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Hillsboro vacation rentals

We found 307 vacation rentals — enter your dates for availability

Nestled in the heart of Virginia's picturesque countryside, Hillsboro beckons with its charming village atmosphere, historic landmarks, and stunning natural surroundings. Explore vibrant urban parks, engage in outdoor adventures, or visit the local farmers market to savor fresh regional produce. Ideal for families and groups, our cozy vacation rentals—including rustic cabins and inviting cottages—offer the perfect blend of comfort and convenience, ensuring a memorable home-away-from-home experience as you discover all Hillsboro has to offer.

Holiday rentals with weekly discounts - Hillsboro

Showing deals for:Oct 30 - Nov 6

Image gallery for Vinewood Estate: private spa, vineyard

Everything you could want for a fun family or friend getaway! Multiple firepits, Lots of seating on the deck and around the pool.
10 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)

Vinewood Estate: private spa, vineyard

Hillsboro

9% off
Price is $1,527
$10,688 for 7 nights
All fees included
Vinewood Estate: private spa, vineyard

Find spaces that suit your style

Find out more about Hillsboro

Why visit Hillsboro

  • Outdoor Adventures: Enjoy hiking trails and nature reserves perfect for exploration and relaxation.
  • Historic Sites: Discover the rich history of Hillsboro through its charming local landmarks.
  • Family-Friendly Activities: Engage in fun excursions suitable for families and kids.
  • Local Entertainment: Catch a game or event at the Hillsboro Stadium for an exciting local experience.
  • Charming Accommodations: Choose from cozy cottages and rustic cabins for a perfect home away from home.

Popular types of accommodation in Hillsboro

Discover the charm of Hillsboro with our selection of vacation rentals, including houses, cozy cottages, and rustic cabins. Whether you're seeking family-friendly hotels or unique properties in Hillsboro, we have options to suit every traveler’s needs. Enjoy transparency, savings, and peace of mind as you plan your getaway in this vibrant community. Start your adventure today and find the perfect home away from home.

  • Houses: These spacious and fully-equipped homes are the top choice for visitors to Hillsboro, offering comfort and privacy for families, friends, or couples.
  • Cottages: Quaint and charming, cottages provide a cozy atmosphere, making them the second favorite for those seeking a unique stay in the area.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic escape and are the third most booked option by travelers.
  • Apartments: Convenient and often centrally located, apartments are the fourth most popular choice for a comfortable urban stay.
  • Villas: Luxurious and spacious, villas are the fifth most sought-after accommodations, perfect for a lavish getaway.**

Top attractions near Hillsboro

Hillsboro, Virginia, is perfect for outdoor and romantic getaways, offering a blend of urban parks, historic sites, and nature reserves. Explore local points of interest, ideal for families and culture enthusiasts alike. Consider excursions around Hillsboro, discover the best vacation ideas, and find top vacation rentals within your budget. Don't miss a visit to the Hillsboro Stadium for some local entertainment.

  • Harpers Ferry National Historical Park: A rich tapestry of American history, this park features stunning landscapes, Civil War sites, and vibrant culture. Explore historic buildings and trails while soaking in the natural beauty of the confluence of the Potomac and Shenandoah Rivers.
  • Shenandoah Lake Beach: A perfect spot for relaxation and recreation, this beach offers sandy shores, swimming, and picnicking. Enjoy the serene atmosphere and the picturesque views of the surrounding mountains.
  • Morven Park: This historic estate showcases beautiful gardens, an impressive mansion, and engaging exhibits. Experience the rich cultural heritage and enjoy outdoor activities in a serene setting.

Things to do recommended for couples

For a romantic getaway in Hillsboro, visit Breaux Vineyards for a cozy wine tasting just 2 miles away, or enjoy a show at Tally Ho Theatre, 10 miles distant. For a touch of luxury, unwind at Sleepy Hollow Country Club, located 9 miles from Hillsboro.

Things to do recommended for families

Families visiting Hillsboro can enjoy the energetic atmosphere at Fireman's Field, a sports facility only 5 miles away. For a more relaxing experience, Elizabeth Mills Riverfront Park and Kephart Bridge Landing, located 15 miles away, offers beautiful scenery and a chance to unwind together.

Things to do recommended for groups

In Hillsboro, groups can shop at the Leesburg Corner Premium Outlets for a variety of brands and enjoy the vibrant atmosphere. For thrill-seekers, head to Summit Point Motorsports Park for an adrenaline-fueled racing experience. Don't miss K & S Pewter for unique local crafts just a short drive away.

*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 Hillsboro

If you're traveling with a group, with family, bringing your pets, or seeking extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Hillsboro with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Hillsboro with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding 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 Hillsboro: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Hillsboro: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Hillsboro

Hillsboro, Virginia, offers a charming escape perfect for outdoor adventures and romantic getaways. Explore the friendly atmosphere of nearby towns, ideal for family fun and entertainment. With numerous vacation homes available, visitors can enjoy excursions into the beautiful Highland County, rich in history and natural beauty. From hiking trails to quaint local shops, Hillsboro and its surroundings promise an unforgettable experience for every traveler.

  • Harpers Ferry: Nestled 9 miles from Hillsboro, Harpers Ferry is a charming city known for its rich history and stunning natural beauty. Set at the confluence of the Potomac and Shenandoah Rivers, visitors are drawn to its outdoor adventures and scenic landscapes. Explore the scenic trails of the Harpers Ferry National Historical Park, go hiking, or take part in thrilling activities like skiing during the winter months. With picturesque views and a vibrant atmosphere, Harpers Ferry is an ideal destination for nature lovers and adventure seekers alike.
  • Leesburg: Located 10 miles from Hillsboro, Leesburg offers a delightful blend of family-friendly activities and urban charm. This historic city is perfect for a day of exploration, featuring a variety of shopping centers, recreational areas, and local dining options. Don’t miss the chance to visit historic sites such as the local historic houses and the nearby national state park. With its vibrant community events and picturesque surroundings, Leesburg is an excellent choice for visitors looking to enjoy outdoor experiences and family fun.
  • Charles Town: Just 10 miles from Hillsboro, Charles Town boasts a romantic and adventurous atmosphere. Known for its lively entertainment scene, the city features a popular racetrack and various shopping options, making it a hotspot for both thrill-seekers and casual explorers. Enjoy a day at the Charles Town Races and Slots, or immerse yourself in the local history while visiting the nearby national state park. With its blend of excitement and charm, Charles Town is perfect for couples and adventure enthusiasts looking to create lasting memories.

Best time to go to Hillsboro

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

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

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being open to adjusting your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is a fantastic tool that allows you to plan new adventures, pick up right where you left off, and easily manage your travel plans. You can find all the properties you've saved and booked organized into categories like Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Hillsboro getaway

Learn about the unique charm of Hillsboro with a stay in a private vacation home. There's no shortage of things to see and do in the area.With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Hillsboro

Are you searching for top things to see and do in the area? Venture out of your cozy vacation rental and experience everything that makes Hillsboro a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Doukenie Winery (1.1 mi / 1.8 km)
  • Breaux Vineyards (2.3 mi / 3.7 km)
  • 868 Estate Vineyards (2.5 mi / 4 km)
  • Stoneleigh Golf and Country Club (6 mi / 9.7 km)
  • Twin Oaks Tavern Winery (8.4 mi / 13.6 km)
  • Bluemont Vineyard (9.2 mi / 14.8 km)

Exploring the natural features in Hillsboro

Whether you're looking for adventure or just want to appreciate the scenery, Hillsboro is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Shenandoah Lake Beach (5 mi / 8 km)
  • Blue Ridge Center for Environmental Stewardship (6.6 mi / 10.6 km)
  • Oatlands Historic House and Gardens (12.2 mi / 19.6 km)
  • Evergreen Mills Equestrian and Hiking Trail (14 mi / 22.6 km)
  • Edgar Tillet Memorial Park (14.7 mi / 23.6 km)
  • Aldie Mill Historic Park (16 mi / 25.7 km)

Transportation to and around Hillsboro

The nearest airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 20.3 mi (32.7 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Washington Dulles Intl. Airport (IAD), which is 22.4 mi (36.1 km) away.

Frequently asked questions

What is the best area to stay in Hillsboro, Virginia, United States of America when booking a vacation rental?
When looking for a great area to stay in Hillsboro, Virginia, the charming neighborhood surrounding the historic downtown area is an excellent choice. This area is not only picturesque, with its quaint streets and beautiful landscapes, but it also offers easy access to some wonderful attractions. You can explore the nearby historic sites, such as the Hillsboro Old Stone Church, which dates back to the 19th century and is a lovely spot to appreciate the local heritage. Additionally, the surrounding countryside is superb for outdoor enthusiasts, featuring scenic trails and opportunities for hiking and biking.

In terms of vacation rentals, you'll find a variety of properties available, suiting different preferences and budgets.
How much does it cost to rent a vacation home in Hillsboro?
Prices for vacation rentals in Hillsboro 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 Hillsboro 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 Hillsboro vacation house rentals?
You can find great discounts on house rentals in Hillsboro 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.
Can I find long-stay vacation rentals in Hillsboro?
A long-stay vacation rental in Hillsboro 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 any Hillsboro vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hillsboro 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.
When is the best time to visit Hillsboro for a vacation rental?
The best time to visit Hillsboro for a vacation rental is during the peak season from July to September, particularly in August when the weather is at its warmest and most inviting. This vibrant period attracts travelers looking to immerse themselves in outdoor activities, such as hiking and exploring the picturesque vineyards that the region is renowned for.

During August, you can expect pleasant temperatures ranging from the mid-60s to the low 80s Fahrenheit, making it ideal for leisurely strolls through the charming town or enjoying a picnic in the scenic countryside. Hillsboro's close proximity to the beautiful Blue Ridge Mountains offers endless opportunities for adventure and sightseeing, ensuring that every moment spent here is filled with exploration and relaxation.

For those seeking a more budget-friendly option, consider visiting in November. This month, while quieter, showcases the stunning fall foliage and allows for peaceful exploration of the area's natural beauty, all while enjoying lower rates on vacation rentals.

Ultimately, your choice of when to visit Hillsboro depends on whether you prefer the lively option of summer adventures or the tranquil charm of fall's vibrant colors.
How early should I book a Hillsboro vacation rental?
Book your Hillsboro 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 Hillsboro, Virginia, United States of America?
In Hillsboro, Virginia, visitors can explore a charming small-town atmosphere with rich historical significance. The Hillsboro Historic District offers picturesque views and a glimpse into the past with its well-preserved 19th-century buildings. Nearby, the Hillsboro Heritage Museum provides insights into the area's history and culture.

For outdoor enthusiasts, the surrounding Loudoun Valley features beautiful scenic landscapes superb for hiking, biking, and enjoying nature. The nearby Potomac River offers opportunities for fishing and kayaking, making it a great spot for those who appreciate outdoor activities.

Wine lovers can take advantage of the numerous wineries in the surrounding Loudoun County, many of which are just a short drive away, providing scenic views and tastings of local wines. The area's rolling hills and vineyards create a picturesque backdrop for a relaxing day out.
Can I change or cancel my Hillsboro home rental booking on Vrbo?
To find Hillsboro 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 Hillsboro 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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