Discover Your Perfect Wintergreen Resort Vacation Homes

Best Vacation Homes in Wintergreen Resort

Why Choose Rent By Owner for your Wintergreen Resort Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Wintergreen Resort Vacation Rentals

Where are the best neighborhoods to stay in Wintergreen Resort?

When planning your getaway to Wintergreen Resort in Nellysford, Virginia, choosing the right neighborhood can enhance your entire experience. Whether you prefer the scenic tranquility of the surrounding mountains or the convenience of nearby amenities, each area offers a unique atmosphere suited to different travel styles. Exploring options within Nellysford and its neighboring communities allows you to find the perfect setting for your stay, ensuring a memorable and comfortable vacation. Trust that the local properties provide reliable and quality accommodation choices, making your booking process smooth and stress-free.

Treeloft

Situated within the scenic area surrounding Wintergreen Resort, Treeloft offers a peaceful retreat with easy access to the region's outdoor activities. Staying here provides a convenient base for exploring the natural beauty and recreational opportunities nearby.

View 1034+ Rentals in Treeloft

Pedlars Edge

Located close to the thriving heart of Nellysford, Pedlars Edge combines comfort with proximity to local amenities, making it an ideal choice for travelers seeking both relaxation and convenience in this part of Virginia.

View 1040+ Rentals in Pedlars Edge

Deer Springs

Deer Springs offers a tranquil setting nestled near the mountains and wooded landscapes that define this destination, providing a serene escape just moments from the area's popular outdoor pursuits.

View 993+ Rentals in Deer Springs

Chestnut Springs

This neighborhood is perfect for those who want to enjoy the scenic views and peaceful atmosphere of the region while remaining close to Wintergreen’s outdoor adventures and local attractions.

View 81+ Rentals in Chestnut Springs

Laurel Ridge

Perched amidst lush surroundings, Laurel Ridge offers a charming stay with easy access to hiking trails and the natural wonders of the area, ideal for outdoor enthusiasts visiting the region.

View 1022+ Rentals in Laurel Ridge

Best Times to Visit Wintergreen Resort

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience all the natural beauty and outdoor activities this destination has to offer, making your stay in the region even more memorable and enjoyable.

Peak Season Highlights

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Winter (December to February)

During the winter months, you can enjoy the region's winter sports and scenic snowy landscapes, making it an ideal time for cozy stays in the area’s vacation rentals.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 25°F
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Summer (June to August)

The summer season offers warm weather perfect for outdoor activities and exploring the beautiful scenery, attracting visitors seeking a lively getaway in the region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F

Off-Season Highlights

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Spring (March to May)

Spring brings milder temperatures and blooming landscapes, making it a peaceful time to experience the area's natural beauty without the summer crowds.

Average Temperature Daytime: 55°F to 70°F - Nighttime: 40°F to 50°F
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Fall (September to November)

Autumn showcases vibrant foliage and cooler temperatures, offering a tranquil atmosphere for those looking to enjoy the region's scenic views in a relaxed setting.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Wintergreen Resort

How to Book Your Wintergreen Resort Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Wintergreen Resort

More Top-Rated Vacation Rentals in Wintergreen Resort Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to scenic outdoor pools or hot tubs for relaxation after your outdoor activities.
  • Take advantage of spacious decks or patios perfect for outdoor dining and unwinding in the fresh air.
  • Benefit from well-maintained walking trails or hiking paths that showcase the natural beauty of the area.
  • Make use of outdoor fire pits or fireplaces ideal for cozy evenings under the stars.
  • Utilize established picnic areas equipped with tables and grills for outdoor gatherings.
  • Experience the thrill of nearby golf courses designed for all skill levels, blending recreation with the scenic landscape.
  • Access to outdoor sports facilities such as tennis courts or volleyball courts, for active pursuits amidst nature.

Top Attractions Around Wintergreen Resort

What attractions are nearby?

In the area, you can enjoy a variety of outdoor activities such as skiing, mountain biking, and hiking, making it an ideal destination for adventure enthusiasts seeking memorable experiences during your stay.

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Family Activities

  • Wintergreen Resort Skiing and Snowboarding: Enjoy the thrill of hitting the slopes with family-friendly ski and snowboard runs suitable for all skill levels, right here in this popular Virginia mountain destination.
  • Nordic Skiing and Snowshoeing Trails: Explore scenic Nordic trails surrounded by winter’s beauty, offering a peaceful outdoor adventure perfect for families looking to embrace the snowy landscape.
  • Wintergreen Nature Foundation Programs: Participate in educational programs and guided nature walks designed to engage children and adults alike, highlighting the region’s natural beauty during the winter months.
  • Sleigh Rides and Scenic Lift Rides: Experience the magic of winter with memorable sleigh rides or scenic lift trips that provide stunning views of the snow-covered mountains of the area.
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Adult Activities

  • Skiing and Snowboarding: Experience exhilarating slopes at the area’s ski resorts, perfect for adult enthusiasts looking to enjoy winter sports in a scenic mountain setting.
  • Gourmet Dining and Local Wineries: Explore the region’s culinary scene by visiting fine dining establishments and local wineries that showcase the area's regional flavors during the winter months.
  • Spa and Wellness Treatments: Indulge in relaxing spa services offered at upscale resorts nearby, providing rejuvenation after outdoor adventures in the winter landscape.
  • Snowshoeing and Cross-Country Skiing: Discover peaceful trails for snowshoeing or cross-country skiing, allowing you to immerse yourself in the tranquil winter scenery of the area.

Other Places to Stay in Wintergreen Resort, VA

Pedlars Edge
Pedlars Edge Vacation Rentals
Treeloft
Treeloft Vacation Rentals
More Places to Stay Near Wintergreen Resort

Wintergreen Resort Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Explore the region’s outdoor options ahead of time to maximize your stay in this scenic destination and enjoy all that it offers.
  • Choose a Prime Location: Select vacation rentals close to popular trails or scenic spots for easy access to the area's natural beauty and activities.
  • Pack Smart and Seasonally Appropriate: Bring suitable clothing and gear to comfortably experience the area's distinct seasons, whether summer hikes or winter snowsports.
  • Engage with Local Tips and Recommendations: Take advantage of insider advice from hosts or locals to discover hidden gems and make your trip truly memorable.

Transportation Options

  • Car Rentals: Renting a car is a convenient way to explore the region at your own pace, especially with the scenic routes surrounding Wintergreen Resort in Virginia.
  • Airport Shuttles: Dedicated shuttle services connect the nearby airports to this destination, offering a hassle-free transfer for travelers arriving from afar.
  • Public Transportation: Local bus services provide an economical transportation option within the area, enabling easy access to key spots around the resort and Nellysford.
  • Taxis and Ride-Sharing: Taxis and ride-sharing apps offer flexible, on-demand transportation for quick trips around the region without the need for private vehicle rental.

Local Customs Options

  • Southern Hospitality: Visitors often experience warm welcomes and friendly gestures that reflect the region's tradition of southern hospitality in this area.
  • Embracing Appalachian folk customs, locals may participate in or observe traditional music, crafts, and storytelling unique to the region.
  • Respect for Nature: It’s customary here to show reverence for the surrounding natural beauty by practicing eco-friendly habits and engaging in outdoor conservation efforts.
  • Local Culinary Practices: Enjoying regional cuisine, you'll notice a focus on farm-to-table ingredients and locally inspired dishes common in this part of Virginia.

Frequently Asked Questions About Wintergreen Resort?

1. What are the top vacation rentals in Wintergreen Resort?

There are a lot of options in Wintergreen Resort. If you plan on staying in the Wintergreen Resort area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wintergreen Resort:

2. How many Rentbyowner vacation rentals are available in Wintergreen Resort?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 58 in the Wintergreen Resort area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Wintergreen Resort. 

3. What is the cancellation policy for vacation rentals in this region?

The cancellation policy varies depending on the individual property listing. To ensure you understand the specific conditions, please review the cancellation details provided on the listing or contact the property owner directly before booking.

4. How do I find available dates and book a vacation rental here?

You can easily check availability and make your reservation through the booking platform by selecting your preferred dates. For personalized assistance, reach out to the property owner to confirm availability and any special requirements.

5. Are there any additional fees or deposits required when booking a rental in this destination?

Additional fees such as cleaning charges or security deposits may apply depending on the property. These details will be outlined during the booking process or on the listing page—be sure to review them carefully before finalizing your reservation.

6. What amenities are typically included in vacation rentals around here?

Most properties offer amenities like Wi-Fi, fully equipped kitchens, and parking. Specific amenities are listed for each rental, so it’s best to check the individual property details for what’s included during your stay.

7. How close are these rentals to local attractions or outdoor activities?

Vacation rentals in the area are generally situated conveniently to outdoor activities and local attractions. To get precise information about proximity, refer to the listing details or contact the property owner for guidance.

Best Vacation Homes in Wintergreen Resort