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. 

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
Herb Retreat
4 Bedroom | 3.5 Bath | Sleeps 8

Herb Retreat - Windsor, CA

$595 avg / night
Red Rooster Cottage
1 Bedroom | 1 Bath | Sleeps 4

Red Rooster Cottage - Windsor, CA

$160 avg / night
Wine Country Getaway
3 Bedroom | 2 Bath | Sleeps 6

Wine Country Getaway - Windsor, CA

$99 avg / night
Summer Oasis
3 Bedroom | 2.5 Bath | Sleeps 8

Summer Oasis - Windsor, CA

$375 avg / night
Wine County Retreat
3 Bedroom | 3 Bath | Sleeps 8

Wine County Retreat - Windsor, CA

$503 avg / night

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Recent Windsor vacation rental reviews

A delightful house to rest and relax in between enjoying the wonders of Windsor.
Nancie M. | Apr 2024
Clean, comfortable, and close to stores and restaurants! Will be back.
Travis A. | Apr 2024
The home was easy to find. I liked the frequent and timely communication via text and email from Vacasa. The back patio was quite lovely. Unfortunately, it was rainy when we arrived so, we only admired it from inside. The decor and fine. Couches were not super comfy. Even though the house had a Keurig, we were disappointed no coffee had been supplied. The main challenge we had with the property was that the code provided for the front door lock would not work. We arrived after 9:30 pm in the pouring rain so, this was a very frustrating situation. I tried calling the 800 number 3x before I reached a human being. Thankfully, we were able to reach the property manager by ringing the Ring camera. She was able to direct us to the spare key. Grateful she was able to help but, I don't know what we would have done if we hadn't been able to reach her. The next day, she installed a new lock for the door. We didn't have any issues with the code this time. Changing out the whole lock seemed a bit extra to me. Why not just give us a new code? Perhaps, there were issues with the lock for other customers but, the support person I spoke with said no issues were reported. My final critique is no specific instructions for checking out were provided by Vacasa nor in the folder with info from the property manager. Most Airbnb/VRBO places give instructions such as, "run the dishwasher before you leave, put all dirty towels in the laundry room, empty the trash cans," etc...We did these things regardless but, more specific instructions would have been good so as to make sure we wouldn't be charged any additional cleaning fees. Anyways, while we didn't spend much time at the home, overall, we were comfortable and grateful that we were able to have the lock situation delt with.
Johanna R. | Apr 2024
Windsor vacation rental FAQ

Yes, 45 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. 84 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.