Chestnut Springs vacation rentals

We found 306 vacation rentals — enter your dates for availability

Select from 40 houses, 18 condos, and other vacation rentals to find the perfect place for your stay in Chestnut Springs. Vacation homes offer the amenities you expect for you and your friends, family, or even pets, such as a garden and pool. At the end of the day, you're sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Chestnut Springs

Showing deals for:May 29 - Jun 5

Image gallery for Spacious + Serene Mtn Top Escape, 4 En Suites

Main living floor contains dining, kitchen, living room, and half bath.
10 out of 10, Exceptional, (50 reviews)
Exceptional
(50 reviews)

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort

8% off
Price is $325
$2,274 for 7 nights
All fees included
Spacious + Serene Mtn Top Escape, 4 En Suites

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Find out more about Chestnut Springs

Why visit Chestnut Springs

  • Adventure Activities: Chestnut Springs is a haven for ski and outdoor enthusiasts, offering thrilling winter sports and adventures.
  • Scenic Natural Beauty: Enjoy stunning winter views and picturesque landscapes ideal for relaxation and recreation.
  • Attractions for Everyone: Explore nearby dog parks, visitor centers, and historic homes, catering to diverse interests.
  • Comfortable Accommodations: Choose from cozy cabins, private homes, and condos, perfect for families or solo travelers.
  • Community Vibe: Experience the vibrant local atmosphere and immerse yourself in the charm of Roseland.

Popular types of accommodation around Chestnut Springs

If you're planning a getaway to Chestnut Springs, you're in for a treat. Our most popular vacation rental options include houses, cozy condos, and charming cabins. Whether you're looking to relax by the outdoor pool, take a dip in a swimming pool, or stay active at the fitness center, you'll find the perfect spot to unwind and enjoy your stay in this beautiful destination.

  • Houses: These spacious homes are the top choice for visitors, offering a perfect blend of comfort and privacy for families and groups.
  • Condos: A popular option for travelers seeking convenience, these modern accommodations often come with shared amenities like pools and fitness centers.
  • Cabins: Ideal for those looking to immerse themselves in nature, these rustic retreats provide a cozy atmosphere.
  • Apartments: A great choice for solo travelers or couples, these rentals offer the comforts of home in a compact space.
  • Cottages: These charming dwellings provide a quaint and intimate setting, perfect for a romantic getaway.**

Top attractions near Chestnut Springs

Chestnut Springs in Roseland, Virginia, is perfect for ski and adventure enthusiasts seeking an active vacation. Visitors can explore popular attractions like ski resorts, visitor centers, and historic houses, making it an ideal destination for outdoor adventures and cultural experiences. Whether you're traveling solo or with family and friends, Chestnut Springs offers a variety of activities to ensure a memorable getaway.

  • Wintergreen Resort: A premier ski resort offering thrilling winter sports, cozy lodges, and stunning mountain views. Experience outdoor adventures year-round, including hiking and mountain biking during warmer months.
  • Raven's Roost Overlook: An enchanting lookout point perfect for romantic getaways and outdoor enthusiasts. Enjoy breathtaking vistas of the Blue Ridge Mountains, especially at sunset.
  • Blue Ridge Parkway North Entrance: A gateway to scenic drives, this visitor center offers family-friendly activities and access to hiking trails with panoramic views of nature's beauty.

Things to do recommended for couples

Experience romance in Chestnut Springs. Hit the slopes at Wintergreen Resort, savor fine wines at Afton Mountain Vineyards, and unwind with a couples massage at All's Well Massage Studio. Enjoy adventure, entertainment, and relaxation all in one enchanting getaway.

Things to do recommended for families

Your family will love exploring the Sherando Lake Recreation Area, just 4 miles from Chestnut Springs. Enjoy wellness and relaxation while swimming, hiking, or picnicking in the beautiful natural surroundings—perfect for making lasting memories together.

Things to do recommended for groups

Groups visiting Chestnut Springs can indulge in tastings at Bold Rock Hard Cider, enjoy a round at Stoney Creek Golf Course, and embark on an adventure along the scenic Reids Gap Trailhead. Each offers unique vibes for an unforgettable group experience.

*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 around Chestnut Springs

If you're traveling with a group, with family, bringing pets, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chestnut Springs with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Chestnut Springs with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chestnut Springs: For many families, a trip isn't truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chestnut Springs: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chestnut Springs

Chestnut Springs, nestled in Roseland, Virginia, offers an unforgettable vacation experience for adventure seekers and families alike. With its stunning winter views and scenic surroundings, visitors can enjoy skiing and outdoor excursions. Nearby attractions include a relaxing dog park and picturesque water views, making it a perfect destination for both relaxation and recreation. Explore the vibrant atmosphere of the local school district and immerse yourself in the natural beauty that Chestnut Springs and its surroundings have to offer.

  • Waynesboro: Located a mere 10 miles from Chestnut Springs, Waynesboro is a vibrant city known for its stunning outdoor scenery and adventurous spirit. Surrounded by the natural beauty of the Shenandoah Valley, visitors can explore numerous recreational areas that include hiking trails and picturesque lakes. The city is also a gateway to the nearby national parks, perfect for those looking to immerse themselves in nature. Whether you're skiing in the winter or enjoying a leisurely day by the lake, Waynesboro offers a variety of activities that cater to adventure seekers and nature lovers alike.
  • Wintergreen: Situated just 4 miles from Chestnut Springs, Wintergreen is a charming village renowned for its exceptional skiing and outdoor sports. This picturesque destination boasts a ski resort that attracts winter sports enthusiasts from near and far. Visitors can enjoy the thrill of skiing and snowboarding on well-maintained slopes, as well as other activities such as snowshoeing and hiking during warmer months. With its breathtaking views of the Blue Ridge Mountains and proximity to national parks, Wintergreen is a perfect spot for those looking to combine adventure with stunning natural landscapes.
  • Nellysford: Nestled in the heart of Nellysford, which encompasses Chestnut Springs, this city offers a delightful blend of adventure and natural wonders. Known for its ski resorts and outdoor sports, Nellysford is a haven for those seeking thrilling experiences year-round. With the nearby national and state parks, visitors can explore lush trails, pristine lakes, and diverse wildlife. Whether you're hitting the slopes in winter or enjoying the vibrant scenery in summer, Nellysford promises an exciting and memorable getaway for adventurers and nature enthusiasts alike.

Best time to go to Chestnut Springs

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.4°F (0.8°C)Light RainMostly SunnyAverageSlightly High
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly High
March44.6°F (7.0°C)Light RainMostly SunnySlightly LowSlightly Low
April54.9°F (12.7°C)Light RainMostly SunnySlightly LowSlightly Low
May64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
June72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
July76.6°F (24.8°C)Light RainMostly SunnySlightly HighSlightly Low
August74.3°F (23.5°C)Light RainMostly SunnySlightly HighAverage
September68.0°F (20.0°C)Light RainMostly SunnySlightly LowAverage
October56.8°F (13.8°C)Light RainMostly SunnySlightly HighAverage
November44.8°F (7.1°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Try being flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you can quickly access member discounts and earn and redeem OneKeyCash on eligible reservations. Sign up today and start enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is designed to help you plan your travels with ease. You can create new trips, continue working on your plans, or review and organize your existing bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Chestnut Springs?
In Chestnut Springs, vacation houses are the most popular type of rental, with about 36 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or larger groups. Many vacation houses also include outdoor spaces, such as decks or patios, for enjoying the beautiful Virginia scenery. Additionally, there are around 18 condos, which offer a more compact and convenient option, often located closer to local attractions. For those seeking a rustic experience, about 10 cabins can be found, providing a cozy atmosphere surrounded by nature.
How much does it cost to rent a vacation home in Chestnut Springs?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Chestnut Springs?
In Chestnut Springs, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals conveniently. Many rentals also feature cozy fireplaces, great for warming up after a day of exploring the scenic surroundings. Outdoor spaces like decks or patios provide a lovely setting for guests to relax and enjoy the fresh air. Onsite parking is another common amenity, making it easy for travelers to access their accommodations. Additionally, many properties include coffee and tea makers, ensuring that guests can enjoy a warm beverage at any time.
Can I find family house rentals in Chestnut Springs?
In Chestnut Springs, Virginia, families can find a variety of vacation rentals—there are 51 options available throughout the area. This charming locale is surrounded by natural beauty, making it an excellent choice for group getaways. Many properties offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces superb for relaxation or play. Amenities such as Wi-Fi and air conditioning are typically included for added comfort.

Visitors can enjoy nearby attractions such as scenic hiking trails and picturesque parks, providing opportunities for family-friendly activities and exploration.
Can I rent a vacation home with a pool or hot tub in Chestnut Springs?
In Chestnut Springs, Virginia, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 54 properties offering pools and 25 providing hot tubs. This picturesque area is known for its natural beauty and outdoor activities, making it an excellent choice for travelers seeking relaxation and recreation.

Rentals here typically boast amenities such as private pools, inviting hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens, superb for families or groups looking to unwind after a day of exploring. Many properties may also include cozy living spaces, fire pits, and access to beautiful hiking trails, allowing guests to immerse themselves in the scenic surroundings while enjoying the comforts of home.
Are there any Chestnut Springs vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chestnut Springs 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.
Can I book pet-friendly vacation rentals in Chestnut Springs?
Yes, you can book pet-friendly vacation rentals in Chestnut Springs, Virginia, where there are around 30 options available. This area is known for its beautiful natural scenery and outdoor recreational opportunities, making it a great choice for travelers with pets. Many of the rentals come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or yards that are great for pets to enjoy.

Chestnut Springs is located near the scenic George Washington National Forest, providing ample opportunities for hiking and exploring the great outdoors with your furry friends. Additionally, the region offers charming local shops and eateries that welcome pets, enhancing your stay in this picturesque setting.
Can I find long-stay vacation rentals in Chestnut Springs?
A long-stay vacation rental in Chestnut Springs 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.
When is the best time to visit Chestnut Springs for a vacation rental?
The best time to visit Chestnut Springs for a vacation rental is during the peak season from December to February, with January being particularly popular. This winter wonderland attracts travelers eager to embrace the charm of the season, offering a variety of outdoor activities like skiing, snowboarding, and cozy fireside relaxation. The picturesque landscape transforms into a snowy retreat, great for those who appreciate the beauty of winter.

During January, temperatures typically range from the low 20s to mid-40s Fahrenheit, providing a crisp, refreshing atmosphere for outdoor exploration. Visitors can take advantage of the scenic trails for snowshoeing or enjoy the serene surroundings while sipping hot cocoa in one of the area's inviting cabins.

If you're looking for more budget-friendly options, consider planning your trip in May. This month offers a unique opportunity to experience the lush greenery of spring without the bustling crowds. It's an ideal time for leisurely hikes and enjoying the blooming wildflowers, making it a beautiful backdrop for outdoor activities.

Ultimately, your ideal visit to Chestnut Springs will depend on whether you prefer the vibrant winter atmosphere full of holiday cheer and adventure or the tranquil beauty of spring.
Are there any remote work vacation rentals in Chestnut Springs?
In Chestnut Springs, Virginia, there are numerous remote work-friendly vacation rentals available, with around 68 options to choose from. Travelers can expect accommodations equipped with essential amenities to support productivity, including high-speed internet and Wi-Fi access within the units. Many rentals also feature dedicated workspaces with desks and chairs, ensuring a comfortable environment for remote work.

The area offers a tranquil setting, ideal for those looking to balance work and relaxation. Vacation rentals often include cozy living areas and fully equipped kitchens, allowing for a home-like experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Chestnut Springs vacation rental?
Book your Chestnut Springs 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 Chestnut Springs, Virginia, United States of America?
In Chestnut Springs, Virginia, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The nearby Blue Ridge Parkway offers breathtaking views and numerous hiking trails, making it a popular destination for nature enthusiasts. Additionally, the charming town of Nelson County is known for its wineries and breweries, providing opportunities for tastings and tours in a picturesque setting.

For those interested in history, the historic sites in nearby Charlottesville, including Monticello, the home of Thomas Jefferson, and the University of Virginia, provide rich cultural experiences. Travelers can also explore the scenic hiking paths and waterfalls in the nearby Shenandoah National Park, superb for a day trip filled with outdoor adventure.
Can I change or cancel my Chestnut Springs home rental booking on Vrbo?
To find Chestnut Springs 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 Chestnut Springs 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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