Discover Your Perfect Wintergreen Rentals by Owner

Wintergreen Rentals by Owner

More Top-Rated Rentals by Owner in Wintergreen Area

Why Choose Rent By Owner for your Wintergreen vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner

Where are the best neighborhoods to stay in Wintergreen?

When planning your stay in Wintergreen, Nellysford, Virginia, exploring the diverse neighborhoods can enhance your overall experience. From peaceful mountain retreats to vibrant community areas, each neighborhood offers unique charm and easy access to the natural beauty of the region. Booking a rental by owner through Rent By Owner ensures you find a comfortable and reliable vacation home that meets your needs. Whether you prefer a quiet setting or a lively locale, the neighborhoods around Wintergreen provide the perfect backdrop for your memorable getaway in Virginia.

Treeloft

By choosing Treeloft, you gain access to a serene retreat within the area, offering a peaceful escape while remaining close to regional attractions. This neighborhood provides an ideal setting for those seeking comfortable and convenient vacation rentals in Nellysford.

View 1034+ Rentals in Treeloft

Pedlars Edge

Staying in Pedlars Edge allows you to experience the charm of this part of the region, with easy access to natural beauty and local amenities. Here, you can enjoy a dependable rental that combines comfort with the tranquility of the Virginia countryside.

View 1040+ Rentals in Pedlars Edge

Best Times to Visit Wintergreen

When should you plan your Rentals by Owner stay?

To make the most of your stay in this charming destination, consider planning your vacation during the region’s shoulder seasons when you can enjoy fewer crowds and more affordable rental options through Rent By Owner.

Peak Season Highlights

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Winter (December to February)

During the winter months, the area experiences a peak season as visitors seek cozy retreats and winter sports opportunities. Booking early ensures you secure the most desirable vacation rentals by owner for this popular time.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Summer (June to August)

The summer season attracts travelers looking to enjoy warm weather and outdoor activities. Peak demand makes it essential to book your preferred rental in advance here to avoid missing out during this lively period.

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

Off-Season Highlights

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Spring (March to May)

Spring offers a quieter escape for those seeking more affordable accommodations and fewer crowds. Planning ahead can help you find ideal rentals by owner for a rejuvenating visit here during this season.

Average Temperature Daytime: 55°F to 70°F - Nighttime: 35°F to 50°F
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Fall (September to November)

Autumn provides a peaceful setting with vibrant foliage, attracting visitors who prefer a more relaxed experience. Booking during this off-peak period ensures you enjoy the region’s natural beauty without the busy crowds.

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

Weekly Weather Forecast for Wintergreen

How to Book Your Wintergreen vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Wintergreen Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor grilling with a private barbecue area to enhance your stay.
  • Relax on spacious decks or patios offering scenic views of the surrounding mountains and forests.
  • Take advantage of outdoor fire pits for cozy evenings under the stars.
  • Benefit from access to hiking trails directly from your rental, exploring the area's natural beauty.
  • Make use of community outdoor pools or lakes available in the region for swimming and water activities.
  • Utilize dedicated outdoor parking spaces to conveniently access your vacation rental.
  • Experience the serenity of outdoor seating areas designed for enjoying the fresh mountain air and picturesque sunsets.

Top Attractions Around Wintergreen

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities and scenic experiences that showcase the natural beauty of the region, making it an ideal destination for exploration and relaxation during your stay.

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Family Activities

  • Wintergreen Resort Activities: Experience family-friendly skiing and snowboarding right here at the region's popular winter recreation destination.
  • Nature Trail Exploration: Discover scenic hiking and snowshoeing trails that offer breathtaking views and outdoor adventure suitable for all ages in the area.
  • Ice Skating at Wintergreen: Enjoy a fun-filled day on the ice rink, perfect for families seeking outdoor winter entertainment during your stay.
  • Wildlife Viewing & Nature Centers: Visit local wildlife refuges and nature centers that provide educational exhibits and opportunities to observe native animals in their winter habitats.
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Adult Activities

  • Wintergreen Resort Spa & Wellness Center: Indulge in rejuvenating spa treatments and relaxing massages designed to enhance your winter escape.
  • Snowshoeing and Cross-Country Skiing: Explore scenic trails throughout the area, offering a peaceful way to enjoy winter landscapes and get some exercise.
  • Winter Hiking Adventures: Discover well-maintained trails that provide stunning vistas and invigorating outdoor experiences during the colder months.
  • Local Wineries and Distilleries Tours: Sample regional wines and spirits at nearby establishments, enriching your visit with local flavors and craftsmanship.

Other Places to Stay in Wintergreen, VA

Pedlars Edge
Explore 1,040 Properties
Treeloft
Explore 1,034 Properties
Wintergreen Resort
Explore 44 Properties
More Places to Stay Near Wintergreen

Wintergreen Travel Tips

How Can You Make the Most of Your Stay?

  • Plan your activities ahead: Research local outdoor adventures and relaxation options in the area to make the most of your stay in this scenic destination.
  • Select a strategic rental location: Choose a property close to popular sites or natural attractions to maximize your time exploring the region.
  • Visit during the shoulder seasons: Traveling in off-peak times can offer more tranquility and better deals, enhancing your overall experience here.
  • Engage with local amenities: Take advantage of nearby shops, eateries, and services that reflect the charm of this inviting part of Virginia.

Transportation Options

  • Personal Vehicle: Having your own car offers the most flexibility to explore the scenic region around Wintergreen and access remote rental properties with ease.
  • Shuttle Services: Local shuttle options provide convenient transportation between key points within the area, making it easier to enjoy your stay without worrying about parking.
  • Taxi and Rideshare: Taxis and ride-hailing services like Uber and Lyft are available for quick, reliable trips throughout Nellysford and the surrounding region.
  • Public Transportation: Limited but accessible bus routes connect popular destinations in the area, helping you reach rental locations without the need for private transport.

Local Customs Options

  • Southern Hospitality: You’ll notice a warm and friendly approach to welcoming visitors, reflecting the region’s tradition of Southern hospitality that makes you feel at home during your stay.
  • Participating in local festivals often involves enjoying regional music, crafts, and foods that highlight this area's rich Appalachian heritage.
  • Respect for Nature: Here, there is a strong emphasis on preserving the natural beauty of the region, so you are encouraged to follow eco-friendly practices and respect outdoor spaces.
  • Community Engagement: Engaging with local traditions and supporting small businesses is highly valued, offering you an authentic experience of the area’s close-knit community.

Frequently Asked Questions About Wintergreen Rentals by Owner

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 Rentbyowner vacation rentals are available in Wintergreen?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 250 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. 

3. What is the cancellation policy for rental properties booked through Rent By Owner in Wintergreen?

The cancellation policy varies depending on the specific property listing. To ensure you understand the terms, please review the cancellation details provided in the listing or contact the property owner directly before completing your reservation.

4. How do I confirm the availability of a vacation rental by owner in this area?

Availability calendars are typically maintained by the property owners and can be viewed directly on the listing. For real-time confirmation, it’s best to reach out to the owner or use the booking platform’s messaging feature.

5. Are linens and utilities included in the rental price in this destination?

In most cases, the specifics regarding linens, utilities, and other amenities are detailed within each listing. Be sure to review these details carefully or contact the owner to clarify what is included with your booking.

6. What procedures should I follow for checking in and out of my rental in this region?

Check-in and check-out instructions are usually provided by the owner in the listing or after booking confirmation. It’s advisable to communicate directly with the owner to coordinate your arrival and departure times for a smooth stay.

7. How do I handle special requests or accommodations when booking a rental by owner here?

Most listings include a section where you can request additional amenities or accommodations. For specific requests, contact the property owner in advance to ensure they can accommodate your needs and to confirm any possible additional charges.

More Rentals You May Like Near Wintergreen

More Top-Rated Rentals by Owner in Wintergreen Area