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Windsor Holiday Rentals

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Holiday Rentals in Windsor

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Bodega Bay
9.8 out of 10, Exceptional, (467)
"View was amazing!"
United States
Liz T.
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Oceanfront - Hot Tub - Newly Remodeled Cottage

Bodega Bay
9.8 out of 10, Exceptional, (406)
"Great location and amenities here. Easy to get to local attractions we wanted to do. I'd stay here again."
United States
Tom B.
Oceanfront - Hot Tub - Newly Remodeled Cottage

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Kenwood
10.0 out of 10, Exceptional, (243)
"Absolutely beautiful and fun getaway with family and friends. We can't wait to come back next year. "
United States
Judy W.
The price is AU$3,690
includes taxes & fees
29 Dec - 30 Dec
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Panoramic Ocean View--3 Min Walk To Beach

Dillon Beach
9.6 out of 10, Exceptional, (333)
"Great place to stay-- great ocean view, close walk to the beach. "
United States
Cynthia L.
Panoramic Ocean View--3 Min Walk To Beach

The Ranch at Lake Sonoma

1.0 star property
Geyserville
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$102
includes taxes & fees
8 Dec - 9 Dec
The Ranch at Lake Sonoma

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Bodega Bay
9.2 out of 10, Wonderful, (220)
"Great location "
United States
jerry d.
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Bodega Bay on the Edge of Pacific Ocean

Bodega Bay
9.6 out of 10, Exceptional, (165)
"Very nice place. Spacious, clean and cosy"
United States
bruno f.
Bodega Bay on the Edge of Pacific Ocean

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Monte Rio
9.8 out of 10, Exceptional, (354)
"Lovely, comfortable getaway!"
United States
William H.
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

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

St Helena
10.0 out of 10, Exceptional, (252)
"Wonderful home, perfect place for a family of all ages! "
United States
Anonymous traveller
The price is AU$3,022
includes taxes & fees
8 Dec - 9 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood
9.6 out of 10, Exceptional, (136)
"Lovely property. Pool was perfect for families with small children. Outdoor amenities are first rate. Comfortable bedding, well-equipped kitchen. Perfect setting for a large family gathering."
United States
Nita R.
Casa Bella Estate in Wine Country w/ New Pool!

Bright, quiet home with amazing ocean/bay view, private hot tub & beach access

Bodega Bay
8.6 out of 10, Excellent, (59)
"Blue Horizon is a clean, comfortable place to stay for a family vacation. The dining room and living room have a great view of the ocean, and you can walk to the beach (less than a half-mile walk)."
United States
Susan H.
Bright, quiet home with amazing ocean/bay view, private hot tub & beach access

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Old Town Bodega Bay
9.4 out of 10, Exceptional, (352)
"Loved this property and the views. "
United States
anne
The price is AU$840
includes taxes & fees
11 Dec - 12 Dec
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Luxury Napa Estate With Pool/Hot-tub/Concierge

Calistoga
10.0 out of 10, Exceptional, (50)
"Perfect location for a wine weekend. "
United States
John W.
The price is AU$3,303
includes taxes & fees
8 Dec - 9 Dec
Luxury Napa Estate With Pool/Hot-tub/Concierge

Waterfront Home in Bodega Bay! 3Beds, 2Baths & panoramic ocean views.

Old Town Bodega Bay
9.6 out of 10, Exceptional, (23)
"Ideal house in a great location. This totally for our family's needs and was the perfect spot for us to relax in. "
United States
Jana S.
Waterfront Home in Bodega Bay! 3Beds, 2Baths & panoramic ocean views.

Escape to Wine County in your independant Cottage in Downtown Calistoga

Calistoga
9.6 out of 10, Exceptional, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
The price is AU$548
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Wine County in your independant Cottage in Downtown Calistoga

Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

Dillon Beach
9.0 out of 10, Wonderful, (310)
"Wonderful stay, perfect for my wife and I and our 16 and 12 year old boys and our small dog. Just steps from the beach and a perfect location and set up. Thank you for a great stay!"
United States
Stuart G.
Ocean Front/3 minute walk/Hotub/Sauna/Pets/Massage Chair/Pinball/Pac-Man Machine

~ Home w/Gas Fireplace + 3 Cottages w/Baths + Hot Tub ~ Pool ~ Pet Friendly ~

Guerneville
9.8 out of 10, Exceptional, (47)
"The space was cool and rather well designed for privacy and community. We appreciated the clean rooms and outdoor space. Thanks for this vacation time and hope to stay again some time!"
United States
Ryan D.
~ Home w/Gas Fireplace + 3 Cottages w/Baths + Hot Tub ~ Pool ~ Pet Friendly ~

The Tiny Tipsy Turtle

2.0 star property
Guerneville
10.0 out of 10, Exceptional, (41)
"Great location to walk to town!"
United States
Brenda R.
The price is AU$295
includes taxes & fees
8 Dec - 9 Dec
The Tiny Tipsy Turtle

Backyard Garden Oasis

3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is AU$351
includes taxes & fees
8 Dec - 9 Dec
Backyard Garden Oasis

Incredible Ocean Front Home with 3 Master Suites and Secluded Beach

Dillon Beach
10.0 out of 10, Exceptional, (243)
"We had a fabulous time. Property owner was very communicative and took great care of us. Great home, great owner!"
United States
Matthew R.
Incredible Ocean Front Home with 3 Master Suites and Secluded Beach
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$102 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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?

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 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.