A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Upperville Vacation Rentals

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Upperville vacation rentals

Exterior

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$401 nightly
The price is $442
Jul 15 - Jul 16
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Dining

~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, (93 reviews)
"This is a beautiful, clean, traquil and relaxing home away from home. The beds are comfortable, the living space is open and full of light during the day. The hosts have made great efforts to make this a family and/or couple friendly destination. Our dog was welcomed and enjoyed her stay (being with her people). The views are spectacular."
United States
Deb K.
$286 nightly
The price is $318
Jul 15 - Jul 16
Total with taxes and fees
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Smart TV, fireplace

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

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (72 reviews)
"We had a wonderful stay. Fantastic views from this cabin -- literally on top of the mountain. Hot tub was great, love the rocking chairs on the front porch, and really appreciate the games and "activites" in the house (like the basetball game in the basement). It was easy to bring our teenage boys and enjoy some down time for spring break. I'm sure the roads would be dicey in the winter but loved it and would definately stay there again."
United States
Jill R.
$331 nightly
The price is $368
Jul 15 - Jul 16
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
Outdoor dining

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (8 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
$325 nightly
The price is $362
Aug 2 - Aug 3
Total with taxes and fees
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Outdoor spa tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$329 nightly
The price is $362
Jul 15 - Jul 16
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
Leesburg Hideaway- King Bed + Private Backyard
Smart TV

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

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
$356 nightly
The price is $396
Jul 22 - Jul 23
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, (25 reviews)
"This was a lovely rental in a breathtaking location. My whole family gasped at that view as we came over the hill and down the driveway! Could not have asked for a more picturesque front yard, and the sunsets from the hot tub were epic. The house was very clean, comfortable, and well appointed, with two generously sized bath tubs inside and comfy beds. Great game selection (although some of the contents were mixed into the wrong boxes), and we enjoyed the ping pong table too. Communication...
United States
Lauren P.
$455 nightly
The price is $507
Jul 26 - Jul 27
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Property grounds

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, (37 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
$215 nightly
The price is $237
Jul 16 - Jul 17
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
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, (40 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
$353 nightly
The price is $394
Jul 21 - Jul 22
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
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
9.8 out of 10, Exceptional, (7 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
$378 nightly
The price is $421
Jul 16 - Jul 17
Total with taxes and fees
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
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
9.8 out of 10, Exceptional, (10 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
$165 nightly
The price is $184
Jul 20 - Jul 21
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Interior

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
$352 nightly
The price is $381
Jul 29 - Jul 30
Total with taxes and fees
Forest chalet w/ hot tub & BBQ grill
Outdoor dining

3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"While there was something left to be desired by the kitchen utensils and cookware, this place is located off the beaten path in a beautiful mountainside area. Definitely worth the price. Just bring your own pot holders and pizza cutter if you plan on having pizza lol. "
United States
Tyrell O.
$318 nightly
The price is $332
Jul 15 - Jul 16
Total with taxes and fees
3BR cabin w/ hot tub & game room
Property grounds

Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (33 reviews)
"Scott very responsive; gave us multiple recommendations for restaurants and places to see, things to do. My kids loved the hot tub, beds were very comfortable- we had a great time!"
United States
Katie F.
$220 nightly
The price is $244
Jul 16 - Jul 17
Total with taxes and fees
Mountain Cabin in the Woods, Near Wineries & More!
Fridge, oven, stovetop, dishwasher

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
$309 nightly
The price is $333
Jul 20 - Jul 21
Total with taxes and fees
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Property grounds

The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (4 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
$328 nightly
The price is $365
Jul 19 - Jul 20
Total with taxes and fees
The Blue Jay | New House in the Woods w/ Hot Tub
TV, fireplace, foosball, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (12 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
$392 nightly
The price is $433
Aug 5 - Aug 6
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (72 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
$384 nightly
The price is $427
Jul 22 - Jul 23
Total with taxes and fees
Terra Alta - Incredible River Views and Hot Tub!
Interior

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
Leesburg
8.8 out of 10, Excellent, (11 reviews)
"What an excellent stay! Ayda was an amazing host. The dome is very private and wonderfully outfitted. The hot tub was awesome and everything was clean and so comfy. In summer I can only imagine it is even more secluded as the trees leaf out!! Highly recommended and planning another stay. "
United States
Carter S.
$270 nightly
The price is $299
Jul 16 - Jul 17
Total with taxes and fees
Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
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

Salamander Resort And Spa

Salamander Resort And Spa

10/10 Excellent
"Very refreshing breakfast experience and the staff was great."
Wayne 1-night trip
Posted 9 hours ago
Salamander Resort And Spa

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 $220 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?

Mountain View Bungalow in Front Royal: This vacation home rental outside of Upperville offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Blue Ridge Regional Park, 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.