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

Upperville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Upperville vacation rentals

Exterior

1. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (66 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
$370 nightly
The price is $397
Sep 30 - Oct 1
Total with taxes and fees
18th Century Stone Cottage minutes from historic Middleburg
Property grounds

2. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.2 out of 10, Wonderful, (11 reviews)
"Beautiful, peaceful property. We originally lived in the area and were coming back to close out our business in town. The amenities in the home were great and everything was super clean. You definitely get the Northern Virginia rural experience here. Great location and hosts were amazing! Would stay here again!"
United States
Christina C.
$237 nightly
The price is $270
Sep 29 - Sep 30
Total with taxes and fees
Lunar Loft, with mountain views
Terrace/patio

3. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
$212 nightly
The price is $234
Oct 5 - Oct 6
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Property grounds

4. 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, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
$191 nightly
The price is $211
Sep 23 - Sep 24
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Exterior

5. 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, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$248 nightly
The price is $274
Sep 21 - Sep 22
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
TV, fireplace, offices

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

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$383 nightly
The price is $422
Sep 24 - Sep 25
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Exterior

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
$376 nightly
The price is $414
Sep 27 - Sep 28
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Outdoor dining

8. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
$247 nightly
The price is $265
Sep 27 - Sep 28
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Terrace/patio

9. Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6

Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
$391 nightly
The price is $431
Oct 5 - Oct 6
Total with taxes and fees
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Indoor spa tub

10. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Very quiet and private. The property was very clean, had all of the amenities needed. Very comfortable and homey. The only thing you need to be aware of is that the USPS does not deliver to the address, Amazon will have the post office hold it in Front Royal."
United States
Roland C.
$413 nightly
The price is $456
Sep 29 - Sep 30
Total with taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Desk, iron/ironing board, WiFi (free), bed sheets

11. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.6 out of 10, Exceptional, (29 reviews)
"The studio has potential but is not worth the price paid. Towels were old, mattress was soft, cobwebs were noticeable. Location is great."
United States
Kathleen
$239 nightly
The price is $272
Sep 24 - Sep 25
Total with taxes and fees
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Outdoor spa tub

12. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Front Royal
10.0 out of 10, Exceptional, (1 review)
"This beautifully new cabin in the mountains was the perfect getaway location! So serene and beautiful! The front porch and back deck areas were the perfect setting to catch up with family! We will definitely be booking again. Rex and Meredith communicated with us perfectly before and during our stay. The indoors were just as beautiful as the outside with gorgeous bathrooms and unbelievably comfortable beds! Even our pooch loved the getaway!"
United States
Laura B.
$319 nightly
The price is $352
Sep 22 - Sep 23
Total with taxes and fees
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Outdoor spa tub

13. 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
9.6 out of 10, Exceptional, (14 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.
$334 nightly
The price is $369
Sep 28 - Sep 29
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Exterior

14. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"We love this house. It was super quiet and cozy. The kitchen is the best stocked Vrbo kitchen we have ever encountered. If there is a drawback, I would say that it is the antique/original doorknobs. They do need to be repaired or replaced for ease of use. But on the other hand, no biggie and kind of add to the charm. We thoroughly enjoyed our stay!"
United States
Mark H.
$391 nightly
The price is $394
Sep 28 - Sep 29
Total with taxes and fees
1910 Farmhouse on 6 Acres • VA Wine Country
Coffee/tea maker, fridge, microwave, oven

15. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres
Loudoun County
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
$423 nightly
The price is $461
Sep 21 - Sep 22
Total with taxes and fees
DC Wine Country Farmhouse | 5 Peaceful Acres
Outdoor spa tub

16. Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge

Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
$432 nightly
The price is $470
Sep 22 - Sep 23
Total with taxes and fees
Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Outdoor dining

17. Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
$482 nightly
The price is $532
Sep 29 - Sep 30
Total with taxes and fees
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Terrace/patio

18. The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (23 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$357 nightly
The price is $394
Sep 22 - Sep 23
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Dining

19. Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (48 reviews)
"Very relaxing great time."
United States
Alfred A.
$320 nightly
The price is $356
Sep 21 - Sep 22
Total with taxes and fees
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Outdoor dining

20. Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views

Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
Front Royal
9.0 out of 10, Wonderful, (2 reviews)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
$324 nightly
The price is $357
Oct 5 - Oct 6
Total with taxes and fees
Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"The property was very clean the rooms very nice and the breakfast was nice and hot and included, unlimited bacon, which a lot of hotels I find don’t do that. The lady that took care of the breakfast was on point. They had bagels bread to make toast. They had a pancake machine that spit pancakes out like this was unbelievable delicious."
Belinda 1-night trip
Posted less than an hour ago
Microtel Inn & Suites by Wyndham 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 $211 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 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.