Photo by Jennifer Hill

Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (1135)
"Close to main stores, freeway and good restaurants "
The price is €135
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Windsor Wine Country, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (749)
"Simplemente ideal en todo sentido… 10/10"
The price is €126
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Windsor Wine Country, an IHG Hotel

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1037)
"Property was very nice. Brian at the front desk was excellent. I stayed in an accessible studio beautiful spacious. Only thing I saw that needed to be fixed was inside the bathroom on the walls. Either mold mildew something towards the ceiling. "
The price is €139
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Windsor - Sonoma Wine Country

WorldMark Windsor

3.0 star property
9.0 out of 10, Wonderful, (290)
"Stay was great! Place was quiet and the rooms were spacious and clean. great value for anyone who plans on coming into Windsor! Clubhouse had family and kid activities and there's a restaurant adjacent to the property. Staff was professional and friendly. Shout out to Aldo, Caleb, Domin and Jennifer! "
WorldMark Windsor

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

9.6 out of 10, Exceptional, (178)
"The house was perfect for our family getaway weekend! Very comfortable and convenient to everything!"
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Charming farmhouse amongst the vines

8.0 out of 10, Very good, (1)
"Lovely location. Beautiful yard. Wish we would have had more time to spend in the outdoor areas Plenty of room for the 6 of us. Few minor issues (nothing that affected our stay) with the home. Owners said they'd come the next day, but never did. We likely would stay there again if in the area."
Charming farmhouse amongst the vines

Gorgeous Resort in California Wine Country, Windsor!

9.4 out of 10, Exceptional, (3)
"We were three couples visiting the wine region. The condo is very clean and beds are very comfortable. The large kitchen was perfect for preparing breakfast and meals. The resort itself is also well maintained we enjoyed relaxing in the pool and the hot tub. "
Gorgeous Resort in California Wine Country, Windsor!

Gorgeous Resort in California Wine Country, Windsor!

Gorgeous Resort in California Wine Country, Windsor!

Gorgeous Resort in California Wine Country, Windsor!

Gorgeous Resort in California Wine Country, Windsor!

Private Vineyard Residence - 10 minutes from Healdsburg

10.0 out of 10, Exceptional, (1)
"My family had a wonderful, relaxing stay! The house is nicely renovated with a great kitchen, comfortable beds, and a lovely deck that wraps around the house with views of adjacent wineries. We really appreciated the opportunity to enjoy the wine and food at Bricoleur. Deacon was the best host! He met us on the days that we checked in and out, and was very responsive via text. Would love to stay again!"
Private Vineyard Residence - 10 minutes from Healdsburg

Gorgeous Resort in California Wine Country, Windsor!

Gorgeous Resort in California Wine Country, Windsor!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Windsor you may be interested in

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (1135)
"Close to main stores, freeway and good restaurants "
The price is €135
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Windsor Wine Country, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (749)
"Simplemente ideal en todo sentido… 10/10"
The price is €126
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Windsor Wine Country, an IHG Hotel

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1037)
"Property was very nice. Brian at the front desk was excellent. I stayed in an accessible studio beautiful spacious. Only thing I saw that needed to be fixed was inside the bathroom on the walls. Either mold mildew something towards the ceiling. "
The price is €139
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Windsor - Sonoma Wine Country
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Dom Whitney Tasting Lounge, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What are some of the best holiday rentals that Windsor has to offer?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This holiday home rental outside of Windsor is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Windsor?

Choose from 52 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Windsor Golf Club and Sonoma-Cutrer Vineyards Cutrer Vineyard are other places to visit while you're in town.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.