Ashland holiday lettings

We found 68 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Ashland that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a garden and pool. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Head to the theatrical city of Ashland

The area's theatre scene and live music are just some of the reasons to come on holiday to Ashland. Renowned for its football matches, gardens and university setting, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Ashland

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Ashland a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kings Dominion (5.8 mi / 9.3 km)
  • Richmond Raceway (11.6 mi / 18.7 km)
  • Country Club of Virginia (13.3 mi / 21.4 km)
  • Mattaponi Springs Golf Club (14.7 mi / 23.7 km)
  • Libby Hill Park (16.3 mi / 26.3 km)
  • James River Cellars Winery (3.9 mi / 6.3 km)

Exploring the natural landscape of Ashland

Whether you're an active traveller or just want to spend some time taking in the scenery, Ashland is a great spot to appreciate mother nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lewis Ginter Botanical Garden (9.5 mi / 15.3 km)
  • Maymont Park (15.4 mi / 24.8 km)
  • James River (15.8 mi / 25.4 km)
  • Libby Hill Park (16.3 mi / 26.3 km)
  • Virginia Capital Trail: Richmond Trailhead (16.4 mi / 26.4 km)
  • Dorey Park (21.5 mi / 34.7 km)

Transport options to and around Ashland

Fly into Richmond, VA (RIC-Richmond Intl.), the closest airport, located 19.1 mi (30.7 km) from the city centre.

If you'd rather travel by train, the main station serving the city is Ashland Station.

Frequently asked questions

What is the best area to stay in Ashland when booking a holiday rental?
When considering a holiday rental in Ashland, Virginia, the downtown area emerges as an excellent choice. This charming neighbourhood boasts a delightful blend of historic architecture and modern amenities, providing a vibrant atmosphere for visitors. One of the top attractions in this area is the Ashland Theatre, a beautifully restored venue that hosts a variety of performances and events, making it a cultural hub for the community. Additionally, the nearby Randolph-Macon College adds to the lively vibe, often hosting events and offering picturesque campus walks.

Another appealing neighbourhood is the area surrounding the Ashland Museum. Staying here allows easy access to this local gem, where you can delve into the rich history of the town and learn about its significance in Virginia's development. The proximity to various shops, cafes, and restaurants enhances the experience, ensuring you have everything you need within walking distance.
How much does it cost to rent a holiday home in Ashland?
Prices for holiday rentals in Ashland 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 Ashland 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 Ashland holiday house rentals?
You can find great discounts on house rentals in Ashland 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.
What is the most popular type of holiday rental accomodation in Ashland?
In Ashland, holiday houses are the most popular type of rental accommodation, with several available throughout the town. These homes generally feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many properties also include outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring the local attractions.
Are there any family house rentals in Ashland?
In Ashland, Virginia, there are several family-friendly holiday rentals available, making it an excellent choice for those travelling with children. The town offers a quaint atmosphere, with properties situated close to local parks and recreational areas. Many of these homes provide spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy playtime.
Can I find long-stay holiday rentals in Ashland?
A long-stay holiday rental in Ashland 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Ashland?
In Ashland, Virginia, there are several remote work holiday rentals available, making it an excellent choice for those looking to combine work and leisure. These properties typically feature dedicated workspaces, including desks and comfortable chairs, as well as reliable Wi-Fi to ensure a productive environment. Many rentals also come with amenities that enhance the work-from-home experience, such as office supplies and quiet surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Ashland 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 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 Ashland?
In Ashland, popular rental amenities include kitchens, which allow guests to prepare their own meals, along with free Wi-Fi for staying connected. Many rentals also feature coffee makers, cookware, dishware, and utensils, making it convenient for travellers to enjoy home-cooked meals. Additionally, dishwashers are commonly found in these properties, providing a straightforward way to clean up after enjoying a meal.
When is the best time to visit Ashland for a holiday rental?
The best time to book a holiday rental in Ashland is during the peak season from June to August. This period is particularly popular among travellers who seek vibrant cultural experiences, as it coincides with the renowned Oregon Shakespeare Festival. Visitors can engage in world-class performances while enjoying the warm summer weather, great for outdoor activities and exploring the charming downtown area.

July stands out as the most popular month for holiday rentals in Ashland, with a lively atmosphere that attracts theatre enthusiasts and families alike. During this time, expect comfortable temperatures, often reaching the low 30s Celsius, making it ideal for alfresco dining and leisurely strolls through Lithia Park, where you can enjoy beautiful gardens and serene landscapes.

For those on a budget, consider visiting in November. This month offers a unique opportunity to experience Ashland's quieter charm, with fewer crowds and the chance to witness the beauty of autumn foliage. It's a great time for cosy evenings in your rental after exploring local shops and cafes.
How early should I book a Ashland holiday rental?
Book your Ashland holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ashland?
In Ashland, Virginia, visitors can explore a variety of attractions that showcase the town's rich history and charming atmosphere. The historic downtown area features a mix of quaint shops, local eateries, and vibrant arts scenes, making it a delightful place to stroll and discover. One key attraction is the Ashland Museum, which offers insights into the town's past and its significance in the Civil War.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland holiday 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 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 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, Vrbo 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 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 Ashland holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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