Castleton holiday lettings

We found 106 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Castleton that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, such as parking and air conditioning. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Castleton

Showing deals for:14 Nov - 21 Nov

Image gallery for Serenity and adventure at historic Blue Ridge Farm

Farmhouse in summer
10 out of 10 rating
Exceptional
(112 reviews)

Serenity and adventure at historic Blue Ridge Farm

Sperryville, VA

8% off
Price is £2,881
£412 per night
includes taxes & fees
Serenity and adventure at historic Blue Ridge Farm

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Castleton

Find out more about Castleton

Book a holiday rental for your Castleton getaway

Learn about the unique charm of Castleton with a stay in a holiday home rental. This city has something for everyone. 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 Castleton

Do you want to discover top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Castleton a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Little Washington Winery (7.1 mi / 11.4 km)
  • Old House Vineyards (15.2 mi / 24.4 km)
  • Yogi Bear's Jellystone Park (16.1 mi / 25.9 km)
  • Linden Vineyards (19.1 mi / 30.7 km)
  • Gray Ghost Winery (7.5 mi / 12 km)
  • Sharp Rock Vineyards (8.8 mi / 14.1 km)

Exploring the natural landscape of Castleton

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Castleton is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Old Rag Mountain (11.9 mi / 19.2 km)
  • Thorton Gap Entrance Shenandoah (12.2 mi / 19.6 km)
  • Mary's Rock Summit Trailhead (12.2 mi / 19.6 km)
  • Stony Man (14.4 mi / 23.2 km)
  • Rose River Falls (17.1 mi / 27.5 km)
  • Dark Hollow Falls (18.1 mi / 29.2 km)

Transport to and around Castleton

The nearest airport is in Manassas, VA (MNZ-Manassas Regional), located 33.1 mi (53.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Castleton when booking a holiday rental?
When considering a holiday rental in Castleton, Virginia, a popular area to stay is near the charming countryside surrounding the quaint village centre. This location offers a serene atmosphere with stunning views of the Blue Ridge Mountains, making it ideal for those looking to escape the hustle and bustle of city life. The village itself is small but inviting, with a handful of properties available that capture the rustic charm of the region.

Staying in this area provides convenient access to the breathtaking Shenandoah National Park, which is a mere stone's throw away and offers numerous hiking trails, scenic drives, and opportunities for wildlife viewing. For those interested in local history, the nearby Castleton Farms is worth a visit, renowned for its picturesque landscapes and equestrian events.
How much does it cost to rent a holiday home in Castleton?
Prices for holiday rentals in Castleton 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 Castleton 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 Castleton holiday house rentals?
You can find great discounts on house rentals in Castleton 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 Castleton?
In Castleton, holiday houses and cottages are the most popular types of rental accommodations, with several options available in the area. These properties are typically found in tranquil settings, offering a peaceful retreat for visitors looking to explore the scenic beauty of Virginia's countryside. Most holiday houses feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Cottages, on the other hand, often provide a charming, rustic atmosphere with cosy interiors and sometimes even outdoor spaces for relaxation.
Are there any family house rentals in Castleton?
In Castleton, Virginia, there are some family-friendly house rentals available, with around ten options to choose from. This charming area is known for its scenic beauty and outdoor activities, making it ideal for families seeking adventure and relaxation. Many of these homes provide spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces for children to play and explore.
Can I rent a holiday home with a pool or hot tub in Castleton?
In Castleton, Virginia, there are several holiday homes available for rent that feature pools or hot tubs. This charming rural area offers a peaceful retreat surrounded by the beautiful landscapes of the Blue Ridge Mountains. Many of the properties come with amenities such as private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens, making them ideal for family gatherings or group getaways.
Can I find long-stay holiday rentals in Castleton?
A long-stay holiday rental in Castleton 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 pet-friendly house rentals in Castleton?
In Castleton, Virginia, there are several pet-friendly house rentals available for travellers seeking a welcoming environment for their furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ensuring a pleasant stay for both pets and their owners.
Are there any remote work holiday rentals in Castleton?
In Castleton, Virginia, travellers seeking remote work-friendly holiday rentals will find around 10 options available. This picturesque area offers a tranquil setting, ideal for those looking to balance work and leisure. Many of these properties come equipped with essential amenities such as Wi-Fi, desks, and comfortable desk chairs, ensuring a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Castleton holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Castleton 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 Castleton?
In Castleton, popular rental amenities often include stunning mountain views and fully equipped kitchens, making it easy for guests to prepare meals while enjoying the scenic backdrop. Many properties are situated near opportunities for antiquing, allowing travellers to explore local shops and find unique treasures. Additionally, some rentals permit events, providing flexibility for gatherings or celebrations. Fitness facilities are also nearby, suiting those looking to maintain their exercise routines during their stay.
When is the best time to visit Castleton for a holiday rental?
July is the most popular time to visit Castleton, Virginia, making it an ideal month for travellers seeking a vibrant holiday experience. This period falls within the peak season from June to August, when the warm temperatures and lush landscapes invite visitors to partake in a variety of outdoor activities. With average highs around 30°C, July provides a great backdrop for hiking in the nearby Appalachian Mountains or enjoying leisurely afternoons at local wineries.

During this peak season, you can expect a lively atmosphere with plenty of fellow adventurers exploring the area. Whether you're hiking the trails or simply soaking in the picturesque views, Castleton offers numerous opportunities to connect with nature and indulge in local culture.

For those looking to save a bit while still enjoying the charm of Castleton, consider planning your visit in November. This month brings a quieter vibe, allowing you to appreciate the beautiful autumn scenery and experience the local community at a more relaxed pace. The crisp air and stunning fall foliage create a serene setting for exploration.
How early should I book a Castleton holiday rental?
Book your Castleton 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 Castleton?
In Castleton, Virginia, visitors can enjoy a range of attractions that highlight the area's natural beauty and historical significance. The nearby Shenandoah National Park offers breathtaking hiking trails, scenic overlooks, and opportunities for wildlife viewing, making it a popular destination for outdoor enthusiasts. Within Castleton itself, the historic Castleton Farms provides a picturesque setting, often hosting events and showcasing the region's charm. The local landscape is dotted with vineyards and wineries, such as those found on the nearby Monticello Wine Trail, where guests can indulge in tastings and tours.
Can I change or cancel my Castleton home rental booking on Vrbo?
To find Castleton 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Castleton 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.

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