Photo by Jennifer Hill

Windsor vacation rentals

We found 1,048 vacation rentals — enter your dates for availability

Select from 40 houses, 31 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:Oct 10 - Oct 17
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Windsor

Why visit Windsor

  1. Outdoor Adventures: Windsor is ideal for outdoor enthusiasts, offering scenic parks and trails perfect for hiking and biking.
  2. Charming Neighborhoods: Explore beautiful residential areas filled with friendly locals and picturesque homes.
  3. Cultural Attractions: Visit local landmarks like piazzaSquare and fairgroundShowGround for a taste of Windsor's vibrant culture.
  4. Scenic River Views: Enjoy leisurely excursions along the scenic river, perfect for romantic strolls or family outings.
  5. Cozy Vacation Rentals: Find the perfect home away from home with a variety of charming vacation rentals to choose from.

Popular types of accommodation in Windsor

Planning a getaway to Windsor? Discover the perfect home away from home with our selection of vacation rentals. From charming houses and cozy cottages to rustic cabins, there’s something for everyone. Whether you’re traveling with family or seeking a serene retreat, Windsor vacation rentals offer comfort, convenience, and the ideal base for your adventures. Start your journey today and find the perfect family rental to create unforgettable memories!

  • Houses: The top choice for visitors in Windsor, offering spacious and comfortable settings for families or groups.
  • Cottages: A charming option for those seeking a cozy and intimate atmosphere amidst scenic surroundings.
  • Cabins: Perfect for nature lovers, these rustic retreats provide a peaceful escape with a touch of adventure.
  • Apartments: Ideal for solo travelers or couples, offering convenient amenities in a home-like environment.
  • Villas: Luxurious accommodations that provide a touch of elegance and comfort for a memorable stay.**

Top attractions near Windsor

Windsor, California, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore charming spots like piazzaSquare, fairgroundShowGround, and the scenic river. The area's attractions offer a blend of culture, nature, and urban experiences, making it an ideal destination for travelers looking to immerse themselves in local charm and beauty.

  1. Russian River: Located 2 miles from Windsor, the Russian River offers breathtaking scenery and outdoor activities. Enjoy kayaking, fishing, or simply relaxing by the riverbank while soaking in the natural beauty of the area.
  2. Healdsburg Plaza: Just 5 miles away, Healdsburg Plaza is a vibrant public square rich in culture. Stroll through art galleries, boutique shops, and enjoy local cuisine at nearby restaurants, all while experiencing the lively community atmosphere.
  3. Charles M. Schulz Museum: Situated 7 miles from Windsor, this charming museum celebrates the beloved cartoonist of "Peanuts." Explore exhibits showcasing Schulz's work, creativity, and the impact of his characters on popular culture.

Things to do recommended for couples

For a romantic getaway in Windsor, explore the stunning Kendall-Jackson Wine Estate and Gardens, just 4 miles away, for wine and romance. Consider an adventurous day at Rubicon Adventures, 8 miles away, or enjoy some fun at Pee Wee Golf and Arcade, located 10 miles from Windsor.

Things to do recommended for families

Families visiting Windsor, California, can indulge in sweet treats at Powell's Sweet Shoppe, unwind at Spring Lake Park, only 11 miles away, or enjoy ice skating at the Redwood Empire Ice Arena, located 7 miles from town. Each venue offers a fun, family-friendly atmosphere!

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

When traveling with a group, family, pets, or planning extended stays, it's important to prioritize your preferences. Here are some helpful tips for booking on Vrbo.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, along with amenities like a full kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private 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 families, a getaway isn't truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're in search of vacation rentals offering discounts for month-long stays, 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 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 perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot for families and couples alike. Explore the charming residential neighborhoods, filled with beautiful homes and friendly people. Nearby regions boast sweeping views and a relaxing atmosphere, perfect for leisurely excursions. Enjoy the sunny weather while discovering the vibrant local culture and recreational activities that Windsor has to offer.

  • Santa Rosa: Located 9 miles from Windsor, Santa Rosa is a vibrant city known for its outdoor adventures and family-friendly atmosphere. Visitors can enjoy a range of activities, including rejuvenating body treatments and rounds of golf at well-maintained courses. The city boasts scenic views along the river and offers venues for events and conferences, making it a versatile destination. Whether you're looking to relax on the beach or explore the local parks, Santa Rosa provides an enriching travel experience with something for everyone.
  • Healdsburg: Just 5 miles from Windsor, Healdsburg is a charming city that combines outdoor beauty with romantic vibes. This picturesque town is perfect for couples and nature enthusiasts alike, offering a variety of activities such as spa treatments and leisurely strolls through recreational areas. The local attractions include a scenic river and a quaint piazza square, where visitors can enjoy local shops and restaurants. Healdsburg's enchanting atmosphere and stunning landscapes make it a perfect spot for a relaxing getaway.
  • Chalk Hill: Situated only 2 miles from Windsor, Chalk Hill is a hidden gem for those seeking outdoor entertainment and breathtaking scenery. This area is renowned for its wineries, making it an ideal destination for wine lovers. Visitors can indulge in wine tastings while enjoying the stunning views of the surrounding landscape. The scenic river adds to the charm of Chalk Hill, providing a serene backdrop for a day of exploration and relaxation in this beautiful part of California.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 a breeze

Are you hoping to cut costs on your upcoming trip? One effective strategy is to stay flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To help you find the perfect Vrbo property that fits your budget, utilize our filters to sort 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 your entire booking. Being the planner certainly has its perks! When you join our travel rewards program, OneKey, you'll gain access to exclusive discounts and accumulate OneKeyCash™ on eligible bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your next adventures. You can effortlessly create new trips, resume planning from where you last stopped, or manage your travel plans all in one place. Your saved or booked properties will be organized into categories such as Potential, Upcoming, or Current Trips. To begin 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:

  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Russian River Vineyard (6.7 mi / 10.8 km)
  • Wilson Winery (7.8 mi / 12.6 km)
  • Rubicon Adventures (8.5 mi / 13.6 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 most popular type of vacation rental accommodation in Windsor?
According to our research, condos are considered the most popular type of vacation rental in Windsor. But of course, everyone's idea of the perfect stay isn't going to be the same. Vrbo has vacation rentals of all shapes and sizes, and we'll help you find the perfect fit for you.
How much does it cost to rent a vacation rental in Windsor?
The average price for a vacation rental in Windsor can vary based on factors including time of year, length of stay and property type. Whether you're searching for a villa with space for extended family or a quaint cottage for just you and your sweetheart, just add your travel dates to discover stays with exceptional value.
How much does it cost to rent a beach house in Windsor?
When you travel and the style and size of the property will influence the cost of your beachside stay. Enter your Windsor travel dates to see your options on Vrbo. Can't live without a private pool? Use our filters to choose the features and amenities you need.
Are there pet-friendly vacation rentals in Windsor?
You're in luck! There are. You'll have your pick of 161 vacation rentals that cater to pets in Windsor. Plenty of our pet-friendly vacation rentals come with a garden for your furry pal to play in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Windsor?
Add a whole other level of fun to your adventure by staying in one of the 105 houses with a private pool in Windsor. Use our search filter to find the kind of property you want on Vrbo, and then spend leisurely days playing and splashing in a swimming pool that's all your own.
What are popular rental amenities in Windsor?
When it comes to rental amenities that people are on the lookout for in Windsor, a barbecue grill, a fireplace and a chef rank highest. With Vrbo vacation rentals, you'll discover options to match your taste and style, whether you're planning to get away with your partner, your family or even pets.
Are there large group vacation rentals in Windsor?
Take your pick of 21 vacation homes in Windsor that can host a group of 10 or more people. Whether you're planning time away with the family or a special event like a birthday party, there's ample room to get your loved ones together under the same roof.
Are there vacation rentals in Windsor that welcome kids?
Windsor has 159 family-friendly vacation rentals. And booking a stay that welcomes children is easy with Vrbo's "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get amenities and perks like living rooms, yards and private pools.
What are the top attractions for families in Windsor?
Keeping the kids occupied during your vacation in Windsor is a breeze with these top family-friendly attractions:

  • Pacific Coast Air Museum
  • Windsor Golf Club
  • Powell's Sweet Shoppe - Windsor

Are there one-bedroom vacation rentals in Windsor?
You can choose from 20 one-bedroom rentals in Windsor. Whether you'd like a secluded cottage or a condo, our one-bedroom properties are great if you don't require lots of room. One of the best parts about having your own digs? You'll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Windsor?
Windsor has 46 two-bedroom properties for you to pick from. Enjoy a vacation home with all the privacy and space you want at a price that's hard to resist on Vrbo.
Are there vacation rentals with WiFi in Windsor?
You can choose from 45 vacation rentals with WiFi in Windsor. If you'd like to disconnect from the world during your break, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Windsor?
Pick your travel dates and then make use of our filters to find vacation rentals with ac in Windsor on Vrbo. With 148 air-conditioned properties available, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a vacation rental in Windsor?
We advise checking with the Windsor vacation property you'd like on Vrbo as the minimum age varies. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Windsor for?
The amount of time you can book a Windsor vacation home for depends on the property. Just put in your travel dates to see options that offer long-term stays. They feature everything you need to make your extended break more enjoyable and convenient, such as kitchens and yards. Some properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Windsor?
In Windsor, you'll find some great discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're wanting a mini vacay or a few weeks away, we've got a host of options that'll suit your style.

More Vacation Rentals ideas

People also search for