Windsor Vacation Rentals

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USA > California > Windsor

Make Windsor your next getaway—choose from 10 great vacation rentals

Escape to scenes of gently rolling mountains, world-famous wines, and a touch of idyllic luxury. Our Windsor vacation rentals are the place to get away from it all—and to enjoy a glass of pinot or two. 

Explore Windsor house rentals, cottages, and more

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House rentals

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Cottages

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Windsor vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Wine County Retreat
3 Bedroom | 3 Bath | Sleeps 8

Wine County Retreat - Windsor, CA

$703 avg / night
Red Rooster Cottage
1 Bedroom | 1 Bath | Sleeps 4

Red Rooster Cottage - Windsor, CA

$224 avg / night
Wine Central
4 Bedroom | 3 Bath | Sleeps 10

Wine Central - Windsor, CA

$877 avg / night
Wine Country Hideaway
3 Bedroom | 2 Bath | Sleeps 6

Wine Country Hideaway - Windsor, CA

$362 avg / night
Wine Country Hideaway
3 Bedroom | 2 Bath | Sleeps 6

Wine Country Hideaway - Windsor, CA

$337 avg / night

View 5 more homes

Recent Windsor vacation rental reviews

We took a couple of days to go wine tasting and golfing. The house was in a good location, clean and updated. The kitchen was well appointed for preparing our meals. The hot tub was a nice treat after a full day of golf.
Amanda R. | Dec 2022
We liked the roominess of all the rooms and modern appointments, the quiet neighborhood and many family members loved the large spa. We stayed in the dead of winter and think fall or summer might be awesome. The kitchen is mostly well-equipped, beds comfy.
Judy B. | Dec 2022
We loved our Stay at Lord Manor, it was so spacious, the backyard was quiet and relaxing to hang out in, just minutes walk to downtown restaurants, pubs and the Town Green. Each room had a fun theme and my son loved the Jungle Room as well as the largeness of the Master Suite and the Tub was a hit. I would stay in this home again and again as it is central to northern redwoods, south to the city, west to the Ocean and Bodega Bay, and east to Sonoma & Calistoga. Perfect location. and super inviting comfortable home to be in.
Melissa R. | Nov 2022
Windsor vacation rental FAQ

Yes, 22 of our Windsor homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 52 of our Windsor vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Windsor vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Windsor team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Windsor, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Windsor, CA?

You’ll find this charming town tucked in the foothills of the Mayacamas Mountains, just nine miles north of Santa Rosa. Windsor sits in Sonoma County, an area known for its stellar wines—in fact, there are at least 425 wineries located here. The town is only 63 miles north of San Francisco, and perfect for a weekend getaway. Between the stunning landscape of the Russian River Valley and nearby redwood forests, our Windsor cottage rentals are truly surrounded by unforgettable beauty.

Things to do near our Windsor vacation rentals

Of course, one of the most alluring things about Sonoma County is the wine scene. In the town of Windsor alone, you can find a number of wineries, vineyards, and tasting rooms. Play croquet amid the beautiful landscape of Sonoma-Cutrer Vineyards, visit Martinelli Vineyards’ tasting room in a beautiful renovated barn, or enjoy a picnic lunch with your vino at the lesser-known Russian Hill Vineyards.

Don’t be fooled by the near-endless opportunities to indulge in local wine: Windsor is a great family-friendly destination, too. Its downtown area is perfectly strollable and there are several local parks where the kids can roam free. In the summers, you can even enjoy live music performances or outdoor movie screenings. For a truly unforgettable experience, take in the beautiful landscape from a bird’s eye view with a private hot air balloon ride. 

For those heading to a Windsor vacation rental to sample the outdoors, you won’t be disappointed. Foothill Regional Park provides 211 acres of trails that are perfect for biking, hiking, and even horseback riding. If you’ve worked up an appetite, there’s no shortage of dining options. Enjoy a hearty breakfast in a retro diner at KC’s American Kitchen, indulge in sushi at Umé Japanese Bistro, or visit the Jaded Toad for some barbecue and a sunny beer garden.

There’s so much to love about beautiful Sonoma County. Come experience the best of it with a Windsor vacation rental. Browse our collection of homes today and pick your next California retreat.