Round Hill Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Round Hill vacation rentals

Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Jun 9 - Jun 10
Total with taxes and fees
The Pond Cabin
Apartment (1 Bedroom) | Interior

Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Near Loudoun Wine Trail: Apt w/ Restaurant On-site
3.0 star property
Hamilton
$309 nightly
The price is $352
Jun 7 - Jun 8
Total with taxes and fees
Near Loudoun Wine Trail: Apt w/ Restaurant On-site
House (3 Bedrooms) | Interior

Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
Walk to Stores: Home in Historic Shepherdstown!
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 Round Hill Hotel Reviews

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Great stay, close to our venue and staff was very accommodating!"
Kara 1-night trip
Posted 8 hours ago
Spark by Hilton Winchester

Find out more about Round Hill

Everything you need to know about Round Hill 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 Round Hill 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 Round Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Round Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Round Hill. 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 Round Hill 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 $141 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 Round Hill rentals

At Expedia, we put the best Round Hill 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 Round Hill 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 Round Hill 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 Round Hill. 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

Are there vacation rentals in Round Hill?

Yes, we have vacation rentals in Round Hill close to Round Hill Arts Center, or you can choose a more secluded option if you're looking for a relaxing stay. Round Hill is known for its golf courses and art.

What are some of the best vacation home rentals that Round Hill has to offer?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Round Hill offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Round Hill?

Choose from 6 Expedia vacation rentals in Round Hill for a memorable vacation.

What can I see and do in Round Hill?

Family-friendly attractions include Hill High Country Store and K & S Pewter, whereas Sleeter Lake is a spot to enjoy the outdoors. Stoneleigh Golf and Country Club and Round Hill Arts Center are other places to visit while you're in town.

What are vacation rentals like in Round Hill?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Round Hill. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family gatherings.