Photo by Jennifer Hill

Windsor holiday rentals

We found 1,043 holiday rentals — enter your dates for availability

Select from 41 houses, 31 flats and other holiday rentals to find the perfect place for your stay in Windsor. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting friendly Windsor

The area's wineries and festivals are just some of the reasons to come on holiday to Windsor. This welcoming city is known for its restaurants, bird watching and hiking. With a holiday 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

Do you want to discover things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windsor a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Dry Creek Vineyard (9.4 mi / 15.1 km)

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling 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 centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Windsor?
Resorts are the most popular style of holiday home in Windsor, according to our data. Even if you’ve got a different vision in mind, Stayz has holiday homes in many shapes and sizes. Browse our options to find your perfect match.
How much does it cost to rent a holiday home in Windsor?
Property type, length of stay and season are some of the conditions that can determine the price of a holiday home. Simply enter your travel dates to find your ideal match. From quaint country cottages to plush villas, all Stayz holiday homes offer amazing 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 how much you’ll pay for your beachside stay. Put in your Windsor travel dates to view your available options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the amenities and features you want.
Are there pet-friendly holiday homes in Windsor?
Pack a squeezy toy and a bone for your pup because Windsor has 123 holiday homes that roll out the welcome mat to pets. Let your four-legged friend enjoy the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Windsor?
Dig out your swimwear and swim ring, because there are 91 houses with a private pool in Windsor. Book a stay at one of these sought-after holiday homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the “pool” filter to find a place to make a splash!
What are popular home amenities in Windsor?
When it comes to home amenities that people look for in Windsor, tennis, a garden and a firepit rank highest. With Stayz holiday homes, you’ll find options to match your taste and style, whether you’re on a trip with family members, friends or even pets.
Are there large group holiday homes in Windsor?
Windsor has six holiday homes that can accommodate 10 or more people. These stays come with enough space to share good times with family and friends.
Are there holiday homes in Windsor that welcome kids?
Gather the whole crew for a memorable adventure in Windsor at one of our 123 family-friendly holiday properties. Lots of these stays come with amenities that are ideally suited to trips with youngsters, like laundry facilities, multiple bedrooms and pools. Just click on the “Properties good for families” filter and choose your favourite.
What are the top attractions for families in Windsor?
Keep your kids occupied at these popular family-friendly attractions in Windsor:

  • Safari West
  • Rubicon Adventures
  • Sonoma County Museum

Are there one-bedroom holiday homes in Windsor?
Yes, you’ll find 16 one-bedroom properties in Windsor to pick from. A one-bedroom holiday property is an excellent option if it’s just two of you or if you’re holidaying solo. Add in more privacy, space and convenience than a hotel, and you’re sure to have a getaway to remember.
Can I find two-bedroom holiday homes in Windsor?
Pick from 43 two-bedroom homes in Windsor. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There’s enough space for whoever’s fortunate enough to be joining in on the fun.
Are there holiday homes with WiFi in Windsor?
You’ll have a choice of 26 holiday homes with WiFi in Windsor. If you want to disconnect from the world while on holiday, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Windsor?
Windsor has 114 holiday homes where you can wind down in air-conditioned comfort. To locate a property on Stayz that offers this perk, enter your desired travel dates and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Windsor?
The minimum age is normally 16, 18 or 21. It can vary from one property to another on Stayz, so look at the rules of your chosen Windsor holiday home before booking.
How long can I rent a holiday home in Windsor for?
It’s up to the Windsor property. To browse available options offering extended stays, just enter your travel dates and number of guests into the Stayz search page. Look forward to having the place to yourself, along with home comforts like a fully-equipped kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

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