Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

9.2 out of 10, Wonderful, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is NZ$617
includes taxes & fees
27 Jan - 28 Jan
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
8.4 out of 10, Very good, (6 reviews)
"Stayed here for a wedding "
United States
Lanna E.
The price is NZ$1,611
includes taxes & fees
9 Feb - 10 Feb
Elegant Vineyard Living at a Private Wine Country Estate

Camping in Geyserville

The Ranch at Lake Sonoma
1.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Nice camping spot "
United States
Evelyn
The price is NZ$114
includes taxes & fees
27 Jan - 28 Jan
The Ranch at Lake Sonoma

Mobile Home in Guerneville

Tranquil Redwood Retreat
8.8 out of 10, Excellent, (10 reviews)
"We had a lovely stay at the Tranquil Redwood Retreat! The cabin was clean, cozy, and beautifully decorated—just like the photos. The kitchen was fully stocked with everything we needed, and the check-in process was smooth and easy. It was the perfect spot for a peaceful getaway surrounded by nature. We made some great memories here and would definitely love to come back!"
United States
Stacie L.
The price is NZ$528
includes taxes & fees
28 Jan - 29 Jan
Tranquil Redwood Retreat

Cottage in Middletown

Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is NZ$333
includes taxes & fees
27 Jan - 28 Jan
Backyard Garden Oasis
3.5 star property
8.6 out of 10, Excellent, (27 reviews)
"Beautiful quiet retreat "
United States
Belwadi
Mandala Springs Wellness Retreat Center
2.0 star property
The price is NZ$415
includes taxes & fees
27 Jan - 28 Jan
Rouge Cobb Mountain Hotel - Cabin 1
9.6 out of 10, Exceptional, (65 reviews)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
The price is NZ$618
includes taxes & fees
28 Jan - 29 Jan
Wine Country Cottage in downtown Santa Rosa, CA

Holiday Home in Scenic Brush Creek

2 Hidden Wine Country Gem Upstairs Unit
9.8 out of 10, Exceptional, (22 reviews)
"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 NZ$450
includes taxes & fees
29 Jan - 30 Jan
2 Hidden Wine Country Gem Upstairs Unit
3.0 star property
The price is NZ$726
includes taxes & fees
27 Jan - 28 Jan
Russian River Retreat! Woodsy Guerneville Bungalow

Holiday Home in Cobb

Cobb Mountain Chalet Main For
9.6 out of 10, Exceptional, (14 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is NZ$290
includes taxes & fees
8 Feb - 9 Feb
Cobb Mountain Chalet Main For
10.0 out of 10, Exceptional, (18 reviews)
"Great location and comfortable stay. "
United States
HEATHER T.
Charming Dog-Friendly Home Near Regional Park
10.0 out of 10, Exceptional, (2 reviews)
"Yard was great for our dog. "
United States
Kip K.
The price is NZ$448
includes taxes & fees
4 Feb - 5 Feb
Charming NEW studio with AC and private yard in tranquil Sebastopol
10.0 out of 10, Exceptional, (4 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is NZ$647
includes taxes & fees
27 Jan - 28 Jan
2BR Bungalow | Russian River & Wine Country
9.0 out of 10, Wonderful, (2 reviews)
"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 NZ$428
includes taxes & fees
2 Feb - 3 Feb
Sebastopol Lux Walk toTown Guest Suite
10.0 out of 10, Exceptional, (6 reviews)
"Had a good time here, home is cozy and clean "
United States
James D.
The price is NZ$753
includes taxes & fees
8 Feb - 9 Feb
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

Holiday Home in Northwest Santa Rosa

Winemaker's Delight: 3BD/3BA Russian River Valley
9.8 out of 10, Exceptional, (72 reviews)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is NZ$722
includes taxes & fees
9 Feb - 10 Feb
Winemaker's Delight: 3BD/3BA Russian River Valley

Cabin in Guerneville

The Tiny Tipsy Turtle
10.0 out of 10, Exceptional, (46 reviews)
"Great location to walk to town!"
United States
Brenda R.
The price is NZ$324
includes taxes & fees
2 Feb - 3 Feb
The Tiny Tipsy Turtle
10.0 out of 10, Exceptional, (62 reviews)
"This cottage was so cute! So close to the beach, super comfortable beds, and Valerie was an awesome host! This is a must stay if you are looking for a place in Dillon beach "
United States
Lauren S.
The price is NZ$939
includes taxes & fees
2 Feb - 3 Feb
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
10.0 out of 10, Exceptional, (18 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is NZ$765
includes taxes & fees
27 Jan - 28 Jan
Bright and modern - Water views - Close to 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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$114 per night. Entering your travel dates in the search wizard you might find 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 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?

Casa Bella Estate in Wine Country w/ New Pool!: This holiday home rental outside of Windsor is located in a rural location, and has a fireplace, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 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.