Chestnut Springs holiday lettings

We found 279 holiday rentals — enter your dates for availability

Select from 39 houses, 17 flats and other holiday rentals to find the perfect place for your stay in Chestnut Springs. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Chestnut Springs

Showing deals for:14 Nov - 21 Nov

Image gallery for Wintergreen Resort: Weeping Rock Retreat

Exterior
10 out of 10 rating
Exceptional
(5 reviews)

Wintergreen Resort: Weeping Rock Retreat

Nellysford, VA

14% off
Price is £1,277
£182 per night
includes taxes & fees
Wintergreen Resort: Weeping Rock Retreat

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

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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

Frequently asked questions

What is the most popular type of holiday rental in Chestnut Springs?
In Chestnut Springs, holiday houses are the most popular rental option, with about 38 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them superb for families or larger groups looking to enjoy the picturesque Virginia countryside. Additionally, there are around 16 condos, which offer a more compact stay with amenities such as communal pools and fitness centres, ideal for those who prefer a low-maintenance option. There are also several cabins, cottages, and chalets scattered around, providing a charming rustic experience that immerses guests in nature.
How much does it cost to rent a holiday home in Chestnut Springs?
Prices for holiday rentals in Chestnut Springs 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 Chestnut Springs 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 Chestnut Springs holiday house rentals?
You can find great discounts on house rentals in Chestnut Springs 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.
Are there any Chestnut Springs holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chestnut Springs 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.
Can I find long-stay holiday rentals in Chestnut Springs?
A long-stay holiday rental in Chestnut Springs 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.
When is the best time to visit Chestnut Springs for a holiday rental?
September is the most popular time to visit Chestnut Springs, offering a delightful blend of autumn colours and mild weather. This period falls within the peak season, which spans from July to September, attracting those eager to experience the stunning natural beauty and outdoor activities of the Virginia mountains. With temperatures generally hovering in the mid-teens Celsius, the climate is great for hiking, biking, and sightseeing in the picturesque surroundings.

During September, the vibrant foliage begins to emerge, making it an ideal time for leisurely walks along the scenic trails or visits to local attractions. The area's charm is accentuated by the cooler evenings, great for enjoying a cosy night by a fire after a day of exploration.

If you're looking for a more budget-conscious option, consider visiting in December. While this month is typically quieter, it offers unique winter activities and a peaceful atmosphere, allowing you to enjoy the beauty of Chestnut Springs without the crowds.
Are there any remote work holiday rentals in Chestnut Springs?
In Chestnut Springs, Virginia, there are numerous remote work-friendly holiday rentals available, with around 64 options to choose from. Travellers can expect properties equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces with desks and chairs, and additional features like safe storage and computer monitors to facilitate a productive work environment. Many of these rentals also offer comfortable living areas and kitchens, making them suitable for extended stays. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Chestnut Springs holiday rental?
Book your Chestnut Springs 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.
Can I change or cancel my Chestnut Springs home rental booking on Vrbo?
To find Chestnut Springs 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 Chestnut Springs 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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