Photo by Jennifer Hill

Windsor vacation rentals

We found 1,052 vacation rentals — enter your dates for availability

Select from 43 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:Aug 1 - Aug 8

Image gallery for Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Pool
10 out of 10 rating
Exceptional
(19 reviews)

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Santa Rosa, CA

9% off
Price is $1,527
per night
$10,691 total
All fees included
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Find spaces that suit your style

  • 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

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)
  • Rubicon Adventures (8.5 mi / 13.6 km)
  • Korbel Winery (8.5 mi / 13.7 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.

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