Upperville Holiday Rentals from AU$322: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Upperville has to offer?

Mountain View Bungalow in Front Royal : This holiday 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Upperville holiday rentals

A fenced grassy field with a clear sky and distant hills.

1. Lunar Loft, with mountain views

Bluemont

Christina C.

includes taxes & fees

21 Oct - 22 Oct

A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

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

Markham

Melissa B.

includes taxes & fees

25 Oct - 26 Oct

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

3. 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

Mary H.

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a porch, surrounded by trees and grass.

4. 1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

Erick U.

includes taxes & fees

17 Nov - 18 Nov

A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

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

Linden

David S.

includes taxes & fees

27 Oct - 28 Oct

A two-story house with a balcony, string lights, and a swing.

6. Cozy A frame cabin in quaint Front Royal. Dog friendly

Front Royal

Kye Y.

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

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

Front Royal

P H.

includes taxes & fees

3 Nov - 4 Nov

A hotel room with a bed, a dining table with chairs, a small table with a vase of flowers, and a storage unit with shelves.

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

Middleburg

Kathleen

includes taxes & fees

23 Oct - 24 Oct

A modern living room with a flat-screen TV, a sofa, a glass coffee table, and a wooden entertainment unit.

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

Front Royal

"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!"

Laura B.

includes taxes & fees

28 Oct - 29 Oct

A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

10. super cosy cottage with high speed internet!

Middleburg

Lynette

includes taxes & fees

21 Oct - 22 Oct

A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

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

Front Royal

Carla M.

includes taxes & fees

29 Oct - 30 Oct

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

12. Mountain home w/ hot tub & sunroom

Front Royal

Mollie S.

includes taxes & fees

3 Nov - 4 Nov

A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

13. Spacious Modern Home on Middleburg Horse Farm

Middleburg

Denise B.

includes taxes & fees

26 Oct - 27 Oct

A covered outdoor deck with a fire pit, seating, and a view of the landscape.

14. Mountain Cabin Retreat | Hot Tub & Foosball |

Front Royal

Christine T.

includes taxes & fees

3 Nov - 4 Nov

A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

15. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Fauquier County

Suzanne J.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a hot tub, steps, and a view of a forest.

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

Front Royal

Roland C.

includes taxes & fees

4 Nov - 5 Nov

A hot tub with a view of a forest and a sunset.

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

Linden

Scott M.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

18. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

Front Royal

casey p.

includes taxes & fees

9 Nov - 10 Nov

Local wineries, breweries, and small-town charm in Front Royal

19. Mountain Views w/Hot Tub, 95” TV & Trail Access

Shenandoah Farms

"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...

Joshua J.

includes taxes & fees

28 Oct - 29 Oct

A two-story house with a balcony, a hot tub, and a circular wooden structure.

20. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Front Royal

Charlie R.

includes taxes & fees

27 Oct - 28 Oct

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Upperville Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good

"Everything was good except, no towel racks in the bathroom. Room was clean , bed comfy. I will return."

Spark by Hilton Winchester

10/10 Excellent

"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"

Salamander Resort And Spa

10/10 Excellent

"The Salamander resort is breathtaking! Spectacular property. The staff was always willing to answer questions or to help in any way possible. Our room was clean and very comfortable. I was so happy to see that it is pet friendly. My only complaint was that guests left their dogs in their rooms while they were out. I heard a few dogs that were clearly distressed at being left alone. As a dog owner, it really upset me. The guests should be required to not leave their pets alone."

Find out more about Upperville

Everything you need to know about Upperville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Upperville holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upperville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upperville holiday rentals we have selected for you start as low as AU$322 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upperville rentals

At Expedia, we put the best Upperville holiday 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 holiday.

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.

Frequently asked questions

Can I find a holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

What are some of the best holiday rentals that Upperville has to offer?

Mountain View Bungalow in Front Royal: This holiday 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 holiday rentals are there in Upperville?

Choose from 7 Expedia holiday rentals in Upperville for a memorable holiday.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Great Country Farms, 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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upperville holiday rentals

1. Lunar Loft, with mountain views

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

3. 18th Century Stone Cottage minutes from historic Middleburg

4. 1910 Farmhouse on 6 Acres • VA Wine Country

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

6. Cozy A frame cabin in quaint Front Royal. Dog friendly

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

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

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

10. super cosy cottage with high speed internet!

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

12. Mountain home w/ hot tub & sunroom

13. Spacious Modern Home on Middleburg Horse Farm

14. Mountain Cabin Retreat | Hot Tub & Foosball |

15. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

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

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

18. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

19. Mountain Views w/Hot Tub, 95” TV & Trail Access

20. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Find holiday rentals that suit your style

Top Upperville Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

Quality Inn Winchester

Spark by Hilton Winchester

Travelodge by Wyndham Winchester

Salamander Resort And Spa

Red Roof Inn Leesburg, VA

Clarion Inn Harpers Ferry - Charles Town

Hotel Burg

Find out more about Upperville

Frequently asked questions

Go further with the Expedia app