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Windsor vacation rentals

We found 1,031 vacation rentals — enter your dates for availability

Select from 30 houses, 28 condos, and other vacation rentals to find the perfect place for your stay in Windsor. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Windsor

Showing deals for:Mar 6 - Mar 13

Image gallery for Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Pool
10 out of 10, Exceptional, (66 reviews)
Exceptional
(66 reviews)

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg, CA

13% off
Price is $1,917
$13,421 for 7 nights
All fees included
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

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Find out more about Windsor

Why visit Windsor

  • Outdoor Adventures: Windsor is perfect for outdoor enthusiasts with scenic parks and opportunities for hiking and biking.
  • Charming Atmosphere: The quaint piazza and friendly neighborhoods create a romantic and relaxing getaway.
  • Family-Friendly Activities: Enjoy a variety of activities suitable for families, making it an ideal destination for all ages.
  • Local Wineries: Explore nearby wineries and indulge in wine tasting experiences unique to the region.
  • Diverse Accommodation: Choose from cozy vacation homes, charming cottages, and stylish apartments for a comfortable stay.

Popular types of accommodation in Windsor

If you're exploring Windsor for your next getaway, you're in luck. The most popular types of vacation rentals here include cozy Houses, charming Cottages, and stylish Apartments. Whether you're searching for house rentals in Windsor or a comfortable home to unwind in, our diverse selection of vacation homes ensures you'll find the perfect fit for your stay.

  • Houses: The top choice for travelers in Windsor, these spacious homes offer a comfortable and private retreat for families and groups.
  • Cottages: Charming and cozy, cottages provide a quaint escape for those seeking a peaceful stay surrounded by nature.
  • Apartments: Ideal for solo travelers or couples, apartments offer a convenient and stylish way to enjoy your time in Windsor.
  • Cabins: Rustic and inviting, cabins are perfect for those wanting a unique experience in the heart of the outdoors.
  • Villas: Luxurious and spacious, villas provide an upscale option for travelers looking for elegance and comfort.**

Top attractions near Windsor

Windsor, California, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering beautiful scenery and a variety of attractions. Visitors can explore the charming piazza, enjoy the tranquil river, and relax at nearby beaches. The area's points of interest cater to culture seekers and families alike, making it a delightful destination for everyone looking to unwind and connect with nature.

  • Russian River: This picturesque river, located 2 miles from Windsor, offers stunning scenery and a chance for outdoor adventures like kayaking and hiking along its banks, perfect for nature lovers.
  • Healdsburg Plaza: Located 5 miles away, this vibrant town square is a cultural hub with charming shops, restaurants, and frequent events, making it ideal for immersing yourself in local city vibes.
  • Charles M. Schulz Museum: Situated 7 miles from Windsor, this museum pays tribute to the beloved Peanuts creator, featuring exhibits on his life and art, perfect for fans of comic culture.

Things to do recommended for couples

Searching for a romantic getaway in Windsor? Visit the enchanting Russian River Vineyard for wine tasting, embark on an adventure with Rubicon Adventures on the water, or enjoy a playful round at Pee Wee Golf and Arcade. Experience the perfect mix of romance and fun.

Things to do recommended for families

During your family vacation in Windsor, California, enjoy sweet treats at Powell's Sweet Shoppe, relax at Spring Lake Park just 11 miles away, and have fun ice skating at the Redwood Empire Ice Arena located 7 miles from Windsor. Perfect for creating lasting memories together.

Things to do recommended for groups

Immerse yourselves in culture at the Luther Burbank Center for the Arts, enjoy outdoor adventures at Bohemian Grove, or challenge each other at the Healdsburg Golf Club. Each destination offers a unique experience for group travelers looking to create memorable moments together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windsor

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these features and more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that both you and your pet feel completely at home.
  • Planning for a long term stay visiting Windsor: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider additional amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Windsor

Windsor, California, is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway. With its sunny weather and friendly atmosphere, visitors can enjoy family-friendly activities, scenic parks, and charming neighborhoods. Nearby regions offer excursions and relaxation, making it the perfect spot for a memorable vacation. Whether you're exploring local wineries or taking leisurely strolls, Windsor promises a delightful experience for every traveler.

  • Santa Rosa: Santa Rosa is a vibrant city located 9 miles from Windsor, known for its beautiful outdoor spaces and family-friendly atmosphere. Visitors can enjoy various activities such as golfing at scenic courses, indulging in body treatments at local spas, and exploring the picturesque riverfront. The city boasts attractions like event conference venues and nearby beaches, making it a great spot for both relaxation and adventure. With its blend of urban and natural experiences, Santa Rosa promises an unforgettable getaway.
  • Healdsburg: Just 5 miles from Windsor, Healdsburg is a charming city that captures the essence of California's wine country. Its romantic ambiance and stunning scenery make it a popular destination for couples and outdoor enthusiasts alike. Visitors can unwind in recreational areas, enjoy rejuvenating spa treatments, and take in the beauty of the local rivers and piazza square. Healdsburg's vibrant dining scene and boutique shops add to its appeal, making it perfect for a leisurely day of exploration.
  • Chalk Hill: Located a mere 2 miles from Windsor, Chalk Hill is a hidden gem for wine lovers and outdoor seekers. Known for its picturesque wineries, this area offers a serene and romantic experience amidst beautiful landscapes. Visitors can explore the local rivers and enjoy the tranquil surroundings. With its focus on outdoor activities and scenic views, Chalk Hill invites travelers to relax and savor the natural beauty of Sonoma County.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and October, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January48.2°F (9.0°C)Light RainMostly SunnySlightly LowSlightly Low
February49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
March51.1°F (10.6°C)Light RainMostly SunnyAverageSlightly Low
April55.6°F (13.1°C)No Rain (Dry)Mostly SunnyAverageAverage
May60.6°F (15.9°C)No Rain (Dry)SunnyAverageSlightly High
June67.3°F (19.6°C)No Rain (Dry)SunnySlightly HighAverage
July69.8°F (21.0°C)No Rain (Dry)SunnySlightly HighAverage
August69.4°F (20.8°C)No Rain (Dry)SunnyAverageAverage
September68.0°F (20.0°C)No Rain (Dry)SunnyAverageSlightly High
October62.1°F (16.7°C)No Rain (Dry)SunnySlightly HighSlightly High
November53.1°F (11.7°C)Light RainMostly SunnySlightly LowAverage
December47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save money on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. Also, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, feel free to use our filters to narrow your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin your savings journey.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or effortlessly view and organize your travel plans. You can easily access properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Windsor

The area's wineries and festivals are just a few of the reasons to vacation in Windsor. This welcoming city is known for its restaurants, bird watching and hiking. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windsor

Are you searching for attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Windsor has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Kendall-Jackson Winery (3.6 mi / 5.9 km)
  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Russian River Vineyard (6.7 mi / 10.8 km)
  • Jordan Vineyard & Winery (7.6 mi / 12.3 km)
  • Korbel Winery (8.5 mi / 13.7 km)
  • Dry Creek Vineyard (9.4 mi / 15.1 km)

Exploring the natural landscape of Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Russian River (2.3 mi / 3.7 km)
  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Safari West (6.6 mi / 10.6 km)
  • Laguna de Santa Rosa (7.1 mi / 11.5 km)
  • Old Courthouse Square (9.2 mi / 14.9 km)
  • Luther Burbank Home and Gardens (9.5 mi / 15.3 km)

Traveling to and around Windsor

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 2.6 mi (4.2 km) from the city center.

Frequently asked questions

What is the best area to stay in Windsor when booking a vacation rental?
When booking a vacation rental in Windsor, California, one of the best areas to consider is the charming downtown district. This area offers a vibrant atmosphere with a variety of shops, restaurants, and local cafes, making it an ideal spot for those who enjoy being in the heart of the action. Visitors can easily explore the Windsor Town Green, a lovely park that hosts community events, farmers' markets, and concerts throughout the year. The Green is also surrounded by beautiful walking paths, superb for leisurely strolls.

Another excellent option is the surrounding wine country. Staying in this area places you close to some of Sonoma County's finest wineries, allowing you to indulge in wine tastings and vineyard tours. The scenic views of rolling hills and vineyards provide a picturesque backdrop, making it an unforgettable experience for wine enthusiasts. There are numerous vacation rental properties available in both the downtown and wine country areas, giving you a variety of choices to suit your preferences.
How much does it cost to rent a vacation home in Windsor?
Prices for vacation rentals in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windsor vacation house rentals?
You can find great discounts on house rentals in Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Windsor?
For renting a beach house in Windsor, California, travelers should consider the nearby coastal towns of Bodega Bay and Jenner, which are approximately 20-30 minutes away by car. Bodega Bay offers a selection of vacation rentals that provide stunning views of the Pacific Ocean, with many properties featuring spacious decks, outdoor grills, and hot tubs for post-beach relaxation. The area is known for its charming waterfront and proximity to local seafood restaurants, making it a delightful spot for food lovers.

In Jenner, visitors can find cozy cottages located along the Russian River, where the river meets the ocean. These rentals often include amenities like kayaks or canoes for exploring the river, outdoor fire pits, and easy access to scenic hiking trails in nearby parks. The natural beauty of the coastline and the tranquility of the river create a great setting for a relaxing getaway.

Additionally, the nearby Sonoma Coast State Park offers breathtaking vistas and opportunities for hiking, picnicking, and beachcombing. Many rentals in the area provide beach access or are just a short drive from pristine beaches, allowing travelers to enjoy both the river and ocean experience while having modern conveniences such as Wi-Fi and fully equipped kitchens.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, vacation houses are the most popular type of rental, with about 32 available throughout the area. These houses typically offer spacious living arrangements, multiple bedrooms, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups looking to enjoy the beautiful surroundings. Additionally, there are around 22 condos available, which usually feature modern amenities, communal pools, and close proximity to local attractions like the Windsor Town Green and nearby vineyards. Several apartments and villas can also be found, providing cozy options for those seeking a more compact stay.
Are there any family house rentals in Windsor?
In Windsor, California, there is a wide selection of family-friendly house rentals available, with around 47 options to choose from. The charming neighborhoods here provide an inviting space for families, often featuring spacious living areas and fully equipped kitchens ideal for preparing meals together. Many properties also come with outdoor spaces, such as patios or gardens, great for kids to play and for families to enjoy gatherings.

Visitors will appreciate the close proximity to local attractions, including the scenic Windsor Town Green, which hosts community events and has playgrounds for children. Additionally, the area is near vineyards and parks that offer opportunities for outdoor activities like hiking and picnicking. See all family-friendly rentals in Windsor.
Can I rent a vacation home with a pool or hot tub in Windsor?
In Windsor, California, there are several vacation homes available for rent that feature pools and hot tubs, with around 36 options to choose from. This charming area in Sonoma County is known for its picturesque vineyards and serene landscapes, making it a great destination for relaxation. Travelers can expect many amenities in these rentals, including private swimming pools, luxurious hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens great for preparing meals after a day of exploring the region. Some properties may also include features such as barbecue grills and beautiful gardens, enhancing the overall vacation experience. Find your rental in Windsor with a pool or a hot tub.
Can I find long-stay vacation rentals in Windsor?
A long-stay vacation rental in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Windsor?
In Windsor, there are numerous pet-friendly house rentals available, making it a great destination for travelers looking to bring their furry friends along. Many of these homes come equipped with spacious backyards, superb for pets to roam freely, as well as amenities such as modern kitchens, cozy living areas, and sometimes even outdoor patios for enjoying the pleasant California weather.

Windsor is situated near several parks and scenic areas, providing excellent opportunities for outdoor activities with pets. The nearby Windsor Town Green is a lovely spot for leisurely walks and community events, while the beautiful Russian River offers opportunities for hiking and exploring nature. Additionally, the surrounding vineyards and wineries often have outdoor spaces that welcome pets, allowing you to enjoy wine tastings while your pet relaxes by your side. See all pet-friendly rentals in Windsor.
Are there any remote work vacation rentals in Windsor?
In Windsor, California, there are a variety of remote work vacation rentals available, with about 61 options suiting those seeking a productive getaway. Travelers can expect properties equipped with essential amenities like high-speed Wi-Fi, dedicated office spaces including desks, chairs, and even computer monitors, creating an ideal environment for working remotely.

Windsor is situated in the beautiful Sonoma County wine region, offering a peaceful setting with scenic views and easy access to local vineyards. Many rentals feature spacious living areas and outdoor spaces, great for taking breaks or enjoying a glass of local wine after a day's work. Additionally, the area boasts parks and walking trails, providing opportunities for relaxation and recreation during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windsor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windsor?
In Windsor, popular vacation rental amenities include WiFi, which allows guests to stay connected, and fully equipped kitchens that enable travelers to prepare their own meals. Many rentals also feature coffee and tea makers for quick morning brews and blenders for those who enjoy smoothies or other blended drinks. Additionally, several properties offer access to pools, providing a refreshing spot to relax and unwind.
When is the best time to visit Windsor for a vacation rental?
The best time to visit Windsor for a vacation rental is during the peak season from August to October, with October being particularly popular. This time of year is ideal for those seeking a blend of outdoor activities and local culture, as the comfortable temperatures (ranging from the low 50s to mid-70s Fahrenheit) invite visitors to explore the beautiful vineyards and scenic trails in the area.

As the summer sun begins to mellow in October, you can enjoy the renowned Sonoma County Harvest Fair, which showcases the region's rich agricultural heritage. This festival is a fantastic opportunity for food and wine enthusiasts to savor local wines and gourmet cuisine while mingling with fellow travelers. The vibrant fall colors also enhance the landscape, making it a picturesque time for leisurely strolls or bike rides through the vineyards.

For those looking for a more budget-friendly option, visiting in November can be a great choice. This month typically sees fewer tourists, allowing for a more tranquil experience while still enjoying the beauty of the region. The cooler temperatures provide a cozy atmosphere, great for indulging in wine tastings and exploring the charming downtown area.

Ultimately, your decision on when to visit Windsor will depend on your preference for lively events and socializings during peak season or a quieter escape to enjoy the local scenery and tastes at a more relaxed pace.
How early should I book a Windsor vacation rental?
Book your Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor?
In Windsor, visitors can enjoy a range of attractions centered around its charming downtown and surrounding natural beauty. The Windsor Town Green serves as a community hub, hosting events, farmers' markets, and concerts, making it a lively spot to explore. Nearby, the Russian River offers opportunities for kayaking and riverfront picnics, while the scenic vineyards of Sonoma County invite wine enthusiasts to partake in tastings and tours.

For those interested in outdoor activities, nearby parks like Foothill Regional Park feature hiking trails and picnic areas, providing a great backdrop for nature lovers. Additionally, the area is conveniently located near the larger city of Santa Rosa, where travelers can find more shopping, dining, and cultural experiences, including the Charles M.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windsor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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