Discover Your Perfect Windsor Vacation Homes

Windsor Luxury Rentals

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Windsor Pet Friendly Vacation Rentals

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Windsor Large Vacation Homes

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9.0 (188 Reviews)
Bed & Breakfast
The Grape Leaf Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Windsor 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.

Best Times to Visit Windsor

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit ensures you can fully enjoy all that the area has to offer, whether you're seeking warm weather, vibrant local events, or a quieter escape in this destination’s scenic surroundings.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll enjoy ideal weather for exploring the region’s outdoor activities and vineyards.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 60°F
autumn
Fall (September to November)

The early fall brings pleasant temperatures and vibrant fall foliage, perfect for sightseeing and relaxing in your vacation rental.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

This quieter season offers cooler weather with fewer tourists, ideal if you're seeking a peaceful retreat in this destination.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 45°F
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Early Spring (March to May)

As the region awakens from winter, the mild temperatures and blooming landscapes create a charming setting for your stay.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 50°F

Weekly Weather Forecast for Windsor

How to Book Your Windsor 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

More Top-Rated Vacation Rentals in Windsor 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 with a private patio or barbecue grill available for your use.
  • Take advantage of beautifully landscaped gardens and lush green spaces surrounding your rental.
  • Relax by an outdoor swimming pool, perfect for cooling off during warmer days in the region.
  • Make the most of a spacious yard ideal for outdoor activities or family gatherings.
  • Experience scenic views from a private balcony or sun deck overlooking the area.
  • Utilize well-maintained walking trails or bike paths that showcase the natural beauty of the region.
  • Unwind in a cozy fire pit for evening relaxation under the stars, common at many properties here.

Top Attractions Around Windsor

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities and scenic spots that showcase the natural beauty of this destination, making your stay in Windsor, California, an enjoyable and memorable experience.

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Family Activities

  • Safari West Wildlife Preserve: Immerse your family in an exciting safari adventure right here, offering a chance to see exotic animals in their naturalistic habitats.
  • Windsor Town Green: Enjoy outdoor activities and community events at this central hub, perfect for picnics and family gatherings in the region.
  • California Discovery Museum: Engage with interactive exhibits and hands-on science displays that make learning fun for children visiting the area.
  • Annadel State Park: Explore scenic hiking and biking trails through lush landscapes, ideal for active families seeking outdoor recreation nearby.
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Adult Activities

  • Windsor Golf Club: Enjoy a round of golf on the scenic courses that attract enthusiasts seeking a relaxing day in the region.
  • Vineyard Tours and Tasting Rooms: Explore local vineyards to experience the region's renowned wines, perfect for wine lovers looking to indulge during their stay.
  • The Windsor Town Green: Attend community events or simply unwind in this charming area packed with local shops, cafes, and cultural happenings.
  • Hiking and Nature Trails: Discover outdoor adventures through trails that meander through the area's natural beauty, ideal for those wanting to immerse themselves in the local landscape.

Other Places to Stay in Windsor, CA

Powell's Sweet Shoppe - Windsor
Powell's Sweet Shoppe - Windsor Vacation Rentals
Dom Whitney Tasting Lounge
Dom Whitney Tasting Lounge Vacation Rentals
Windsor Golf Club
Windsor Golf Club Vacation Rentals
Pacific Coast Air Museum
Pacific Coast Air Museum Vacation Rentals
Windsor Oaks Vineyards
Windsor Oaks Vineyards Vacation Rentals
Martinelli Vineyard
Martinelli Vineyard Vacation Rentals
Sonoma-Cutrer Vineyards Cutrer Vineyard
Sonoma-Cutrer Vineyards Cutrer Vineyard Vacation Rentals
Russian Hill Estate Vineyards
Russian Hill Estate Vineyards Vacation Rentals
More Places to Stay Near Windsor

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Seasons: Visiting during less busy times allows you to enjoy a more relaxed experience and better availability of desirable vacation rentals in this region.
  • Explore Local Dining and Wineries: Indulge in the area’s renowned culinary scene and wine tasting experiences to make your stay truly memorable.
  • Take Advantage of Recreational Activities: Engage in outdoor pursuits such as cycling or hiking within close proximity to your rental to maximize your time here.
  • Book Your Accommodation Early: Secure your preferred vacation rentals well in advance to ensure a seamless and enjoyable visit to this destination.

Transportation Options

  • Windsor Transit System: This local bus service offers convenient routes throughout the area, making it easy to explore your surroundings without the need for a car.
  • Rideshare Services: Popular apps like Uber and Lyft operate here, providing flexible transportation options to quickly reach your vacation rental or nearby attractions.
  • Taxi Services: Traditional taxi companies are available in the region, offering reliable point-to-point transportation for added convenience during your stay.
  • Car Rentals: Multiple rental agencies serve the area, giving you the freedom to explore nearby scenic spots and destinations at your own pace.

Local Customs Options

  • Wine Tasting Etiquette: When visiting local wineries, it’s customary to sample wines responsibly and appreciate the region’s renowned viticulture culture.
  • Farmers' Market Traditions: Supporting the area’s agricultural community by purchasing fresh produce at farmers' markets is a valued local custom in this destination.
  • Community Festivals: Participating in seasonal festivals and local celebrations allows you to experience the region’s vibrant cultural heritage firsthand.
  • Respect for Nature: Maintaining a respectful attitude towards the area's parks and natural reserves ensures their preservation for future visitors to enjoy.

Frequently Asked Questions About Windsor?

1. What are the top vacation rentals in Windsor?

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

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

There are 66 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 595 in the Windsor 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. 

5. What is the cancellation policy for vacation rentals in Windsor, California?

The cancellation policy varies depending on the specific property you select. You should review the individual listing details or contact the property owner directly to understand the terms and any applicable fees before completing your booking.

6. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning fees, service charges, or security deposits are often listed within the property details. It's recommended to read the full listing or reach out to the host for clarification on any extra costs involved.

7. How do I know if a vacation rental in Windsor meets my needs?

You can check the detailed descriptions, amenities, and photos provided in each listing to determine if it matches your preferences. Contact the property owner with any specific questions or requirements to ensure it’s the right fit for your stay.

8. What is the process for confirming and paying for my booking in this area?

Once you select your preferred property, you'll follow the booking procedure on the platform, which typically involves confirming your dates and making a secure payment. Payment methods and confirmation details will be provided after your reservation is completed.

9. Are there specific check-in and check-out times I need to follow in Windsor vacation rentals?

Check-in and check-out times vary between properties. These details are provided in each listing, and you may also communicate directly with the host to arrange convenient times for your arrival and departure.

Windsor Top Rated Vacation Rentals

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