Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Upperville vacation rentals

Exterior

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.
$323 nightly
The price is $360
Feb 1 - Feb 2
Total with taxes and fees
Lake View Retreat - Cottage Near a Peaceful Lake!
Interior

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, (30 reviews)
"Gorgeous cabin, incredibly clean and well stocked with everything needed. Hot tub was amazing and clean and huge. Greatful for the hosts promptness in communication.Thank you!"
United States
Samantha S.
$308 nightly
The price is $333
Feb 4 - Feb 5
Total with taxes and fees
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Terrace/patio

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
$329 nightly
The price is $363
Feb 4 - Feb 5
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Interior

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
$327 nightly
The price is $364
Feb 2 - Feb 3
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
Terrace/patio

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (1 review)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
$151 nightly
The price is $164
Feb 1 - Feb 2
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Property grounds

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
Front Royal
10.0 out of 10, Exceptional, (12 reviews)
"Our family had a lovely time at The Vue! It was clean, comfortable, and had everything we needed for a quick getaway. The mountain view was truly incredible and we enjoyed watching the sunrise with our coffee on the back deck. While there's not much of a yard, our pup enjoyed the outdoor space too! Thank for being a part of our family's special memories. We'll be back!"
United States
Alyssa L.
$347 nightly
The price is $383
Feb 9 - Feb 10
Total with taxes and fees
The Vue - Mountain Top hot tub overlooking the Shenandoah River
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (23 reviews)
"Lovely views, very spacious, well appointed in terms of kitchen."
United States
sharyn m.
$390 nightly
The price is $434
Feb 5 - Feb 6
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Fridge, microwave, oven, dishwasher

Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...
United States
Stacy H.
$372 nightly
The price is $414
Feb 10 - Feb 11
Total with taxes and fees
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Smart TV

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
10.0 out of 10, Exceptional, (16 reviews)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
$350 nightly
The price is $390
Feb 1 - Feb 2
Total with taxes and fees
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Outdoor spa tub

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.
$338 nightly
The price is $376
Feb 5 - Feb 6
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Living area

Wild Hare Cottage

Wild Hare Cottage
Purcellville
10.0 out of 10, Exceptional, (12 reviews)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
$193 nightly
The price is $220
Feb 4 - Feb 5
Total with taxes and fees
Wild Hare Cottage
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (13 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
$195 nightly
The price is $217
Feb 1 - Feb 2
Total with taxes and fees
Mountain View Bungalow in Front Royal
Dining

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (15 reviews)
"Everything was great! We had a lovely stay."
United States
Beth D.
$316 nightly
The price is $352
Feb 5 - Feb 6
Total with taxes and fees
Log Cabin w/ Hot Tub & Waterfront Patio!
Property grounds

Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Our family had a cozy weekend at the cabin. Tony was super helpful and a great host. Thank you for sharing your lovely property with us!"
United States
Katrina S.
$281 nightly
The price is $302
Feb 1 - Feb 2
Total with taxes and fees
Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Exterior

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (3 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$257 nightly
The price is $283
Feb 1 - Feb 2
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
Smart TV, fireplace

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

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (34 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
$350 nightly
The price is $390
Feb 1 - Feb 2
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
Terrace/patio

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful Sunsets, older cabin, not too steep of a drive up, outside deck is nice and fire pit area out front! Harper’s Ferry Area is cute and full of history! Be in shape to hike and climb while you are here, especially if you plan on doing a ghost walk after walking the town all day! 5 friends girls trip was great! "
United States
Teresa R.
$326 nightly
The price is $364
Feb 5 - Feb 6
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
Terrace/patio

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (9 reviews)
"We had a great stay "
United States
Lauren O.
$461 nightly
The price is $515
Feb 1 - Feb 2
Total with taxes and fees
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Property grounds

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.4 out of 10, Exceptional, (3 reviews)
"Property was very clean and accurate of listing description. cell phone service was rough however internet in house was never an issue. House is in good shape. Owner was quick to respond once receiving text message. Email is best way to communicate. you do have a lil drive into town if you need something however that was not an issue with us and the location is what we were looking for. Would 100% stay again if in the area"
United States
Kevin W.
$353 nightly
The price is $393
Feb 18 - Feb 19
Total with taxes and fees
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
TV, fireplace

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
Harpers Ferry
9.8 out of 10, Exceptional, (8 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
$327 nightly
The price is $365
Feb 1 - Feb 2
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Staff was very friendly and room was great! "
Courtney 3-night trip
Posted 3 days ago
Comfort Inn & Suites Winchester

Find out more about Upperville

Everything you need to know about Upperville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upperville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upperville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upperville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Upperville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $217 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upperville rentals

At Expedia, we put the best Upperville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upperville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upperville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upperville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

NEW! Ferrystone Lodge: Mountain Retreat w/ Patio & Fireplace: This vacation home rental outside of Upperville offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Upperville?

Choose from 5 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 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.