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Windsor Holiday Rentals

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Holiday Rentals in Windsor

Heart of Wine Country, Cute Cottage w/Hot Tub

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay in this home although it was very brief. A great location in Windsor. "
The price is AU$911
includes taxes & fees
22 July - 23 July
Heart of Wine Country, Cute Cottage w/Hot Tub

Wine Country Home of Healdsburg Wine Maker

9.6 out of 10, Exceptional, (22)
"What a wonderful place to call home while on vacation!!!! Cynthia and staff are amazing and added so much to our stay. Make sure you experience the Barn tasting…it was the highlight of our trip. Property is exactly as described and the location is perfect. "
Wine Country Home of Healdsburg Wine Maker

1 Block To St. Helena Main Street Shops-Restaurants! Avail May 26-29, July 6-9

10.0 out of 10, Exceptional, (257)
"This house is great and exactly as shown. Jill was incredibly thoughtful in her communication and we so appreciated that the checkout process was easy. Quick walk to town but the house was so perfect that we preferred staying in most nights for dinner! Would highly recommend. "
1 Block To St. Helena Main Street Shops-Restaurants! Avail May 26-29, July 6-9

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (235)
"Wonderful accommodations for a family weekend in the wine country!"
The price is AU$3,312
includes taxes & fees
23 July - 24 July
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Riverbed House with hot tub

10.0 out of 10, Exceptional, (1)
"I am on a non-profit board with 4 people on it. We needed to get our annual planning for 2025-26 done quickly and the best way to do that was to get away from our day-to-day lives and location.Linda's home is lovely, extremely comfortable and has ideal amenities and is a perfect balance between quiet and easily accessible.We had a great visit! Got a ton accomplished while having a great time. We truly felt relaxed even though we were busy nearly the whole time!Thank you so much for making us...
The price is AU$867
includes taxes & fees
3 Aug - 4 Aug
Riverbed House with hot tub

Love Shack private retreat

10.0 out of 10, Exceptional, (1)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
The price is AU$313
includes taxes & fees
21 July - 22 July
Love Shack private retreat

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
The price is AU$352
includes taxes & fees
20 Aug - 21 Aug
Garden house with gas fireplace

Tangerine Cottage spacious home

The price is AU$479
includes taxes & fees
29 July - 30 July
Tangerine Cottage spacious home

Charming 2-bedroom cabin with Wi-Fi included in Loch Lomond

The price is AU$612
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom cabin with Wi-Fi included in Loch Lomond

Luxury King Room with Jetted bath, Small Private Deck. Walk to Calistoga Spas

Luxury King Room with Jetted bath, Small Private Deck. Walk to Calistoga Spas

Expansive 2-Room King Suite, Walk to Downtown Calistoga

The price is AU$876
includes taxes & fees
23 July - 24 July
Expansive 2-Room King Suite, Walk to Downtown Calistoga

Napa Valley Retreat in Calistoga!

9.8 out of 10, Exceptional, (30)
"The place was clean and in a convenient location. Couches were uncomfortable, no cleaning supplies to wash dishes, and uncertain of check-out instructions. Minor things but a good stay over all"
The price is AU$695
includes taxes & fees
21 July - 22 July
Napa Valley Retreat in Calistoga!

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (18)
"Perfect place to stay, nice and cozy!"
The price is AU$224
includes taxes & fees
22 July - 23 July
Cobb Mountain Chalet King Size Suite

The Parlour House at the Fainting Couch

2.0 star property
The price is AU$1,236
includes taxes & fees
22 July - 23 July
The Parlour House at the Fainting Couch

Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi

The price is AU$1,016
includes taxes & fees
3 Aug - 4 Aug
Zoë Creekside-Tranquil Redwoods-20 wineries 3 mi

Glen Ellen Retreat #1 Hot Tub and King Beds

10.0 out of 10, Exceptional, (62)
"Great place to relax. Nice backyard with hot tub. "
The price is AU$670
includes taxes & fees
28 July - 29 July
Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #2 King Beds

10.0 out of 10, Exceptional, (141)
"Excellent property."
The price is AU$609
includes taxes & fees
29 July - 30 July
Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #3 King Beds

10.0 out of 10, Exceptional, (55)
"This was a wonderful place to stay and I highly recommend!"
The price is AU$690
includes taxes & fees
29 July - 30 July
Glen Ellen Retreat #3 King Beds

Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country

10.0 out of 10, Exceptional, (88)
"We met family for birthday celebration. Wine tours & wonderful food! Had a great time. The kitchen was well stocked with everything needed to cook for family. Too cold for pool but enjoyed hot tub, deck and yard. Location close to all 7 wineries we visited. Highly recommend."
The price is AU$1,638
includes taxes & fees
3 Aug - 4 Aug
Wine Country Farmhouse with pool & spa in heart of Sonoma Wine Country

heiter house- a kenwood gem, private, hot tub with views, and centrally located

8.0 out of 10, Very good, (1)
"We had two couples head to Napa for a short trip. Such a cute cottage and perfect for Sonoma excursions. Napa requires going over or around the mountains but it’s not bad. Hot tub was great. Cottage was well appointed. Coffee pot is on the small side for 3 coffee drinkers. No complaints. Helpful binder of info. Bedrooms were spacious. Primary bath could be updated but certainly enough room. "
heiter house- a kenwood gem, private, hot tub with views, and centrally located
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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Top Windsor Hotel Reviews

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 wineries and top-notch restaurants. 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?

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!: This holiday home rental outside of Windsor is located on the waterfront, and offers a selection of books, WiFi and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Windsor?

Choose from 40 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 La Crema Estate at Saralee's 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.