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Windsor vacation rentals

We found 1,065 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:Jun 12 - Jun 19

Image gallery for Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Pool
9.6 out of 10, Exceptional, (65 reviews)
Exceptional
(65 reviews)

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Healdsburg

15% off
Price is CA $1,981
CA $16,963 total
includes taxes & fees
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Find spaces that suit your style

Find out more about Windsor

Why visit Windsor

  • Charming downtown: Experience the warm hospitality of friendly locals and explore unique shops and eateries in downtown Windsor.
  • Scenic outdoor activities: Enjoy the picturesque landscapes with opportunities for hiking, biking, and relaxing by the serene river and nearby beaches.
  • Family-friendly experiences: Engage in various activities suitable for all ages, ensuring a memorable time for families visiting Windsor.
  • Romantic getaways: Discover perfect spots for couples to unwind and enjoy quality time together amidst beautiful surroundings.
  • Diverse accommodations: Choose from an array of vacation rentals, including cozy cottages and spacious homes for a comfortable stay.

Popular types of accommodation in Windsor

If you're considering a getaway to Windsor, you're in for a treat. Our vacation rentals offer a variety of popular accommodations, including houses, charming cottages, and cozy apartments. Whether you're looking to stay in a spacious Windsor house, a comfortable bedroom home, or explore options in South Windsor, we have the perfect spot for you. Enjoy your stay in Windsor with transparency and savings, ensuring a memorable experience.

  • Houses: The top choice for visitors in Windsor, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: A charming option that provides a cozy and picturesque retreat, perfect for a relaxing getaway.
  • Apartments: Convenient and modern, these rentals are great for travellers seeking a home-like atmosphere.
  • Cabins: Nestled in nature, cabins offer a rustic experience for those wanting to unwind in a serene setting.
  • Villas: Luxurious and spacious, villas are perfect for those looking to indulge during their holiday.**

Top attractions near Windsor

Windsor, California, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore picturesque sites such as piazzaSquare, the serene river, and nearby beaches. The area offers a variety of attractions that cater to those seeking cultural experiences, family-friendly activities, and beautiful scenery. Whether you're visiting with loved ones or embarking on a solo adventure, Windsor promises a memorable vacation experience.

  • Russian River: A picturesque river located 3.2km from Windsor, perfect for outdoor activities like kayaking and picnicking amidst stunning natural scenery.
  • Healdsburg Plaza: Situated 8.0km away, this vibrant square offers a cultural experience with local shops, art galleries, and restaurants, all infused with a charming city vibe.
  • Sonoma County Fairgrounds: Located 16.1km from Windsor, this family-friendly venue hosts various outdoor events and fairs, providing a fun atmosphere for all ages.

Things to do recommended for couples

Windsor offers delightful couple experiences. Visit the charming Kendall-Jackson Wine Estate and Gardens for a romantic wine tasting, or enjoy the lively atmosphere at Russian River Vineyard. For some fun, try your luck at Pee Wee Golf and Arcade, just a short drive away.

Things to do recommended for families

During your family vacation in Windsor, enjoy sweet treats at Powell's Sweet Shoppe, unwind at Spring Lake Park, just 17.7km away, or have fun ice skating at the Redwood Empire Ice Arena, located 11.3km from Windsor. It’s a perfect blend of fun and relaxation.

Things to do recommended for groups

Groups visiting Windsor can enjoy the outdoor adventure at Bohemian Grove, play a round of golf at the Healdsburg Golf Club, or experience culture and entertainment at the Raven Performing Arts Theater, all within a short distance from the town.

*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, bringing your family, taking your pets, or planning an extended stay, it's important 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'll require, along with features like a complete kitchen or outdoor space for social gatherings. Thankfully, you can easily filter for these options and much 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, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and 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 perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windsor

Windsor, California, offers a charming blend of outdoor adventures and picturesque scenery, perfect for a romantic getaway or a family-friendly vacation. Explore downtown Windsor, where friendly locals welcome you, and indulge in the natural landscapes that surround the area. With sunny weather and plenty of recreational activities, you'll find the ideal spot for relaxation and excursions. Don't miss the opportunity to discover nearby neighborhoods that enhance your travel experience in this delightful region.

  • Santa Rosa: Located 14.5km from Windsor, Santa Rosa invites visitors to explore its stunning outdoor landscapes and family-friendly activities. This vibrant city boasts scenic parks and a picturesque river, perfect for leisurely strolls or picnics. Enjoy a variety of recreational options, including golf courses and spa treatments, making it an ideal spot for relaxation. Notable attractions include event venues for conferences and access to nearby beaches, ensuring a well-rounded travel experience.
  • Healdsburg: Just 8.0km from Windsor, Healdsburg is a charming city known for its romantic ambiance and beautiful scenery. The town is a haven for outdoor enthusiasts, featuring lush parks and a lovely river that enhances its picturesque setting. Visitors can indulge in rejuvenating body treatments and unwind at local spas. The vibrant piazza square offers a delightful space for dining and shopping, while nearby beaches provide additional opportunities for relaxation and exploration.
  • Chalk Hill: A mere 3.2km from Windsor, Chalk Hill is a hidden gem for wine lovers and outdoor adventurers alike. This scenic area is renowned for its wineries, offering tastings and tours that highlight the best of Sonoma County's wine country. The beautiful river nearby adds to the charm, providing a perfect backdrop for a romantic day out. Whether you're looking to sip fine wines or enjoy the great outdoors, Chalk Hill offers a serene escape just a stone's throw from Windsor.

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

Are you hoping to save some money on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can easily create new itineraries, pick up right where you left off, or review and organize your existing plans. Any properties you've saved or booked in the past are now accessible under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • SingleThread Farm at Dry Creek (8.7 mi / 14.1 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 when booking a vacation rental?
When considering a vacation rental in Windsor, California, the charming neighbourhood of Downtown Windsor is an excellent choice. This area boasts a variety of properties, from cosy cottages to spacious family homes, suiting different preferences and budgets. Staying here places you within walking distance of delightful local attractions, such as the Windsor Town Green, a lovely park featuring a pond, picnic areas, and a vibrant community atmosphere. Additionally, the nearby Russian River offers opportunities for outdoor activities like kayaking and cycling, making it a fantastic spot for nature enthusiasts.

Another appealing area is the nearby Windsor Golf Club, which not only provides stunning views but also easy access to the picturesque Sonoma County wine country. This region is renowned for its award-winning wineries and vineyards, great for those looking to explore local wine tasting experiences.
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 travelling 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.
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.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, vacation houses are the most popular type of vacation rental, with around 76 available in the area. These homes typically provide spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort during their stay. Many also feature outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring the surroundings. Condominiums and apartments are also common, with approximately 44 of each type, appealing to those looking for a more compact option without sacrificing amenities.
Are there any family house rentals in Windsor?
In Windsor, California, there are some family-friendly house rentals available, with approximately 23 options to choose from. This charming town is located in Sonoma County, renowned for its picturesque vineyards and proximity to various outdoor activities. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor spaces ideal for family gatherings or barbecues.

Guests can enjoy amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The locale is close to scenic parks like Windsor Town Green, which offers playgrounds and open spaces for children to explore. Additionally, the nearby Russian River provides opportunities for kayaking and picnicking, making Windsor an excellent choice for families seeking a blend of 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 feature pools and hot tubs, with around 29 options to choose from. This charming town, located in Sonoma County, offers a serene atmosphere surrounded by beautiful vineyards and picturesque landscapes. Many of these properties include amenities such as private swimming pools, relaxing hot tubs, and spacious outdoor areas superb for entertaining or family gatherings.

Travellers can also expect fully equipped kitchens, comfortable living spaces, and some rentals may offer additional features like barbecue facilities and fire pits, enhancing the experience of enjoying the warm Californian weather.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windsor?
In Windsor, there are several pet-friendly house rentals available for travellers seeking a comfortable stay. Many of these properties typically feature spacious layouts, fully equipped kitchens, and outdoor areas such as gardens or patios, allowing pets to roam freely. The homes are often designed with amenities like laundry facilities, Wi-Fi, and inviting living spaces to ensure a pleasant experience for guests.

The neighbourhood itself is family-friendly and offers a variety of parks where pets can enjoy the outdoors. The nearby Windsor Town Green is a lovely spot, featuring walking paths and open spaces ideal for leisurely strolls with pets. Additionally, the surrounding Sonoma County area is known for its scenic vineyards and wineries, many of which are pet-friendly, providing opportunities for wine tasting while enjoying the company of your furry friends.
Are there any remote work vacation rentals in Windsor?
In Windsor, California, there are numerous options for remote work vacation rentals, with around 152 available throughout the area. This charming town offers a blend of natural beauty and modern conveniences, making it an ideal spot for those looking to work remotely. Many properties feature essential amenities such as free Wi-Fi, ensuring you stay connected during your work hours.

Travellers can expect a variety of accommodations, including spacious homes with dedicated workspaces, comfortable living areas, and fully equipped kitchens, allowing for a productive and enjoyable stay. The surrounding regional parks and the scenic Russian River provide opportunities for leisure activities after work, with options for hiking, biking, and exploring the local vineyards. 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 travellers 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 rentals typically feature a range of amenities to enhance the stay experience. Most properties come equipped with kitchens, allowing guests to prepare their own meals and enjoy the convenience of home cooking. Many rentals also include outdoor decks or patios, great for relaxing and enjoying the pleasant California weather. Additionally, a coffee and tea maker is commonly provided, suiting those who appreciate a warm beverage at any time. For added comfort, many accommodations have fireplaces, creating a cosy atmosphere, especially during cooler evenings. Onsite parking is also a common amenity, making it convenient for guests with vehicles.
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 charming town in California is a prime destination for wine enthusiasts and outdoor adventurers alike, as the vineyards are bursting with activity during the harvest season. The warm, sunny days, typically ranging from 15 to 25 degrees Celsius, create an inclusive setting for exploring the beautiful wineries and enjoying outdoor activities.

October offers a unique opportunity to experience the vibrant autumn colours in the surrounding landscapes, making it a superb time for leisurely walks or bike rides through the scenic vineyards. The pleasant weather also allows for al fresco dining at local restaurants, where you can savour delicious farm-to-table cuisine paired with exquisite local wines.

For those who are looking to travel on a budget, consider planning your visit in November. While this month falls outside the bustling tourist season, it still holds its own charm, featuring a peaceful ambiance and the chance to enjoy the last remnants of autumn while avoiding large crowds.
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, California, visitors can explore a variety of attractions that highlight the area's natural beauty and local culture. The Windsor Town Green is a central hub featuring a scenic park, walking paths, and a variety of events throughout the year, making it a lovely spot for relaxation and community gatherings. Nearby, the Russian River offers opportunities for kayaking, fishing, and picnicking along its banks, appealing to outdoor enthusiasts.

Wine lovers will appreciate the proximity to the renowned Sonoma County wine region, with several vineyards and tasting rooms just a short drive away. The nearby Oliver's Market is a great place for local produce and gourmet foods, adding to the culinary experience of the area.

For those seeking a bit of adventure, the nearby Foothill Regional Park offers hiking trails, picnic areas, and beautiful views, great for a day out in nature. Additionally, the historic Windsor Historical Society provides insights into the town's past and showcases local heritage.
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 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 travellers 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 cosy cabin or a beach house, 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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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