Chestnut Springs vacation rentals

We found 280 vacation rentals — enter your dates for availability

Select from 39 houses, 17 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:Nov 7 - Nov 14
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Find out more about Chestnut Springs

Find out more about Chestnut Springs

Why visit Chestnut Springs

  1. Outdoor Adventures: Chestnut Springs is perfect for skiing and various outdoor sports, making it an ideal destination for adventure seekers.
  2. Stunning Natural Attractions: Explore national parks, beautiful waterfalls, and fishing lakes that showcase the area's scenic beauty.
  3. Family-Friendly Activities: Enjoy local attractions like Fairy Springs Park and a water park, perfect for families looking for fun.
  4. Welcoming Community: Experience the vibrant atmosphere filled with friendly locals, enhancing your vacation experience.
  5. Diverse Accommodation Options: Choose from cozy cabins, condos, or private homes to find the perfect place for your stay.

Popular types of accommodation around Chestnut Springs

Chestnut Springs offers a fantastic selection of vacation rentals, including private homes, condos, and cozy cabins. Whether you're seeking a place with an outdoor pool to relax or convenient parking, you'll find the perfect fit for your getaway. With an emphasis on transparency and savings, our platform helps you discover the ideal accommodation for your trip to Chestnut Springs, ensuring a memorable stay for you and your family.

  • Houses: The top choice for visitors to Chestnut Springs, offering ample space and amenities for families and groups.
  • Condos: A popular option for those seeking modern conveniences and shared facilities in a vibrant community setting.
  • Cabins: Ideal for nature enthusiasts, these cozy retreats provide a rustic atmosphere surrounded by beautiful landscapes.
  • Apartments: A practical choice for travelers looking for comfort and accessibility in a home-like environment.
  • Cottages: These quaint accommodations offer a charming and intimate experience, perfect for a romantic getaway.**

Top attractions near Chestnut Springs

Chestnut Springs in Roseland, Virginia, is perfect for skiing, adventure, and sports vacations. Visitors can explore various attractions, including visitor centers, national state parks, and stunning waterfalls. The area offers a wealth of outdoor and cultural experiences, ideal for families and adventure seekers alike. Don't miss out on the local water park, swim meets, and the family-friendly Fairy Springs Park for a fun-filled trip.

  1. Blue Ridge Parkway North Entrance: This visitor center is 8 miles from Chestnut Springs, offering a perfect blend of adventure and family-friendly activities. Explore the stunning landscapes, enjoy educational exhibits, and gather information for your journey along the scenic Blue Ridge Parkway.
  2. Raven's Roost Overlook: Located only 0.7 miles away, this lookout provides breathtaking views, making it an ideal spot for romance and adventure. Capture unforgettable moments while surrounded by the beauty of nature.
  3. Rockfish Gap Entrance Shenandoah: Situated 9 miles from Chestnut Springs, this national park entrance invites you to experience thrilling outdoor adventures and stunning scenery, perfect for hikers and nature lovers alike.

Things to do recommended for couples

For a romantic getaway in Chestnut Springs, enjoy skiing at Wintergreen Resort, just 1 mile away. Savor fine wines at Veritas Vineyard, 8 miles from your stay, and unwind with a couples massage at All's Well Massage Studio, located 17 miles away. Perfect for lovebirds!

Things to do recommended for families

Families visiting Chestnut Springs can enjoy a day at Sherando Lake Recreation Area, located 4 miles away. This beautiful spot offers wellness and relaxation, perfect for a family picnic and outdoor activities, making it a great destination for kids and parents alike.

What do I need to keep in mind when booking a vacation around Chestnut Springs

When you're planning a trip—whether it's with a group, family, pets, or for an extended stay—be sure to use the right filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chestnut Springs with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Chestnut Springs with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Chestnut Springs: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, 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 Chestnut Springs: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rental options. Don't forget to include features like parking, 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 a perfect blend of adventure and relaxation. Ideal for skiing and sports enthusiasts, this charming neighborhood features scenic views and family-friendly activities. Nearby, you can enjoy the refreshing waters of fishing lakes, and explore the vibrant atmosphere filled with friendly locals. Whether you're seeking summer thrills or peaceful excursions, Chestnut Springs is the perfect destination for an unforgettable vacation experience.

  • Waynesboro: Located 10 miles from Chestnut Springs, Waynesboro is a vibrant city known for its stunning outdoor scenery and adventurous spirit. This destination attracts nature lovers and thrill-seekers alike, offering a variety of recreational activities. Visitors can explore the nearby national parks, take in breathtaking views at the local lakes, or hit the slopes at nearby ski fields. The combination of outdoor adventures and picturesque landscapes makes Waynesboro an ideal stop for those looking to immerse themselves in Virginia's natural beauty.
  • Wintergreen: Just 4 miles away from Chestnut Springs, Wintergreen is a charming village that provides an exhilarating escape for ski and adventure enthusiasts. With its well-known ski resort and accessible ski fields, Wintergreen is a winter wonderland for those who love snow sports. In addition to skiing, visitors can enjoy the surrounding national parks and picturesque lakes that enhance the area's scenic appeal. Whether you’re shredding the slopes or hiking through the lush landscapes, Wintergreen promises an unforgettable experience.
  • Afton: Afton, located 9 miles from Chestnut Springs, is a city that offers a perfect blend of outdoor adventure and breathtaking scenery. This destination is particularly popular among skiing aficionados, with numerous ski resorts and fields nearby. Afton is also home to beautiful national parks and lakes, providing ample opportunities for hiking, fishing, and exploring the great outdoors. Whether you're hitting the slopes in winter or enjoying the stunning landscapes in warmer months, Afton is a must-visit for any adventure seeker.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you eager to save on your upcoming trip? Keeping your travel dates flexible can often lead to significant savings, as prices can vary. Additionally, if you opt for a longer stay, you may unlock even greater discounts. 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. We're here to help you find the best options for your needs!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you’ll gain immediate access to member savings and the opportunity to 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 create new travel plans, manage your ongoing arrangements, and organize your bookings with ease. Your saved and booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chestnut Springs?
According to our research, condos are the most sought-after property type in Chestnut Springs. But having said that, everyone's idea of the perfect trip can vary. Vrbo has vacation rentals of all sizes and shapes, so you're sure to discover the perfect match.
How much does it cost to rent a vacation rental in Chestnut Springs?
Property type, season and length of stay are some of the conditions that can influence the price of a vacation home. Simply click on your travel dates to find your perfect escape. From quaint country cottages to plush villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Chestnut Springs?
The average price for a vacation home by the beach in Chestnut Springs depends on when you're traveling and the type and size of property you're searching for. You can easily find prices on Vrbo by entering your travel dates and destination. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Chestnut Springs?
With 56 properties that welcome pets, your furry friend can also come along on your Chestnut Springs getaway. Use the filter tool to browse our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Chestnut Springs?
Add another level of fun to your adventure by booking your crew into one of the 37 houses with a private pool in Chestnut Springs. Use our search filter to find properties with pools on Vrbo, then spend leisurely days frolicking in a swimming pool that's for your exclusive use.
What are popular rental amenities in Chestnut Springs?
A swimming pool, tennis and ski-in/ski-out facilities are the most popular rental amenities in Chestnut Springs. Whether you're planning to travel alone, with your spouse or a bunch of friends, Vrbo can help you find a vacation home that suits your style with a load of extras you'll love.
Are there large group vacation rentals in Chestnut Springs?
You'll discover 30 properties in Chestnut Springs that can accommodate a group of 10 or more guests. Whether you're organizing time away with the family or an event like an anniversary, there's enough space to get your loved ones together under the same roof.
Are there vacation rentals in Chestnut Springs that welcome kids?
With 56 family-friendly vacation properties to choose from in Chestnut Springs, now is the perfect time to introduce the kids to the thrills of travel. Check our "Properties good for families" filter box to view stays loaded with amenities ideal for families on the move, like full kitchens, yards, entertainment areas and hot tubs.
Can I find two-bedroom vacation rentals in Chestnut Springs?
Gather your besties and experience complete comfort and privacy in one of the eight two-bedroom vacation homes Chestnut Springs has to offer.
Are there vacation rentals with WiFi in Chestnut Springs?
Chestnut Springs has 26 vacation rentals with WiFi, so you can stay connected while you're traveling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to scrolling social media, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Chestnut Springs?
Work out your travel dates and then make use of the filters to locate vacation rentals with air conditioning in Chestnut Springs on Vrbo. With 52 air-conditioned properties to choose from here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Chestnut Springs?
The minimum required age is normally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your chosen Chestnut Springs vacation rental before booking your stay.
How long can I rent a vacation rental in Chestnut Springs for?
The amount of time you can book a Chestnut Springs vacation rental for varies depending on the property. Just put in your preferred travel dates to find options that offer long-term stays. They have everything you need to make your extended trip more enjoyable such as air conditioning and laundries. Some Vrbo vacation homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Chestnut Springs?
On Vrbo, we've got some fantastic deals and discounts for Chestnut Springs. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a mini getaway or an extended escape, Vrbo has a variety of options for all budgets and styles.