Discover Your Perfect Windsor Oaks Vineyards Vacation Homes

Best Vacation Homes in Windsor Oaks Vineyards

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10.0 (1 Review)
House
Healdsburg Luxury
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Windsor Oaks Vineyards 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 Windsor Oaks Vineyards Vacation Rentals

Where are the best neighborhoods to stay in Windsor Oaks Vineyards?

When choosing a neighborhood to stay in Windsor Oaks Vineyards, you'll find a charming and tranquil setting that offers convenient access to the scenic beauty and local amenities of Windsor, California. This area provides a perfect backdrop for relaxation, whether you're exploring nearby vineyards or enjoying the peaceful streets. Staying in this desirable neighborhood ensures a comfortable and enjoyable visit, with easy connectivity to the natural landscape and welcoming community atmosphere that make Windsor a memorable destination for your getaway.

Roseland

This neighborhood offers a quiet residential setting with convenient access to local shops and parks, making it an ideal choice for those seeking a peaceful stay in the area around Windsor Oaks Vineyards.

View 219+ Rentals in Roseland

Wright Area Action Group

Staying nearby provides easy access to community amenities and a friendly neighborhood atmosphere, perfect for travelers looking to immerse themselves in the local region surrounding Windsor.

View 151+ Rentals in Wright Area Action Group

Southwest Santa Rosa

Located in a vibrant part of the city, this area boasts proximity to scenic spots and local attractions, enhancing your experience when exploring the region around Windsor Oaks Vineyards.

View 133+ Rentals in Southwest Santa Rosa

Riebli-Wallace Neighborhood Group

With its charming streets and welcoming community, this neighborhood offers a comfortable base for discovering the best of what the surrounding region has to offer.

View 155+ Rentals in Riebli-Wallace Neighborhood Group

North Junior College Neighborhood Association

Ideal for visitors interested in educational and cultural experiences, this neighborhood is close to key local facilities within the broader area of Windsor.

View 343+ Rentals in North Junior College Neighborhood Association

West Junior College

This part of town provides convenient access to academic institutions and scenic environs, making it a practical choice for travelers exploring the nearby vineyards and countryside.

View 360+ Rentals in West Junior College

Scenic Brush Creek

Set along a picturesque waterway, staying here offers a tranquil environment with natural beauty, ideal for nature lovers visiting the region around Windsor Oaks Vineyards.

View 298+ Rentals in Scenic Brush Creek

Junior College Neighborhood Association

Offering a blend of community charm and accessibility, this neighborhood is well-positioned for those wanting to enjoy the attractions and scenery of the surrounding region.

View 355+ Rentals in Junior College Neighborhood Association

Best Times to Visit Windsor Oaks Vineyards

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here depends on your desire for pleasant weather and fewer crowds, allowing you to fully enjoy the region's scenic beauty and peaceful ambiance during your stay.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During late spring and early summer, this destination experiences warm days perfect for enjoying the local vineyards and outdoor activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 50°F to 55°F
autumn
Fall Harvest (September to October)

The fall harvest season draws visitors seeking to experience the region's famous grape harvest and wine-tasting events, making it a vibrant time to visit.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

Winter months bring cooler weather and fewer tourists, offering a peaceful setting to explore the area’s scenic vineyards at a leisurely pace.

Average Temperature Daytime: 55°F to 60°F - Nighttime: 40°F to 45°F
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Early Spring (March to April)

In early spring, the region starts to awaken with budding vines and milder weather, providing a quiet and serene atmosphere for those seeking tranquility.

Average Temperature Daytime: 60°F to 65°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Windsor Oaks Vineyards

How to Book Your Windsor Oaks Vineyards 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 Windsor Oaks Vineyards

More Top-Rated Vacation Rentals in Windsor Oaks Vineyards 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 outdoor dining spaces perfect for savoring local wines and regional cuisine.
  • Relax in private patios or courtyards that offer scenic views of the vineyard surroundings.
  • Make the most of spacious gardens ideal for morning walks or sunset viewing.
  • Take advantage of outdoor seating areas designed for social gatherings with friends and family.
  • Benefit from accessible parking and designated outdoor parking spots for convenience.
  • Explore nearby walking trails that showcase the natural beauty of this renowned region.
  • Unwind in outdoor lounge areas equipped with comfortable furniture to enjoy the fresh air.

Top Attractions Around Windsor Oaks Vineyards

What attractions are nearby?

In this charming region, you can enjoy a variety of activities such as exploring scenic vineyards, tasting local wines, and taking leisurely walks through picturesque countryside just minutes from your vacation rental.

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Family Activities

  • Wine Tasting Tours: Experience family-friendly wine tasting tours that offer a gentle introduction to the region’s renowned vineyards, suitable for visitors of all ages.
  • Scenic Nature Walks: Embark on relaxing nature walks through the picturesque landscapes surrounding here, perfect for exploring with children or taking a peaceful break as a family.
  • Local Farmers Markets: Visit nearby farmers markets to enjoy fresh produce and artisanal goods, providing a fun and educational outing for kids and adults alike.
  • Picnic Areas in Vineyards: Take advantage of scenic picnic spots within vineyard settings, ideal for families wanting to unwind and soak in the beautiful surroundings of this destination.
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Adult Activities

  • Wine Tasting Tours: Explore the renowned vineyards with guided wine tasting experiences that showcase the region’s finest wines.
  • Vineyard Walks: Stroll through lush grapevines and enjoy the scenic beauty of this picturesque destination in the region.
  • Gourmet Dining: Indulge in exceptional local cuisine at nearby wineries and upscale eateries highlighting the area's culinary delights.
  • Private Wine Cellar Visits: Gain exclusive access to private wine cellars for an intimate look at winemaking craftsmanship here.

Windsor Oaks Vineyards Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local vineyards and wineries: Take advantage of the region’s renowned wine country by participating in tastings and vineyard tours right from your accommodation here.
  • Visit nearby outdoor attractions: Enjoy the scenic beauty of open spaces and parks to enhance your stay in this picturesque part of California.
  • Discover culinary delights: Savor farm-to-table dining experiences that showcase the fresh, local ingredients characteristic of the area.
  • Plan your transportation in advance: Arrange reliable transportation options to easily explore the region’s charming towns and hidden gems during your visit.

Transportation Options

  • Car Rentals: Renting a vehicle provides the flexibility to explore Windsor Oaks Vineyards and the surrounding region at your own pace.
  • Local Shuttle Services: Convenient shuttle options are available for traveling comfortably between key points within Windsor and nearby attractions.
  • Public Transit: Buses serve the area, offering an economical way to get around Windsor Oaks Vineyards and connect to other parts of the region.
  • Taxi and Rideshare Services: Reliable taxi and rideshare options allow for quick transportation within Windsor and to nearby destinations in the region.

Local Customs Options

  • Wine Tasting Etiquette: When visiting local vineyards, you are encouraged to sample wines responsibly and show appreciation for the winemakers' craftsmanship.
  • Local Greeting Customs: A friendly nod or handshake is common when engaging with residents or vineyard staff here, reflecting the warm hospitality of the area.
  • Dress Code for Events: Casual yet polished attire is typical for vineyard visits and outdoor gatherings, aligning with the relaxed yet refined vibe of this destination.
  • Environmental Respect: It’s customary to keep the region clean by disposing of waste properly and respecting the lush vineyards and natural surroundings.

Frequently Asked Questions About Windsor Oaks Vineyards?

1. What are the top vacation rentals in Windsor Oaks Vineyards?

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

2. How many Rentbyowner vacation rentals are available in Windsor Oaks Vineyards?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 160 in the Windsor Oaks Vineyards 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 Windsor Oaks Vineyards. 

3. What is the cancellation policy for booking vacation rentals in Windsor Oaks Vineyards?

The cancellation policy varies depending on the specific property you select. To review the exact terms, including any applicable fees or restrictions, please refer to the listing details or contact the property owner directly.

4. How do I ensure my booking in Windsor Oaks Vineyards is secure and reliable?

Booking through a trusted platform ensures security and reliability. For each rental, verify the reviews and ratings, and communicate directly with the host if you have any questions about the property or the booking process.

5. Are there any special requirements or house rules for staying in this region's vacation rentals?

Each property may have its own set of house rules or requirements, such as minimum stay durations or deposit policies. Detailed information can be found on the individual listing or by reaching out to the property owner.

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

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities. For specific features available at a particular rental, please consult the listing description or contact the host directly.

7. How far in advance should I book my stay in Windsor Oaks Vineyards during peak seasons?

To secure your preferred dates during busy times, it’s recommended to book several months ahead. Availability can vary, so checking early helps ensure a smooth reservation process.

Best Vacation Homes in Windsor Oaks Vineyards

|
10.0 (1 Review)
House
Bird and Barrel Vineyard Farmhouse
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
View Availability