Discover Your Perfect Wintergreen Vacation Homes

Best Vacation Homes in Wintergreen

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Wintergreen Pet Friendly Vacation Rentals

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Wintergreen Large Vacation Homes

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Why Choose Rent By Owner for your Wintergreen 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 Vacation Rentals

Where are the best neighborhoods to stay in Wintergreen?

When exploring your options for a memorable getaway, consider neighborhoods in Wintergreen that offer the perfect blend of natural beauty and convenient amenities. Located near Nellysford, these areas provide easy access to outdoor recreation, scenic views, and charming local attractions. Whether you prefer a peaceful retreat or an active adventure, staying in this part of Virginia allows you to enjoy a authentic experience surrounded by the region’s picturesque landscapes. Choose a well-suited neighborhood to ensure your stay is both comfortable and seamlessly connected to everything this beautiful area has to offer.

Treeloft

Nestled within the scenic surroundings of this area, Treeloft offers an inviting retreat with easy access to outdoor activities and peaceful landscapes. It’s an ideal choice for those seeking a comfortable stay in the heart of Nellysford.

View 1034+ Rentals in Treeloft

Pedlars Edge

Located in a tranquil part of the region, Pedlars Edge provides a perfect base for exploring the natural beauty and serene environment of Nellysford. This neighborhood is great for travelers wanting a relaxing escape with convenient amenities nearby.

View 1040+ Rentals in Pedlars Edge

Best Times to Visit Wintergreen

When should you plan your Vacation Rentals stay?

Determining the optimal time to visit here can enhance your experience, allowing you to enjoy the region's unique seasonal charm while making the most of your stay in this picturesque destination.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination offers ideal conditions for enjoying the snowy landscape and winter sports. The region's brisk daytime temperatures and chilly nights create a cozy atmosphere for your stay.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Fall (September to November)

Autumn is a popular time here due to the stunning fall foliage and mild weather, making it perfect for outdoor exploration. Visitors often flock to experience the scenic views and vibrant colors of the season.

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

Off-Season Highlights

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Spring (March to May)

Spring brings milder temperatures and blooming scenery, offering a quieter experience before the busy summer months. It’s an excellent time to enjoy outdoor activities with fewer crowds.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F
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Summer (June to August)

During summer, the area experiences warm weather ideal for outdoor recreation and relaxation. This season sees fewer visitors compared to other peak times, providing a more tranquil getaway.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Wintergreen

How to Book Your Wintergreen 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

More Top-Rated Vacation Rentals in Wintergreen 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 hiking trails right outside your rental, allowing you to explore the region's natural beauty.
  • Relax in a private outdoor hot tub or Jacuzzi that offers stunning views of the surrounding mountains.
  • Make the most of the season with a cozy fireplace or fire pit for evening gatherings under the stars.
  • Take advantage of outdoor dining areas, perfect for savoring meals while soaking in the fresh mountain air.
  • Utilize spacious decks or patios equipped with loungers and seating to unwind and enjoy the outdoors.
  • Benefit from on-site tennis courts or other sports facilities for active pursuits during your stay.
  • Use outdoor grills or BBQ stations available at many rentals for delicious cookouts amid nature.

Top Attractions Around Wintergreen

What attractions are nearby?

During your stay, you can enjoy a variety of outdoor activities nearby, including hiking, mountain biking, and scenic overlooks that showcase the beauty of this region's natural landscape.

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Family Activities

  • Wintergreen Resort Skiing and Snowboarding: Experience the thrill of winter sports with family-friendly slopes that offer fun for all skill levels, making it a must-try activity during your stay.
  • Walking and Biking Trails: Explore scenic trails throughout the area that are perfect for family walks or bike rides, allowing you to enjoy the natural beauty of this mountain destination.
  • Wintergreen Nature Foundation Programs: Engage in educational nature programs and outdoor activities designed for families seeking to learn about the region’s environment and wildlife.
  • Local Arts and Craft Events: Visit nearby galleries and craft markets that showcase local artisans, offering family-friendly activities and opportunities to create lasting memories together.
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Adult Activities

  • Wintergreen Resort Golf Course: Spend a day indulging in world-class golf amidst stunning mountain vistas, perfect for both beginners and seasoned players looking to enjoy the scenic beauty of the area.
  • Hiking and Nature Trails: Explore the extensive network of trails that wind through the region, offering breathtaking views and a peaceful escape into nature's serenity.
  • Winter Sports Activities: Take advantage of the winter season with skiing, snowboarding, or snowshoeing at local resorts that cater to all skill levels.
  • Nelson County Distilleries and Wineries: Discover the locally crafted spirits and wines through tasting tours, providing a taste of the area's vibrant artisan culture.

Other Places to Stay in Wintergreen, VA

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

Wintergreen Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the region’s natural beauty by engaging in outdoor pursuits like hiking, biking, or scenic drives to fully enjoy this destination’s picturesque landscapes.
  • Visit Seasonal Events and Festivals: Check the calendar for local events that showcase the area's vibrant community spirit and unique traditions during your stay.
  • Plan Your Dining Experiences: Discover nearby restaurants and eateries offering regional cuisine to enrich your culinary journey here.
  • Utilize Personalized Recommendations: Reach out to your hosts or local guides for insider tips on hidden gems and must-see spots to enhance your visit here.

Transportation Options

  • Personal Vehicles: Driving your own car is the most flexible way to explore here, with ample parking available near many vacation rentals and attractions within the region.
  • Shuttle Services: Several local shuttle providers offer convenient transportation between popular destinations and lodging options in this destination.
  • Taxi and Rideshare: Taxis and rideshare companies operate throughout the area, providing reliable and quick transport options for visitors staying in nearby vacation rentals.
  • Public Transit: While limited, some regional bus services connect key points of interest and lodging locations, offering an economical choice for exploring the region.

Local Customs Options

  • Appalachian Trail Etiquette: When exploring the area's scenic trails, it is customary to keep to designated paths and leave no trace to preserve the natural beauty of this outdoor destination.
  • Local Craftsmanship: Supporting regional artisans by purchasing handmade crafts and souvenirs reflects the region’s proud tradition of craftsmanship and community spirit.
  • Mountain Hospitality: Greeting neighbors and fellow visitors with warmth and friendliness embodies the welcoming nature characteristic of this popular mountain retreat.
  • Seasonal Celebrations: Participating in local festivals and seasonal events highlights the area's cultural heritage and enhances your authentic experience here.

Frequently Asked Questions About Wintergreen?

1. What are the top vacation rentals in Wintergreen?

There are a lot of options in Wintergreen. If you plan on staying in the Wintergreen 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:

2. How many vacation rentals have private pools in Wintergreen?

There are 7 vacation rentals with private pools near Wintergreen. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Wintergreen are best for families?

If you are looking for a family-friendly vacation home in Wintergreen, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wintergreen:

4. How many Rentbyowner vacation rentals are available in Wintergreen?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 501 in the Wintergreen 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. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policies vary depending on the specific property you choose. It’s best to review the individual listing details or contact the property owner directly to understand their refund and cancellation terms.

6. Are there any additional fees when booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes may apply based on the property. Be sure to check the listing details for a clear breakdown of all costs before completing your booking.

7. How do I ensure my reservation is secure and confirmed?

Reservations are typically secured through the booking platform after payment is completed. Verify that the property owner has confirmed your reservation and review the confirmation email for accuracy and details.

8. Is it possible to modify or cancel my booking if plans change?

Modification or cancellation options depend on the property's policies. Contact the property owner directly through the platform to discuss any changes or cancellations and to confirm the applicable rules.

9. What amenities can I expect at vacation rentals in the region?

Amenities vary by property but often include essentials like Wi-Fi, full kitchens, outdoor spaces, and parking. Check the specific listing for a comprehensive list of amenities available at your chosen property.

Wintergreen Top Rated Vacation Rentals

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