Round Hill vacation rentals

We found 179 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Round Hill that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as parking and a fireplace. At the end of the day, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

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Find out more about Round Hill

Why visit Round Hill

  • Outdoor Adventures: Round Hill is a paradise for nature lovers, featuring scenic hiking trails and beautiful parks.
  • Historical Charm: Explore local historic houses that offer a glimpse into the fascinating past of the area.
  • Romantic Getaways: The quaint atmosphere makes Round Hill perfect for couples seeking a relaxing retreat.
  • Family-Friendly Activities: Enjoy a variety of attractions that cater to families, ensuring fun for all ages.
  • Cozy Accommodations: Choose from charming cottages, rustic cabins, or private vacation homes for a comfortable stay.

Popular types of accommodation in Round Hill

If you’re planning a getaway to Round Hill, you’ll find a variety of cozy accommodations to suit your needs. The most popular options include houses, charming cottages, and rustic cabins. Whether you're searching for houses for rent in Round Hill or VA rentals, we have the perfect options to ensure your stay is comfortable and enjoyable. Discover your ideal Round Hill home away from home today.

  • Houses: The top choice for travelers in Round Hill, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A delightful option, these quaint homes provide a cozy atmosphere, ideal for a peaceful getaway.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats blend comfort with the great outdoors.
  • Apartments: A convenient choice for those seeking an urban vibe, combining comfort with accessibility.
  • Condos: Offering modern amenities, these stylish units are great for a relaxed stay with easy access to local attractions.**

Top attractions in and around Round Hill

Round Hill, Virginia, is perfect for outdoor lovers and those seeking a romantic getaway. Visitors can explore urban parks, historic houses, and nature reserves, offering a blend of culture and family-friendly experiences. Whether you’re hiking in scenic landscapes or enjoying the charm of local history, Round Hill has something for everyone, ensuring an unforgettable vacation.

  • Round Hill Arts Center: Immerse yourself in the local arts scene at Round Hill Arts Center, where you can explore various exhibitions, attend workshops, and enjoy the vibrant cultural atmosphere that celebrates creativity.
  • Shenandoah Lake Beach: Relax and unwind at Shenandoah Lake Beach, a beautiful spot for swimming, sunbathing, and picnicking, surrounded by scenic views and a tranquil environment just 6 miles from Round Hill.
  • Morven Park: Discover the rich history of Morven Park, an elegant historic estate featuring stunning gardens, a museum, and guided tours, located 11 miles from Round Hill, perfect for history enthusiasts.

Things to do recommended for couples

For a romantic getaway in Round Hill, visit Bluemont Vineyard for a cozy wine tasting experience, catch a show at Tally Ho Theatre for live entertainment, and indulge in luxury at Sleepy Hollow Country Club. Each spot offers a unique vibe for couples to enjoy together.

Things to do recommended for families

Families can have a blast at Fireman's Field for sports excitement, enjoy arcade games at the Panther Family Fun Center, or unwind at Upperville Park for some relaxation. Each spot offers a unique vibe, perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a day at Stoneleigh Golf and Country Club for some outdoor sports, browse unique items at K & S Pewter, and unwind with friends at B-Chord Brewery, where you can savor great brews in a romantic atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Round Hill

If you're traveling with friends, family, pets, or planning an extended stay, be sure to focus on the right priorities when filtering your options. Here are some helpful booking tips for Vrbo.

  • Traveling to Round Hill with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for gatherings. Thankfully, you can easily filter for these and many other options on Vrbo.
  • Traveling to Round Hill with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Round Hill: For many families, a vacation isn't truly fulfilled without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Round Hill: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on long-term rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Round Hill

Round Hill, Virginia, offers a delightful blend of outdoor adventures and romantic getaways. Nestled in the scenic Catoctin Valley, this charming town is surrounded by friendly neighborhoods that invite you to explore family-friendly activities and historical sites. Whether you're hiking in nature or enjoying local entertainment, Round Hill promises a relaxing atmosphere perfect for creating lasting memories on your vacation.

  • Harpers Ferry: Nestled approximately 13 miles from Round Hill, Harpers Ferry is a charming city that offers a rich blend of outdoor adventure and scenic beauty. Visitors flock to this historic town for its stunning views and recreational opportunities. The area is a paradise for outdoor enthusiasts, featuring trails for hiking, skiing, and exploring the nearby national and state parks. Key attractions include the Harpers Ferry National Historical Park, where history and nature converge, and the picturesque Potomac and Shenandoah rivers, perfect for kayaking and fishing.
  • Leesburg: Located just 11 miles from Round Hill, Leesburg is a vibrant city that caters to families and city explorers alike. With a mix of modern amenities and historic charm, Leesburg offers a delightful travel experience. Shop at the local shopping mall and recreational areas, or immerse yourself in the city’s history by visiting its historic houses and event venues. Don’t miss the serene landscapes of the nearby national state park, which provide opportunities for picnicking and outdoor activities, making it a perfect family destination.
  • Purcellville: Only 3 miles from Round Hill, Purcellville is a quaint city that exudes a laid-back charm, ideal for those seeking outdoor experiences and scenic vistas. This small yet inviting town is surrounded by beautiful landscapes and offers various recreational activities. Visitors can enjoy shopping at local centers or explore the nearby national and state parks, which are perfect for hiking and enjoying nature. With its welcoming atmosphere and proximity to outdoor adventures, Purcellville is a hidden gem worth exploring.

Best time to go to Round Hill

If you're planning a trip to Round Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January to February and September, while off-peak times, like April to May and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.4°F (0.2°C)Light RainMostly SunnySlightly HighSlightly Low
February35.6°F (2.0°C)Light RainMostly SunnySlightly HighSlightly Low
March43.2°F (6.2°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly LowAverage
May63.3°F (17.4°C)Light RainMostly SunnySlightly LowAverage
June71.8°F (22.1°C)Light RainMostly SunnyAverageAverage
July77.0°F (25.0°C)Light RainMostly SunnyAverageSlightly High
August74.8°F (23.8°C)Light RainMostly SunnyAverageAverage
September68.2°F (20.1°C)Light RainMostly SunnySlightly HighAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageSlightly High
November44.8°F (7.1°C)Light RainMostly SunnyAverageSlightly High
December37.6°F (3.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your next adventure? Being flexible with your travel dates can really pay off, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, or review and organize your bookings. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The artsy city of Round Hill awaits you

Enjoy the art galleries and other features of Round Hill. One of the city's many top draws is its golfing. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Round Hill

Are you looking for attractions to visit in the area? Venture out of your vacation home and experience everything that makes Round Hill a fun spot to vacation. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Stoneleigh Golf and Country Club (1 mi / 1.6 km)
  • Bluemont Vineyard (4.3 mi / 7 km)
  • 8 Chains North Winery (6.4 mi / 10.2 km)
  • 868 Estate Vineyards (7 mi / 11.2 km)
  • Breaux Vineyards (7.1 mi / 11.5 km)
  • Stone Tower Winery (8.6 mi / 13.9 km)

Exploring the natural landscape of Round Hill

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Round Hill is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Shenandoah Lake Beach (5.9 mi / 9.5 km)
  • Blue Ridge Regional Park (6.1 mi / 9.7 km)
  • Glenwood Park (8.8 mi / 14.2 km)
  • Oatlands Historic House and Gardens (10.2 mi / 16.5 km)
  • Blue Ridge Center for Environmental Stewardship (11.4 mi / 18.3 km)
  • Aldie Mill Historic Park (12.8 mi / 20.6 km)

Transportation options to and around Round Hill

The nearest airport is in Washington Dulles Intl. Airport (IAD), located 21.2 mi (34.1 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 22.3 mi (35.9 km) away.

Frequently asked questions

What is the best area to stay in Round Hill, Virginia, United States of America when booking a vacation rental?
When considering a vacation rental in Round Hill, Virginia, a popular area to stay is the charming neighborhood surrounding the historic downtown area. This quaint community offers a delightful blend of scenic beauty and small-town charm, making it a great base for your getaway. You'll find several vacation rental properties in this area, suiting various preferences and group sizes.

One of the top attractions nearby is the historic Round Hill Town Center, where you can explore local shops and enjoy delicious dining options. Additionally, the proximity to the stunning Blue Ridge Mountains provides ample opportunities for outdoor activities such as hiking, biking, and enjoying breathtaking views.

Another popular point of interest is the nearby Loudoun Valley Vineyards, which offers wine tastings and tours, great for those looking to sample the local flavors.
How much does it cost to rent a vacation home in Round Hill?
Prices for vacation rentals in Round Hill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Round Hill to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Round Hill vacation house rentals?
You can find great discounts on house rentals in Round Hill on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Round Hill ski resort rentals?
For those seeking ski resort rentals near Round Hill, Virginia, the closest skiing options can be found in the nearby Blue Ridge Mountains, particularly at resorts like Wintergreen and Massanutten, which are a short drive away. In the vicinity of these resorts, travelers can find cozy cabins and lodge-style accommodations that cater to winter sports enthusiasts. Many of these properties feature amenities such as fireplaces, spacious living areas, and fully equipped kitchens, great for relaxing after a day on the slopes.

In the Wintergreen area, for instance, you can discover vacation homes that offer stunning mountain views and easy access to ski lifts. Many rentals here come with additional features like hot tubs, outdoor decks, and proximity to hiking trails for those who want to explore the natural beauty of the region when the snow melts.

Similarly, the Massanutten resort area provides a variety of lodging options, from ski-in/ski-out condos to larger family homes. These accommodations typically include access to resort amenities such as indoor water parks, fitness centers, and dining options, enhancing the overall experience for travelers.
What is the most popular type of vacation rental accomodation in Round Hill?
In Round Hill, vacation houses are quite prevalent, with several available throughout the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the scenic views of the Virginia countryside. Many also include amenities such as fireplaces and large living areas, making them ideal for families or groups seeking a comfortable retreat. Additionally, there are several cottages and cabins that provide a charming, rustic experience, often located in nature, offering cozy atmospheres and outdoor seating options. Apartments are also available, typically located in convenient areas, providing essential amenities for travelers looking for a more compact stay.
Are there any family house rentals in Round Hill?
In Round Hill, Virginia, there are several family-friendly house rentals available, offering a great base for exploring the scenic beauty of the area. Properties in this region typically feature spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces for children to enjoy. Many homes also include amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.

The town's proximity to attractions like the beautiful Blue Ridge Mountains provides ample opportunities for outdoor adventures, including hiking and picnicking. Visitors can also explore the charming local community and its offerings, making this area a wonderful choice for families seeking a memorable getaway.
Can I find long-stay vacation rentals in Round Hill?
A long-stay vacation rental in Round Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Round Hill?
In Round Hill, Virginia, there are several pet-friendly house rentals available for travelers looking to enjoy the area's natural beauty with their furry companions. These vacation homes often come equipped with amenities such as spacious backyards, modern kitchens, and cozy living spaces, making them suitable for families or groups. Many properties provide easy access to local parks and hiking trails, allowing pets to enjoy the outdoors alongside their owners.

The surrounding area boasts charming landscapes and outdoor activities, with opportunities for hiking, biking, and exploring nature. The proximity to the Blue Ridge Mountains ensures that visitors can enjoy scenic views and fresh air, making Round Hill an excellent choice for those seeking a pet-friendly getaway.
Are there any remote work vacation rentals in Round Hill?
In Round Hill, Virginia, there are several remote work vacation rentals available, making it a great choice for those looking to balance work and leisure. Many of these properties feature essential amenities for remote work, including reliable internet access and dedicated workspaces equipped with desks and comfortable chairs. Additionally, travelers can expect complimentary Wi-Fi in their rooms to facilitate smooth connectivity.

The charming town is surrounded by the natural beauty of the Virginia countryside, offering opportunities for outdoor activities during breaks. Rentals often provide spacious living areas where guests can relax after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Round Hill vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Round Hill with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Round Hill?
In Round Hill, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature cozy fireplaces, providing a warm and inviting atmosphere, especially during cooler months. Air conditioning is commonly available to ensure comfort during the warmer seasons. Additionally, travelers can expect to find books for leisurely reading and coffee or tea makers for that great morning beverage.
When is the best time to visit Round Hill for a vacation rental?
September is the most popular time to visit Round Hill, Virginia, as the vibrant fall foliage begins to emerge, creating a picturesque setting for outdoor activities and exploration. During this month, the weather is typically mild, with temperatures ranging from the low 50s to mid-70s Fahrenheit, making it ideal for hiking the scenic trails or enjoying leisurely strolls through the charming town.

The peak season in Round Hill runs from January to March, when winter sports enthusiasts flock to the nearby mountains for skiing and snowboarding. While this is a bustling time for those seeking winter adventures, September offers a serene alternative with fewer crowds and a focus on enjoying the natural beauty of the area.

For travelers looking for a more budget-friendly option, May is an excellent time to visit. During this month, you can enjoy the blooming landscape and pleasant temperatures without the high tourist activity of the summer and winter months. This allows for a more relaxed experience as you explore the local wineries or take in the scenic views.
How early should I book a Round Hill vacation rental?
Book your Round Hill vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Round Hill, Virginia, United States of America?
In Round Hill, Virginia, visitors can enjoy a variety of attractions that highlight the area's natural beauty and rich history. The town is located near the scenic Blue Ridge Mountains, providing ample opportunities for outdoor activities such as hiking, biking, and enjoying breathtaking views. Nearby, the Appalachian Trail offers a chance for adventurous travelers to explore the region's stunning landscapes.

For wine enthusiasts, the Loudoun County Wine Trail features numerous wineries and vineyards in the surrounding area, where visitors can partake in tastings and tours to sample local wines. The historic town of Middleburg, just a short drive away, is known for its charming boutiques, art galleries, and equestrian culture, making it a delightful day trip.

Additionally, Round Hill's proximity to the Catoctin Creek offers opportunities for fishing, canoeing, and enjoying serene waterside picnics.
Can I change or cancel my Round Hill home rental booking on Vrbo?
To find Round Hill vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Round Hill vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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