Discover a selection of 1,000 vacation rentals in Windsor, CA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $167 per night, and houses and cabins are popular options for a stay in Windsor. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Windsor
Destination guide

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.

Things to do

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:

  • Matrix Winery (3.7 mi / 6 km)
  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Russian River Vineyard (6.7 mi / 10.8 km)
  • Mazzocco Winery (8.8 mi / 14.1 km)
  • Dry Creek Vineyard (9.4 mi / 15.1 km)
  • Marimar Estate Vineyard (9.8 mi / 15.7 km)
Natural features

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)
  • Petrified Forest (9.6 mi / 15.5 km)
  • Armstrong Redwoods State Park (10.1 mi / 16.3 km)
How to get there

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.

What are the top vacation rentals in or near Windsor?

The heart wants what the heart wants, and right now that's a vacation. Now's the time to pack your bags and head for one of these top vacation rentals in or near Windsor:

  • Make the most of amenities including a blender and a private pool at "Brambleberry - Idyllic And Private Estate". Situated around 16 miles from Windsor, this vacation rental has 3 bedrooms and is a hit with guests.
  • "A Stylish Getaway In The Heart Of Sonoma Wine Country" is another top-notch choice, offering 3 bedrooms, a garage, spa and beauty services and more. It's around 17 miles from Windsor.

For even more great options, use the search bar at the top of the page to find the perfect Windsor vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Windsor?

At Vrbo, we think weekends were made for having fun. Escape to one of these weekend getaways in and near Windsor and experience all the terrific things to do close by:

  • Located 20 miles to the southwest of the center of Windsor, "Views New Hot Tub; Across From Beach Path" is popular among nature lovers and adventure seekers. Stay busy by exploring nearby outdoor attractions, including Lake Sonoma and Sonoma County Museum. Then, take the opportunity to try cycling or fishing.
  • Alternatively, enjoy a slower pace of life at "Stunning Tuscan House In The Heart Of Sonoma's Wine Country". About 19 miles southeast of Windsor, fun activities around here include mountain biking and golf. Prefer sightseeing? Make a beeline for Armstrong Redwoods State Park and Sepay Groves Olive Oil and Vinegars.

Can I find studio apartments for rent in and around Windsor?

Typically compact, reasonably priced and conveniently located, it's not difficult to be impressed by a studio apartment. Make yourself comfortable in one of these vacation rentals and experience the energy of Windsor up close:

  • Explore the world around you from the comfort of "Stunning Tuscan House In The Heart Of Sonoma's Wine Country". This vacation rental is a popular base for discovering the sights and offers amenities including shopping and an ice maker.
  • Another appealing choice is "The Perfect Wine County Couples Retreat". Take advantage of heating, an oven and other amenities during your vacation.

When you're ready to step out of your studio apartment and do some exploring, there's loads to keep you busy around Windsor. Enjoy cultural attractions? Visit Luther Burbank Center for the Arts and Petaluma Arts Center.

Can I find short term rentals in or near Windsor?

From time to time, you just need to take a break from it all, even if it's only for a few short days. Experience a nice mix of exploring and relaxing at one of these short-term rentals in or around Windsor:

  • "Snowbirds Winter 2023 Available" is close to the heart of Windsor, which means there are loads of things to do and see. Explore top attractions like Bohemian Grove and Russian River Vineyard when you're not making the most of your cozy property.
  • Sleep, eat and explore your surroundings from "The Perfect Wine County Couples Retreat", another good option. Korbel Champagne Cellars and Armstrong Redwoods State Park should be on your to-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Windsor?

Whether spent in a luxury condo or a rustic cabin, a romantic weekend getaway is a fantastic way to add some zing to your relationship. Whisk your sweetheart off for a couple of leisurely days at one of these enticing escapes in or near Windsor:

  • Sneak away on Friday afternoon for a few passion-filled nights at "Brambleberry - Idyllic And Private Estate". Roughly 16 miles from Windsor, this place comes with lots of nice touches, like beauty services and winery tours.
  • Otherwise, spend a few blissful days sipping wine and canoodling at "A Stylish Getaway In The Heart Of Sonoma Wine Country", around 17 miles from Windsor. Winery tours and a fireplace will help set the mood for romance.

Are there mansions for rent in or near Windsor?

Nothing screams "Best. Vacation. Evvv-er." like staying in a mansion. Treat your loved ones to a truly unforgettable escape at one of these mansions for rent in and around Windsor:

  • Approximately 9 miles to the southeast of Windsor is "Luxury Historic Mansion: 9 Bedrooms". Along with its awe-inspiring design, you'll also love its top-notch amenities, such as a swimming pool and beauty services.
  • With a swimming pool, ski lift privileges and loads of other awesome amenities, "Belleza By Avantstay | Hilltop Mansion W" will get your squad's nod of approval. This sumptuous retreat is roughly 20 miles to the southeast of Windsor.

What are the best large group vacation rentals in or near Windsor?

Vacation with others and have twice as much fun. Whether you're planning an adventurous escape with friends for a family get-together, you'll have your choice of large group vacation rentals in and around Windsor:

  • Providing privacy, comfort and space, you'll get everyone's stamp of approval at "5 Bedroom 6 1/2 Bath Luxury Home On 3+ Acres". Up to 12 people can be accommodated at this retreat which has 5 bedrooms, a swimming pool and a garden. You'll discover it around 6 miles to the northwest of Windsor.
  • "Luxury Golf Course Home With Spectacular Ocean Views 'royal Pacific" is another excellent option. It's around 20 miles to the southwest of Windsor, has 5 bedrooms and sleeps up to 12 guests. A beach view and a chef are among the things designed to make your stay even more comfortable.

What are the best houses for rent with a pool in or near Windsor?

Of all the conveniences a vacation rental can offer, a pool is easily the most fun. Have a look at these houses for rent with a pool in or near Windsor and spend your days splashing about. Just remember to bring your flamingo floatie:

  • Switch to vacay mode at "Stunning Tuscan House In The Heart Of Sonoma's Wine Country", where your biggest priority will be pool time. Amenities such as a microwave oven and a living room help make this escape a favorite with guests.
  • "Sapphire Canyon Vineyard Guest House" is the sort of place you go to get away from the everyday and make the most of your surroundings, starting with its inviting pool. A microwave oven and outdoor furniture are also on hand to make your stay nice and comfortable.

Curious what the weather is like in Windsor? It has a mediterranean climate, with average temperatures in summer ranging from 55 ºF to 80 ºF. If you'd like more inspiration on where to stay in this popular destination, use the search bar at the top of the page and adjust the filters to check out our entire range of Windsor vacation rentals.

What are the best large family vacation rentals in or near Windsor?

It's always more fun when you share precious moments with the folks closest to your heart. Whether you're organizing a family catch-up or spending time with friends, we'll have a large vacation rental that's just right for you. These are two of our best in and around Windsor:

  • Get your group under the same roof at "Brambleberry - Idyllic And Private Estate", which has 3 bedrooms that sleep up to 8 guests. This escape is around 16 miles to the southeast of Windsor and features amenities such as towels and a TV.
  • Another great choice is "A Stylish Getaway In The Heart Of Sonoma Wine Country". This property is 17 miles southeast of Windsor and comes with a toaster, a smart TV and more. With 3 bedrooms accommodating up to 8 people, you won't have to leave anyone off your invitation list.

If you want to see some family-friendly attractions in the area, you have plenty of choice. Safari West, Sonoma County Fairgrounds and Sonoma TrainTown Railroad offer fun for young and old.

Can I find family cabin rentals in or near Windsor?

Cozy up with your kiddos in a family cabin rental in or near Windsor and get ready to build some incredible new memories together. Check out these favorites:

  • "Rustic Cabin In Dry Creek Valley With Beautiful Views" - Around 8 miles northwest of central Windsor, this family-friendly retreat comes with a microwave oven and coffee and tea making facilities.
  • "Mckinney Cabin Salmon Creek - Spectacular Coastal Views" - This property is also ideal for families and is around 19 miles southwest of Windsor. Offering coffee and tea making facilities, childrens activities and more, it'll get your group's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Windsor vacation rental that's perfect for your needs.