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Windsor Holiday Rentals

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Holiday Rentals in Windsor

Luxury Estate Awaits: Your Ultimate Vineyard Escape
10.0 out of 10, Exceptional, (1)
"Stayed here for a wedding "
United States
Lanna E.
The price is AU$1,923
includes taxes & fees
18 Nov - 19 Nov
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43)
"Very well maintained"
United States
Jim M.
The price is AU$868
includes taxes & fees
12 Nov - 13 Nov
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
The Ranch at Lake Sonoma
1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
United States
Tamara
The price is AU$139
includes taxes & fees
23 Oct - 24 Oct
The Ranch at Lake Sonoma
Enchanting Retreat in the heart of Redwoods
8.8 out of 10, Excellent, (12)
"The property/rental itself is vety nice and well appointed. However, the location leaves a little to be desired. It's essentially a trailer park and not the "nestled in the redwoods" place we were thinking it would be. Property owner/manager was very responsive throughout the rental process."
United States
Tim L.
The price is AU$534
includes taxes & fees
18 Nov - 19 Nov
Enchanting Retreat in the heart of Redwoods
Tranquil Redwood Retreat
8.8 out of 10, Excellent, (10)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is AU$533
includes taxes & fees
30 Oct - 31 Oct
Tranquil Redwood Retreat
Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is AU$332
includes taxes & fees
23 Oct - 24 Oct
Backyard Garden Oasis
Sebastopol Lux Walk toTown Guest Suite
10.0 out of 10, Exceptional, (1)
"This is a wonderful place to stay in Sebastopol. It is comfortable, cosy, quiet and well appointed - comparable to a suite in a nice hotel. There is good access, parking and a great location. Everything worked perfectly. The only issue is that entry to the room is via a spiral stair case that would be difficult for some people with disabilities. "
United States
Joe B.
The price is AU$379
includes taxes & fees
27 Oct - 28 Oct
Sebastopol Lux Walk toTown Guest Suite
Mandala Springs Wellness Retreat Center
3.5 star property
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
United States
Belwadi
The price is AU$387
includes taxes & fees
23 Oct - 24 Oct
Mandala Springs Wellness Retreat Center
Cobb Mountain Chalet King Size Suite
9.4 out of 10, Exceptional, (24)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is AU$218
includes taxes & fees
27 Oct - 28 Oct
Cobb Mountain Chalet King Size Suite
Rouge Cobb Mountain Hotel - Cabin 2
3.0 star property
The price is AU$340
includes taxes & fees
3 Nov - 4 Nov
Rouge Cobb Mountain Hotel - Cabin 2
Glen Ellen Retreat #1 Hot Tub and King Beds
10.0 out of 10, Exceptional, (73)
"Extremely nice property in lovely quaint Glen Ellen."
United States
Heidi M.
The price is AU$611
includes taxes & fees
28 Oct - 29 Oct
Glen Ellen Retreat #1 Hot Tub and King Beds
The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (37)
"Everything about the place was perfect. Close to shops, dining, and activities!"
United States
Jamey A.
The price is AU$318
includes taxes & fees
26 Oct - 27 Oct
The Tiny Tipsy Turtle
NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi
10.0 out of 10, Exceptional, (1)
"The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative."
United States
Beth G.
The price is AU$598
includes taxes & fees
27 Oct - 28 Oct
NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
10.0 out of 10, Exceptional, (1)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Bright and modern - Water views - Close to beach
10.0 out of 10, Exceptional, (15)
"Our stay at Kellie's Dillon Beach home was so very comfortable and had everything we needed. Super comfortable bed, awesome kitchen and loved the patios!"
United States
Nancy F.
The price is AU$779
includes taxes & fees
26 Oct - 27 Oct
Bright and modern - Water views - Close to beach
2 Hidden Wine Country Gem Upstairs Unit
9.8 out of 10, Exceptional, (21)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is AU$486
includes taxes & fees
18 Nov - 19 Nov
2 Hidden Wine Country Gem Upstairs Unit
Escape to Wine County in your independant Cottage in Downtown Calistoga
9.6 out of 10, Exceptional, (28)
"Great cottage near downtown. "
United States
Tim L.
The price is AU$626
includes taxes & fees
2 Nov - 3 Nov
Escape to Wine County in your independant Cottage in Downtown Calistoga
Creekside Cozy 2BR 1BA + 2 Acres
2.0 star property
9.6 out of 10, Exceptional, (4)
"Cute place. Great location. Property manager was helpful and responsive. Can't wait to return!"
United States
Shannon A.
The price is AU$664
includes taxes & fees
23 Oct - 24 Oct
Creekside Cozy 2BR 1BA + 2 Acres
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
9.4 out of 10, Exceptional, (18)
"My boyfriend and I loved our stay at this cottage, so much so that we're still talking about it weeks later. The space is small but very well thought out with everything you need for a cozy stay. It sits up from the quiet road, surrounded by trees, and feels very private. The deck and fireplace were nice, and the bed was very comfortable. The decor is also so much nicer than what you find in most rentals and we appreciated that too. Highly recommend for a romantic stay for two!"
United States
Ellie W.
The price is AU$564
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Riverside love shack
2.0 star property
The price is AU$675
includes taxes & fees
30 Oct - 31 Oct
Riverside love shack
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$139 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

7 Bedroom Oceanfront in Dillon Beach with spa: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 32 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 Pacific Coast Air Museum 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.