Upperville Holiday Rentals from €191: Search Short-Term Rentals

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

Breathtaking View with an Indoor Pool : This holiday home rental outside of Upperville is located in the mountains, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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Our top choices for Upperville holiday rentals

Cozy cabin w/hot tub & game room

Harpers Ferry

"Tony always answered my texts immediately and was very easy to work with. The place was just as expected; it was comfortable and all amenities were available. Towels were laid out on the beds and the comforters were cute and cozy. The place is well worn; some appliances, mostly gas stove and microwave and towel hooks were very worn out but still useable. We loved all of the amenities, space and privacy in this cabin. We would stay here again. "

Jenifer D.

includes taxes & fees

20 Apr - 21 Apr

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

Harpers Ferry

Colleen J.

includes taxes & fees

21 Apr - 22 Apr

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

Front Royal

Wafaa L.

includes taxes & fees

20 Apr - 21 Apr

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

Linden

Scott M.

includes taxes & fees

5 May - 6 May

Log Cabin w/ Hot Tub & Waterfront Patio!

Harpers Ferry

Nicole H.

includes taxes & fees

20 Apr - 21 Apr

Cabin at the Gap | You Won't Believe the View!

Harpers Ferry

Hidden Gem on Hidden Valley Lane

Linden

Lisa W.

includes taxes & fees

20 Apr - 21 Apr

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

Stephens City

Chris F.

includes taxes & fees

21 Apr - 22 Apr

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Top Upperville Hotel Reviews

Red Roof Inn Leesburg, VA

8/10 Good

"Easy place to stay,no frills type place! Easy parking and close by food,carry out,sit down."

La Quinta Inn & Suites by Wyndham Winchester

6/10 Okay

"The breakfast was the worst I have EVER had! The “scrambled eggs” were not real. They were egg beaters—- horrible, dry, tasteless. The “biscuits were even worse. They were the consistency of compressed sawdust and tasted worse! The hard boiled eggs had GREY yolks! One bite and I was horrified. Breakfast must (like all other meals) MUST BE FRESH, AND FRESHLY MADE! Although we have another reservation at your hotel on the way home, we will not be eating the breakfast unless it is real freshly bought, and freshly prepared. If it is not, we will never stay at your hotel again."

Sleep Inn & Suites Winchester near University

6/10 Okay

"This property has been on a steady decline. 1st floor ice maker has been "out of order" for over a year now. Remote power button didn't work, toilet seat shifted, chair in the room was leaning to one side as if it could break at any wrong move. Children had stayed in this room, and Stickers were stuck in the carpet. What was once a fair priced decent place to stay, has become a property in need of renovations. Call Pam Ellis & Associates for all your hotel renovations needs!"

Clarion Inn Harpers Ferry - Charles Town

6/10 Okay

"The bathroom was not clean on arrival- dirty sink, trash not empty, empty tissue box - the decaf and hot water at the breakfast set up were not hot - in fact I suspect the decaf coffee was stored overnight in the fridge - it wasn’t room temp -it was ice cold. The main restaurant was very slow - there was one other table when we arrived and it took 20 minutes for the food to arrive. The waitress said there was only 1 cook - I was a professional chef -I’ve served over 180 people in one dinner shift by myself"

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, apart-hotels, 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 favorite 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 depends 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 €191 per night. Entering your travel dates in the search wizard you might find 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?

Breathtaking View with an Indoor Pool: This holiday home rental outside of Upperville is located in the mountains, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Upperville?

Choose from 6 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 Dinosaur Land, 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 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.

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