Round Hill vacation rentals

We found 168 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.

Vacation rentals with weekly discounts - Round Hill

Showing deals for:Apr 17 - Apr 24

Image gallery for Wild Hare Cottage

Exterior
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Wild Hare Cottage

Purcellville

9% off
Price is $216
$1,509 for 7 nights
All fees included
Wild Hare Cottage

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can immediately access member discounts and earn OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

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)
  • Doukenie Winery (6.2 mi / 10 km)
  • The Barns at Hamilton Station Vineyards (6.8 mi / 10.9 km)
  • 868 Estate Vineyards (7 mi / 11.2 km)
  • Breaux Vineyards (7.1 mi / 11.5 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)
  • Oatlands Historic House and Gardens (10.2 mi / 16.5 km)
  • Catoctin Valley (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)
  • Mackintosh Fruit Farm (15.3 mi / 24.6 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 when booking a vacation rental?
When considering a vacation rental in Round Hill, Virginia, a popular area to stay is the charming downtown area. This quaint neighborhood offers a mix of historical charm and modern amenities, making it a delightful base for your getaway. Within walking distance, you can explore local shops, cafes, and the picturesque Round Hill Park, which features walking trails and picnic areas, superb for enjoying the outdoors with family or friends.

Another appealing option is the countryside surrounding Round Hill, which boasts a variety of vacation rentals located among vineyards and rolling hills. This area provides a serene escape and is ideal for those looking to enjoy the natural beauty of Virginia. You can visit nearby wineries, such as those on the Loudoun Wine Trail, where you can sample local wines and take in stunning views. The countryside setting also offers opportunities for hiking and outdoor activities, making it a great choice for nature enthusiasts.

In terms of vacation rental options, the downtown area tends to have a cozy selection of properties, with several options available that cater to different group sizes and preferences. Similarly, the countryside around Round Hill features a range of rentals from charming cabins to spacious homes, allowing visitors to find the superb fit for their stay.
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 areas for renting a beach house in Round Hill?
For renting a beach house in Round Hill, Virginia, travelers should consider the charming waterfront areas along the nearby Potomac River and the scenic shores of the Chesapeake Bay. Although Round Hill itself is more inland, the nearby town of Lovettsville offers access to the riverfront, where visitors can find rental properties with picturesque views and direct access to water activities.

In the vicinity of Lovettsville, you can discover cozy vacation homes featuring amenities such as private docks, outdoor decks, and spacious yards ideal for barbecues and family gatherings. Many of these properties are equipped with full kitchens and comfortable living areas, making them superb for extended stays.

For a more beach-like experience, travelers may want to venture a bit further to the Chesapeake Bay area, particularly in towns like Colonial Beach. Here, beach houses often come with amenities like sandy beach access, outdoor showers, and fire pits, creating a superb setting for enjoying summer evenings by the water.
What is the most popular type of vacation rental accomodation in Round Hill?
In Round Hill, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the serene surroundings. Additionally, cottages and cabins are also commonly found, offering a charming and rustic experience that blends well with the natural beauty of the region. Many of these rentals provide amenities like fireplaces, BBQ grills, and proximity to local attractions such as hiking trails and vineyards, making Round Hill an appealing destination for travelers seeking a peaceful getaway. Apartments are also available, though they are less common, suiting those who prefer a more compact living space while still enjoying the area's tranquil ambiance.
Are there any family house rentals in Round Hill?
In Round Hill, Virginia, there are several family-friendly house rentals available, making it a delightful spot for groups looking to enjoy a peaceful getaway. The area is known for its scenic beauty and proximity to outdoor activities, particularly in the nearby Blue Ridge Mountains. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can safely play and explore.

Visitors can enjoy a variety of amenities such as fire pits for evening gatherings, cozy fireplaces for cooler nights, and some properties even include game rooms or basements with entertainment options. Additionally, Round Hill is conveniently located near local attractions, including hiking trails, wineries, and charming small-town shops, ensuring that there's something for everyone to enjoy during their stay.
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, making it an inviting destination for travelers with furry companions. Many of these vacation homes come equipped with amenities such as spacious backyards, cozy living rooms, and fully stocked kitchens, providing a comfortable home-away-from-home experience.

The area itself is surrounded by picturesque landscapes, with opportunities for outdoor activities that both pets and their owners can enjoy. Nearby parks and trails, such as the Appalachian Trail and local nature preserves, offer great spots for hiking and exploring with pets. Additionally, Round Hill's charming community features pet-friendly cafes and shops, allowing visitors to enjoy local flavors while spending time with their pets.
Are there any remote work vacation rentals in Round Hill?
In Round Hill, Virginia, there are several vacation rentals that cater to remote workers, with about 13 options available. These properties typically feature essential amenities for a productive work environment, including high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs. Additionally, many rentals offer safety features like in-room safes to secure personal belongings.

The scenic beauty of Round Hill, located in the foothills of the Blue Ridge Mountains, provides a tranquil backdrop for work and relaxation. Nearby, travelers can enjoy outdoor activities, including hiking trails and local parks, which add a refreshing escape when it's time to unwind. 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 WiFi, kitchens, and coffee/tea makers, making it convenient for guests to stay connected and prepare their own meals. Many rentals also boast mountain views, providing a picturesque backdrop to your stay. Additionally, some properties come equipped with blenders, great for those who enjoy making smoothies or other blended drinks during their vacation.
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 summer heat begins to fade and the fall foliage starts to emerge. This picturesque month offers a superb blend of comfortable temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, making it ideal for outdoor activities and sightseeing. Visitors can enjoy hiking along scenic trails in the nearby Blue Ridge Mountains or exploring local vineyards, which are particularly vibrant during this season.

The peak season in Round Hill generally spans from January to March, attracting those eager to experience winter sports and cozy getaways. This period sees an influx of visitors who enjoy skiing and snowboarding in nearby resorts, as well as the charming winter ambiance of the region.

For those looking for a more budget-friendly option, May offers a delightful time to visit without the crowds. The weather is typically mild, with temperatures ranging from the mid-50s to low 80s Fahrenheit. This month is superb for leisurely strolls through the vineyards or enjoying the blooming flowers in local parks, all while benefiting from lower rental rates.

Ultimately, the best time to book a vacation rental in Round Hill hinges on your preferences—whether you seek the vibrant energy of fall or the tranquility and savings of late spring.
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?
In Round Hill, Virginia, visitors can enjoy a quaint and picturesque setting surrounded by the Blue Ridge Mountains. The area is known for its outdoor attractions, including hiking trails and scenic views. Nearby, the Appalachian Trail offers numerous access points for hiking enthusiasts looking to explore the natural beauty of the region. For wine lovers, the Loudoun County Wine Trail features numerous vineyards and wineries, many of which are a short drive from Round Hill, making it an ideal spot for wine tastings and tours. The historic town of Middleburg, located not far from Round Hill, also offers charming shops, fine dining, and art galleries, enriching the experience for those staying in the area.
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.

More Vacation Ideas