Round Hill holiday rentals

We found 188 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Round Hill that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Round Hill

Showing deals for:25 Dec - 1 Jan

15' tall Holiday tree will be up from Thanksgiving to late January. It really is a sight to see!
The deck features ~900 sq ft from the master bedroom to the kitchen and panoramic views of the vineyard and opposing ridge line. Comfortable seating for the whole group!
Welcome to your cooking retreat - Thermador Column Fridge and Freezer, Gas Stove, Huge Kitchen Sink, Coffee and Hot Coco Station and an Austrian Tile Stove
Pool features a connected hot-tub with waterfall into the pool BUT the best feature is the view
Exceptional
(60 reviews)

Vinewood Estate Luxury Pool and Vineyard Retreat

Purcellville

8% off
AU$20,005
for 7 nights, 1 chalet
AU$2,858 per night
includes taxes & fees
Vinewood Estate Luxury Pool and Vineyard Retreat
Gather and enjoy meals in the spacious, fully stocked kitchen.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
Stream your favorite TV shows and movies with high-speed internet.
The Kitchen Nook offers additional seating, and a cozy place to read.
Exceptional
(6 reviews)

The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm

Waterford

8% off
AU$5,150
for 7 nights, 1 room
AU$736 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
Exterior
Living area
Private kitchen
Living area
Exceptional
(30 reviews)

Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly

Round Hill

21% off
AU$10,978
for 7 nights, 1 home
AU$1,568 per night
includes taxes & fees
Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly
Outdoor dining
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Front of cottage, French doors on left lead to stone patio
Interior
Exceptional
(113 reviews)

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704

Leesburg

16% off
AU$4,198
for 7 nights, 1 home
AU$600 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Outdoor dining
Open concept kitchen
Fully stocked kitchen
Exterior
Exceptional
(5 reviews)

Sunset Lion Mountain Cabin near a Lake & Vineyards

Harpers Ferry

8% off
AU$4,401
for 7 nights, 1 cabin
AU$629 per night
includes taxes & fees
Sunset Lion Mountain Cabin near a Lake & Vineyards
Living area
Terrace/patio
Interior
Dining
Exceptional
(46 reviews)

Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues

Bluemont

8% off
AU$4,953
for 7 nights, 1 home
AU$708 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Kitchen
Springtime at The Cottage
Welcome
Fire Pit
Exceptional
(119 reviews)

A Restored Wagon Barn On A 1790's Farm.

Purcellville

8% off
AU$2,544
for 7 nights, 1 cottage
AU$363 per night
includes taxes & fees
A Restored Wagon Barn On A 1790's Farm.
Interior
Property grounds
Exterior
Property grounds
Exceptional
(26 reviews)

Historic Mountain Cottage at Blue Ridge Overlook

Bluemont

8% off
AU$5,122
for 7 nights, 1 home
AU$732 per night
includes taxes & fees
Historic Mountain Cottage at Blue Ridge Overlook
Living area
Property grounds
Private kitchen
My home from the road.
Exceptional
(13 reviews)

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

8% off
AU$2,445
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

The arty 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 holiday 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 top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that Round Hill has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Stone Tower Winery (8.6 mi / 13.9 km)

Exploring the natural landscape of Round Hill

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Round Hill is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah Lake Beach (5.9 mi / 9.5 km)
  • Glenwood Park (8.8 mi / 14.2 km)
  • Oatlands Historic House and Gardens (10.2 mi / 16.5 km)
  • Aldie Mill Historic Park (12.8 mi / 20.6 km)
  • Ashburn Park (16.2 mi / 26 km)
  • Shenandoah River (26 mi / 41.9 km)

Transport options to and around Round Hill

The nearest airport is in Washington Dulles International Airport (IAD), located 21.2 mi (34.1 km) from the city centre. 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 most popular type of holiday rental accomodation in Round Hill?
In Round Hill, the most popular type of holiday rental accommodation is holiday houses, with around 16 available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, making them ideal for families and larger groups. Additionally, there are approximately 12 cottages that provide a charming and rustic experience, often located in scenic locations that allow guests to immerse themselves in nature. For those seeking a more compact option, several apartments and cabins are also available, offering comfortable living spaces with essential amenities.
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 choice for those travelling with children. The area is known for its scenic beauty and proximity to outdoor activities, offering a range of properties that cater to families. Many of these homes provide spacious living areas, full kitchens for preparing meals together, and outdoor spaces where kids can play or enjoy a barbecue.Nearby, visitors can explore local attractions such as the breathtaking views of the Blue Ridge Mountains and the tranquil waters of the Potomac River, great for outdoor adventures like hiking and fishing. Families can also take advantage of the area's parks, which often feature playgrounds and picnic areas, ideal for a day out in nature.
Are there any remote work holiday rentals in Round Hill?
In Round Hill, Virginia, there are numerous holiday rentals that cater to remote workers, with around 36 options available. This charming area is known for its picturesque landscapes and tranquil environment, making it an ideal setting for those looking to balance work and relaxation. Many of these properties come equipped with essential amenities such as free Wi-Fi, providing a reliable connection for remote work.Travellers can expect a variety of accommodations, from spacious homes with dedicated office spaces to cosy cabins that offer a peaceful retreat. The nearby countryside offers scenic views and outdoor activities, providing an excellent backdrop for breaks from work. Round Hill's local attractions, including parks and trails, enhance the experience, allowing for refreshing escapes into nature after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Round Hill?
In Round Hill, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals with ease. Many properties also feature cosy fireplaces, superb for creating a warm and inviting atmosphere during cooler evenings. Air conditioning is commonly available, ensuring comfort during the warmer months. Additionally, rentals often provide a selection of books for leisurely reading, along with coffee and tea makers for those who enjoy a hot beverage at any time of day.
When is the best time to visit Round Hill for a holiday rental?
September is the most popular time to visit Round Hill, Virginia, as the summer heat begins to wane, ushering in the beautiful autumn season. This month is particularly appealing for those who appreciate outdoor activities, such as hiking and wine tasting, with comfortable temperatures typically ranging from 10 to 25 degrees Celsius. As the leaves start to change, the scenic beauty of the Blue Ridge Mountains becomes a stunning backdrop for exploration.The peak season in Round Hill generally spans from January to March, when winter sports enthusiasts flock to the area for activities like skiing and snowboarding. This season is vibrant with visitors enjoying the crisp mountain air and the charm of the nearby wineries, all while indulging in the region's rich offerings.For those looking for a more budget-friendly experience, May is a lovely option. This month falls outside the high tourist season, providing a tranquil atmosphere superb for leisurely exploration of the local trails and vineyards without the crowds. You can savour the beauty of spring blooms while enjoying the warmth of the sun, making it a delightful time for outdoor pursuits.
What are the top attractions in Round Hill?
In Round Hill, Virginia, visitors can enjoy a range of attractions that highlight the area's natural beauty and historical significance. The town is located in the scenic Loudoun County, making it an ideal base for exploring the surrounding countryside and vineyards. Nearby, you can find the quaint village of Hillsboro, which features charming shops and the historic Hillsboro Community Centre.Outdoor enthusiasts will appreciate the proximity to the Appalachian Trail, which offers excellent hiking opportunities with stunning views of the Blue Ridge Mountains. Additionally, the area is known for its wineries, such as those along the Loudoun Wine Trail, where visitors can sample local wines and enjoy picturesque vineyard landscapes.For a taste of local history, the Round Hill Historic District offers a glimpse into the town's past, with several preserved buildings and sites that reflect its heritage.
Are all fees included in the Round Hill holiday homes prices shown on Stayz?
Stayz 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.
Are there any Round Hill holiday homes with parking?
Stayz offers a wide selection of holiday homes in Round Hill with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Round Hill holiday homes?
You can find great discounts on holiday homes in Round Hill on Stayz, 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.
Can I change or cancel my Round Hill holiday home booking on Stayz?
To find Round Hill holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Round Hill?
A long-stay holiday home in Round Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Round Hill holiday home?
Book your Round Hill holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Round Hill?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Round Hill to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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