Front Royal

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (13 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is ¥35,705
¥62,233 total
includes taxes & fees
Mar 29 - Mar 30
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

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

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (66 reviews)
"Beautiful, secluded location. Well-organized check in/out process and guide for stay. Clean and well-stocked cabin made relaxing easy. Hosts were very friendly and helpful. We’ve already recommended this property to our friends! Perfect for a much-needed, cozy and relaxing vacation."
United States
Kheryssa P.
The price is ¥15,869
¥56,925 total
includes taxes & fees
Apr 13 - Apr 14
Blue Ridge Getaway - Sunset Views, A.T. Access

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (33 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
The price is ¥22,137
¥49,367 total
includes taxes & fees
Mar 29 - Mar 30
Leesburg Hideaway- King Bed + Private Backyard

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (85 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is ¥28,564
¥58,693 total
includes taxes & fees
Apr 6 - Apr 7
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is ¥36,657
¥76,840 total
includes taxes & fees
Apr 14 - Apr 15
The Foxwood Cabin | Hot Tub, Screened Porch, Grill

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
Lake View Retreat - Cottage Near a Peaceful Lake!

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (27 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is ¥31,738
¥72,367 total
includes taxes & fees
Mar 29 - Mar 30
Hidden Gem on Hidden Valley Lane

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
Harpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is ¥24,422
¥78,586 total
includes taxes & fees
Mar 31 - Apr 1
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"Great view, very secluded"
United States
Matt s.
The price is ¥15,939
¥59,299 total
includes taxes & fees
Apr 6 - Apr 7
Cottage w/ Hot Tub and 100-Mile Valley Views!

The River House

The River House
Charles Town
10.0 out of 10, Exceptional, (15 reviews)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is ¥25,708
¥54,951 total
includes taxes & fees
Mar 28 - Mar 29
The River House

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Harpers Ferry
9.0 out of 10, Wonderful, (11 reviews)
"Host was great - very communicative and made sure everything was perfect for our visit. Nice place and very clean. Enjoyed it very much!"
United States
William C.
The price is ¥37,438
¥63,006 total
includes taxes & fees
Mar 31 - Apr 1
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

4-bedroom cabin in enchanting Front Royal with AC

4-bedroom cabin in enchanting Front Royal with AC
Front Royal
The price is ¥30,849
¥75,335 total
includes taxes & fees
Mar 29 - Mar 30
4-bedroom cabin in enchanting Front Royal with AC

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is ¥25,390
¥51,636 total
includes taxes & fees
Mar 29 - Mar 30
Newly renovated Farm cottage with Mountain views

Dog-Friendly Cottage w Playground, Grill & Games

Dog-Friendly Cottage w Playground, Grill & Games
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
Dog-Friendly Cottage w Playground, Grill & Games

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is ¥25,530
¥51,863 total
includes taxes & fees
Mar 29 - Mar 30
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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

Find out more about Upperville

Search for holiday rentals in Upperville on Expedia! You can easily find your home rentals, villas, holiday apartments in Upperville using one of the methods below:

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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?

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

How many vacation rentals are there in Upperville?

Choose from 6 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 Virginia River Trips, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and RdV Vineyards 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.