Windsor Vacation Rentals

Compare 7 vacation rentals.
USA > California > Windsor

Make Windsor your next getaway

Come experience the beauty of Sonoma County with a Windsor vacation rental. Escape to scenes of gently rolling mountains, world-famous wines, and a touch of idyllic luxury. You’ve found the perfect spot to get away from it all—and to enjoy a glass of pinot or two. 

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House rentals

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Windsor vacation rentals for every getaway

Dog-friendly Hot tub Internet
Herb Retreat
4 Bed | 3.5 Bath | Sleeps 8

Herb Retreat - Windsor, CA

$892 avg / night (excludes fees and taxes)
Red Rooster Cottage
1 Bed | 1 Bath | Sleeps 4

Red Rooster Cottage - Windsor, CA

$239 avg / night (excludes fees and taxes)
Wine Country Getaway
3 Bed | 2 Bath | Sleeps 6

Wine Country Getaway - Windsor, CA

$245 avg / night (excludes fees and taxes)
Summer Oasis
3 Bed | 2.5 Bath | Sleeps 8

Summer Oasis - Windsor, CA

$549 avg / night (excludes fees and taxes)
Wine County Retreat
3 Bed | 3 Bath | Sleeps 8

Wine County Retreat - Windsor, CA

$754 avg / night (excludes fees and taxes)

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Recent Windsor vacation rental reviews

Beautiful house! The swimming pool and fire pit were a hit with our group. Loved the office space upstairs. Can’t wait to stay here again.
Yvette H. | Jun 2024
What a great place to stay, has everything you could want or need. Beautiful house!
Angelo B. | Jun 2024
This home is well equipped for 6 guest with plenty of room. Breezy outdoor patio and garden area to chill out for that last glass of wine.
Richard G. | May 2024
Windsor Frequently Asked Questions

Yes, 46 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. 85 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

Explore our Windsor, CA, vacation rentals

For those heading to a Windsor vacation rental to sample the wine or the outdoors, you won’t be disappointed. 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. Foothill Regional Park boasts 211 beautiful acres to explore and during the summer, you’ll find ample live music performances or outdoor movie screenings. 

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 beautifully renovated barn, or enjoy a picnic lunch with your vino at the lesser-known Russian Hill Vineyards.

For a truly unforgettable experience, take in the beautiful landscape from a bird’s eye view with a private hot air balloon ride. 

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.