A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor holiday rentals

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

1. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is AU$1,569
includes taxes & fees
25 Oct - 26 Oct
Sauna, Cold Plunge & Fire Pit Near Wineries
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

2. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is AU$1,544
includes taxes & fees
27 Oct - 28 Oct
Elegant Vineyard Living at a Private Wine Country Estate
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (136 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is AU$159
includes taxes & fees
23 Nov - 24 Nov
Wildhaven Sonoma Glamping
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

4. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is AU$580
includes taxes & fees
29 Oct - 30 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Private kitchen

5. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is AU$523
includes taxes & fees
1 Nov - 2 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A wooden structure with a circular entrance, a small table, and a sofa outside a house.

6. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is AU$659
includes taxes & fees
16 Nov - 17 Nov
Forestville Redwood Escape
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

7. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
The price is AU$634
includes taxes & fees
1 Nov - 2 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A deck with outdoor seating, a grill, and a view of a house with large windows.

8. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (38 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is AU$717
includes taxes & fees
1 Nov - 2 Nov
Somms Rest ⎮ Designed. Curated. Peaceful.
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

9. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (43 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
The price is AU$760
includes taxes & fees
27 Oct - 28 Oct
Serenity at the Russian River
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

10. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (10 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is AU$770
includes taxes & fees
26 Oct - 27 Oct
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

11. Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
The price is AU$478
includes taxes & fees
2 Nov - 3 Nov
Peaceful, charming, cottage in wine country. Beautiful yard!
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

12. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
The price is AU$792
includes taxes & fees
29 Oct - 30 Oct
Wine Country Getaway
A wooden interior with a dining area, a bench, and a mirror on the wall.

13. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (29 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is AU$676
includes taxes & fees
26 Oct - 27 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
A swimming pool with a slide, a barbecue area, and a wooden deck.

14. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 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 AU$397
includes taxes & fees
26 Oct - 27 Oct
2 Hidden Wine Country Gem Upstairs Unit
A modern kitchen with a central island, bar stools, and a dining table set with candles.

15. Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!

Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"We had an excellent stay and will definitely keep this place in mind for future stays. The rooms were spacious and everything was well appointed. We enjoyed the hot tub and the swings on the front porch. An overall great place. "
United States
Emily N.
The price is AU$788
includes taxes & fees
2 Nov - 3 Nov
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
A hot tub on a wooden deck with a view of a forested area.

16. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (10 reviews)
"Very unique and charming property. Definitely felt like being in a tree house in the redwoods. We spent most of our time when there sitting on the deck. It was conveniently located to everything we wanted to do - drive to the coast, hike at the state park, and visit nearby restaurants and wineries."
United States
Sherri
The price is AU$612
includes taxes & fees
26 Oct - 27 Oct
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

17. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (76 reviews)
"Our stay was very comfortable."
United States
Kim R.
The price is AU$853
includes taxes & fees
2 Nov - 3 Nov
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

18. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (84 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is AU$754
includes taxes & fees
27 Oct - 28 Oct
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

19. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.8 out of 10, Exceptional, (8 reviews)
"Nice camping spot "
United States
Evelyn
The price is AU$128
includes taxes & fees
26 Oct - 27 Oct
The Ranch at Lake Sonoma
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

20. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"Wonderful vacation and location. "
United States
Leslie M.
River View Lodge - Hot Tub and Tastings Included
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

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

10/10 Excellent
"Very easy access from 101. Room was spacious and clean. Bed very comfortable. It was handy having fridge microwave and toaster oven. Great price"
Barbara 1-night trip
Posted 2 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

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$128 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 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.

What are some of the best holiday rentals that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This holiday home rental outside of Windsor is located on the waterfront, and has a balcony, a selection of books and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.