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Windsor vacation rentals

We found 1,059 vacation rentals — enter your dates for availability

Select from 30 houses, 25 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:May 29 - Jun 5

Image gallery for 5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

LIC24-0669.Max 12 guests. Quiet hours 9 pm - 7 am. No outdoor amplified sound.
10 out of 10, Exceptional, (196 reviews)
Exceptional
(196 reviews)

5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

Healdsburg

7% off
Price is $2,312
$16,184 for 7 nights
All fees included
5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

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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:

  • Windsor Golf Club (1.5 mi / 2.4 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)
  • Ridge Vineyards - Lytton Springs (8.6 mi / 13.8 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)
  • Safari West (6.6 mi / 10.6 km)
  • Old Courthouse Square (9.2 mi / 14.9 km)
  • Luther Burbank Home and Gardens (9.5 mi / 15.3 km)
  • Petrified Forest (9.6 mi / 15.5 km)
  • Armstrong Redwoods State Park (10.1 mi / 16.3 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, California, United States of America when booking a vacation rental?
When considering a vacation rental in Windsor, California, the downtown area is a fantastic choice. This vibrant neighborhood offers a charming atmosphere with easy access to several local attractions. One of the highlights is the Windsor Town Green, a picturesque park that often hosts community events and concerts, making it a lively spot for both relaxation and entertainment. Additionally, the nearby Russian River is great for outdoor enthusiasts, providing opportunities for kayaking and scenic walks along the water.

Another great area to explore is the vicinity around the wineries. Windsor is located in the heart of wine country, and many vacation rentals are situated near some of the region's best vineyards. This offers guests the chance to indulge in wine tasting and tours while enjoying the beautiful landscapes.
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, travelers should consider the nearby coastal areas of Sonoma County, particularly the charming town of Sebastopol and the scenic beaches along the Sonoma Coast State Park. While Windsor itself is inland, it offers easy access to the beautiful beaches of Bodega Bay and Jenner, where vacation rentals are plentiful and often boast picturesque ocean views.

In Bodega Bay, visitors can find beach houses equipped with amenities such as spacious decks for sunbathing, fire pits for evening gatherings, and modern kitchens for preparing fresh seafood caught locally. The area is known for its stunning coastal scenery and opportunities for outdoor activities, including kayaking and whale watching.

Jenner, located at the mouth of the Russian River, offers unique properties that often feature panoramic views of the coastline and river estuary. Many rentals here come with comfortable living spaces, outdoor dining areas, and easy access to hiking trails that lead to hidden beaches and scenic overlooks.

Additionally, the proximity to local wineries and farm-to-table dining experiences in the surrounding Sonoma County countryside enhances the appeal of renting a beach house in this region. Find your rental near the beach in Windsor.
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 19 available throughout the area. These houses often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable home base. Many also include outdoor spaces, such as patios or gardens, great for enjoying the pleasant California climate. In addition to vacation houses, there are approximately 11 condos and 11 apartments available, offering more compact accommodations for travelers seeking convenience and amenities. Villas are also present in several numbers, providing a luxurious option for those desiring more upscale stays.
Are there any family house rentals in Windsor?
In Windsor, California, there are some available family-friendly house rentals—approximately 23 options throughout the area. This charming town is surrounded by beautiful vineyards and offers a peaceful atmosphere, making it a great choice for families. Many of these homes come equipped with spacious living areas, fully stocked kitchens for family meals, and outdoor patios where children can play and adults can relax.

Visitors will also find amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a convenient stay. The local parks, such as Windsor Town Green, provide playgrounds and picnic areas, superb for family outings. Additionally, nearby attractions like the Russian River and Sonoma County's renowned wineries offer opportunities for both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Windsor?
In Windsor, California, there are plenty of vacation homes available for rent that come equipped with pools and hot tubs, with around 29 options to choose from. This charming town in Sonoma County offers a variety of residential neighborhoods where travelers can find these properties, each providing a great experience. Many rentals feature private pools, inviting hot tubs, and spacious outdoor areas superb for relaxation and entertainment. Inside, guests can expect modern amenities such as fully equipped kitchens, comfortable living spaces, and often air conditioning, ensuring a pleasant stay.
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, travelers can find a variety of pet-friendly house rentals, with around ten options available. Many of these homes come equipped with spacious backyards, allowing pets to enjoy the outdoors safely. Expect amenities such as fully equipped kitchens, comfortable living areas, and sometimes even outdoor patios or decks where guests can relax or dine al fresco.

The town is surrounded by beautiful parks and vineyards, providing ample opportunities for outdoor activities with pets. Nearby, the Windsor Town Green offers walking paths and green spaces, great for leisurely strolls with furry companions. Additionally, the region's wineries often welcome pets, allowing visitors to explore the scenic vineyards while enjoying wine tastings. See all pet-friendly rentals in Windsor.
Are there any remote work vacation rentals in Windsor?
In Windsor, California, there are numerous remote work-friendly vacation rentals available—around 38 options for travelers seeking a productive getaway. Many of these properties are equipped with reliable Wi-Fi, ensuring that guests can stay connected and work efficiently during their stay.

Travelers can expect a variety of home styles, from cozy cottages to spacious homes, often featuring dedicated workspaces or areas conducive to remote work. Amenities typically include comfortable furnishings, full kitchens for preparing meals, and outdoor spaces that provide a pleasant environment for breaks or casual meetings.

Windsor itself is a charming town located in Sonoma County, known for its beautiful parks, wineries, and proximity to the scenic Russian River. This makes it an ideal location not only for work but also for enjoying leisure activities during downtime, such as wine tasting or hiking in the nearby redwood forests. 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, vacation rentals are equipped with a variety of popular amenities that enhance the guest experience. Most properties feature a well-equipped kitchen, allowing travelers to prepare their own meals during their stay. Many rentals also come with a deck or patio, providing a lovely outdoor space for relaxation or dining al fresco. A coffee and tea maker is commonly available, ensuring guests can enjoy their morning brew at their convenience. Additionally, many rentals include a fireplace, adding a cozy touch for those cooler evenings. Onsite parking is also a standard amenity, making it easy for guests to explore the charming surroundings of Windsor and its vineyards.
When is the best time to visit Windsor for a vacation rental?
The most popular time to visit Windsor is during the vibrant months of August to October, when the region showcases its stunning fall foliage and hosts various wine-related events. This peak season attracts travelers eager to explore the picturesque vineyards and partake in delightful outdoor activities, all while enjoying the pleasant weather.

October stands out as an exceptional month to experience Windsor. With daytime temperatures typically ranging from the mid-50s to the mid-70s Fahrenheit, visitors can comfortably explore the scenic beauty of the area, partake in wine tastings, and stroll through the quaint downtown filled with charming boutiques and restaurants. The atmosphere is lively yet relaxed, making it great for those seeking a blend of adventure and leisure.

For travelers looking for a more budget-friendly option, November offers a quieter experience. While it marks the beginning of the low season, it provides an opportunity to enjoy the serene beauty of the vineyards and the crisp autumn air without the larger crowds. This can be an ideal time for peaceful walks or cozy afternoons at local wineries, where you can savor the rich flavors of the season.

Ultimately, the best time to book a vacation rental in Windsor hinges on your preferences for vibrant events and socializings or a more tranquil escape amid natural beauty.
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, California, United States of America?
In Windsor, California, visitors can explore several attractions that showcase the charm of this Sonoma County town. The Windsor Town Green is a central hub, where travelers can enjoy outdoor events, farmers' markets, and a variety of shops and restaurants nearby. This area often features vacation rentals that offer easy access to the vibrant community atmosphere.

Another highlight is the Windsor Oaks Vineyard, where wine enthusiasts can partake in tastings and tours, experiencing the local viticulture firsthand. Nearby, the Russian River provides opportunities for outdoor recreation, including kayaking, fishing, and hiking along scenic trails.

For those interested in parks, the beautiful Keiser Park offers picnic areas, walking trails, and sports facilities, making it a great spot for families and outdoor lovers alike.
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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