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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windsor holiday rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (140 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is ฿3,289
฿3,750 total
includes taxes & fees
9 Dec - 10 Dec
Wildhaven Sonoma Glamping
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

2. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
4.0 out of 10, (1 review)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
The price is ฿8,391
฿9,650 total
includes taxes & fees
16 Nov - 17 Nov
Hideaway Cottages
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

3. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is ฿2,658
฿3,031 total
includes taxes & fees
11 Nov - 12 Nov
The Ranch at Lake Sonoma
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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Find holiday rentals that suit your style

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Top Windsor Hotel Reviews

A fountain with water spouting from the top, surrounded by a circular pool.
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Windsor

8/10 Good

We only stayed the one night as we were travelling around but, check in was easy, plenty of parking and for value it was hard to beat. We had a family room which was big enough that we were not kicking the beds moving around. Breakfast was buffet and the usual variety. Timings meant the tables were very busy.
United Kingdom
Simon
Reviewed August 11, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently Asked Questions

Can I find holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Powell's Sweet Shoppe - Windsor, 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.

How many holiday rentals are there in Windsor?

Choose from 30 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards 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.