Photo by Jennifer Hill

Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Property grounds
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (78)
"Great property that is close to hiking and wine country. Enjoyed our stay and would recommend."
Cottage home near the Russian River; county parks; numerous wineries
Exterior
1890s Historic Gem: Casa Dela Esperanza - 6BD/4BA
10.0 out of 10, Exceptional, (3)
"This house was absolutely perfect for a girls get away weekend. It was so clean and beautiful and the host was super responsive and accommodating. I don't have a bad thing to say about this experience- it was absolutely perfect!!"
1890s Historic Gem: Casa Dela Esperanza - 6BD/4BA
Pool
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (371)
"The cottage is cozy, the view is sublime, That's why we return time after time."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
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Fridge, microwave, oven, stovetop
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, (47)
"The Villa and location are absolutely stunning! The pictures are accurate, but do not do the property justice. It is a breath-taking view! Everything from the booking process to checking in was very easy. Randy was very polite, responsive, and accommodating with all of my questions and request. It was raining when we arrived, and Randy grabbed umbrellas for our whole group to do the property tour. No details were overlooked at this property. Chef Tiffany F. came to the house and prepared...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Beach
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.4 out of 10, Exceptional, (131)
"The Bay Bungalow was a perfect choice for us! Every accommodation was there for us. Felt like we were at a little hotel of our own. Loved everything!"
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Exterior
Safari West
2.0 star property
9.4 out of 10, Exceptional, (219)
"Incredible experience!"
The price is €397
per night
19 May - 20 May
Safari West
Property grounds
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (324)
"Love it"
Oceanfront - Hot Tub - Newly Remodeled Cottage
Property grounds
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
9.2 out of 10, Wonderful, (156)
"This Bodega Harbor home has incredible unobstructed views of the ocean with large windows from the kitchen and living room areas. It is a spacious house with cozy sitting nooks and plenty of board games/billiards/spa. The dining area is large but the only drawback is a small kitchen area. However, it has plenty of kitchenware with quality small and large appliances for your cooking needs. The outside front sitting area has comfortable adirondack chairs and seems to be somewhat wind protected....
The price is €787
per night
30 May - 31 May
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
Property grounds
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, (267)
"My experience was delightful, and I would highly recommend this little cottage to anyone looking for a peaceful getaway amidst nature's splendor."
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Property grounds
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
8.0 out of 10, Very good, (7)
"This funky, spacious property was just perfect for two couples for a cycling holiday. We loved hanging out in all the social spaces, inside and out. The river was great to cool off in. The routes inland, south in the forests, and west to the coast are excellent for road biking. The gardens were beautiful & the fencing made parking & setting up the bikes secure. We appreciated the hot tub after one misty ride. We had no problems with rodents, since we kept all our food in the fridge. We had a...
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
Fridge, microwave, oven, stovetop
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
9.8 out of 10, Exceptional, (11)
"The house was well placed, near Guerneville, restaurants and activities. Beautiful views from the top deck."
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
TV
Bright, quiet home with amazing ocean/bay view, private hot tub & beach access
8.4 out of 10, Very good, (32)
"We had our friends from out of town. They were amazed at the beautiful view. The house was perfect for our event. Walking around the neighborhood was lovely. We will be back again. This was our 4th time renting your beautiful home."
Bright, quiet home with amazing ocean/bay view, private hot tub & beach access
Outdoor dining
Wine Country Harvest Vacation Home
9.8 out of 10, Exceptional, (57)
"This was our second stay at the property. Very comfortable for our group of six. Easy access to wine tastings and great deli nearby for our picnic lunches"
Wine Country Harvest Vacation Home
TV, fireplace, video games, DVD player
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
9.2 out of 10, Wonderful, (148)
"We enjoyed our stay at this lovely and comfortable home! The view was spectacular and the restaurant had delicious food! Would definitely stay here again"
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
Beach
Bird Watcher Paradise 2 Bedroom 2 Bath with Beautiful View
9.8 out of 10, Exceptional, (116)
"Wonderful views enhanced by recent tree trimming. Wonderful kitchen enhanced by recent new oven. Fabulous sunroom. Great new cement for parking. In general a comfortable place to stay."
Bird Watcher Paradise 2 Bedroom 2 Bath with Beautiful View
3 bedrooms, Internet, bed sheets
Dog-friendly wine country Home on four scenic acres with private hot tub & pool
8.4 out of 10, Very good, (28)
"60th birthday couldn’t have been better. Amazing house."
Dog-friendly wine country Home on four scenic acres with private hot tub & pool
Property grounds
Wildwood Gardens Scenic Vacation Retreat on the River
9.6 out of 10, Exceptional, (166)
"This was a perfect place for us! 4 adults and one 5yo. Cabin and yard are very charming and private. Short drive to the coast with beautiful beaches and the river is awesome. Just around the corner from the cabin is access to a river beach. Would definately book here again."
Wildwood Gardens Scenic Vacation Retreat on the River
Property grounds
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (156)
"Booked this for my once yearly trip with a friend from 5th grade - we are both 60 this year. Also travelled with my 4 year old shepherd-rottweiler mix. The three of us LOVED the home. So many lovely touches; the owner is very gracious and responsive. The yard is something out of a wine country magazine. Absolutely gorgeous and lots of areas to relax. The beds and pillows are super comfortable (my friend and I are both super picky about comfort). The home temperature was easy to control. We...
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Pool
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, (15)
"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
Property grounds
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
8.6 out of 10, Excellent, (29)
"Beautiful location. Very clean. Awesome if you had a dog!"
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
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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.

Other types of properties in Windsor you may be interested in

Courtyard
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1002)
"The jacuzzi was down and pool did not look clean"
The price is €146
per night
29 May - 30 May
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
Exterior
Holiday Inn Windsor Wine Country, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (551)
"Great friendly staff "
The price is €175
per night
23 May - 24 May
Holiday Inn Windsor Wine Country, an IHG Hotel
Exterior
Hampton Inn & Suites Windsor - Sonoma Wine Country
2.5 star property
9.2 out of 10, Wonderful, (1000)
"We had an excellent stay. Will stay here again in the future"
The price is €156
per night
23 May - 24 May
Hampton Inn & Suites Windsor - Sonoma Wine Country
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.

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, apart-hotels, 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 €397 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?

COZY Bungalow--Dog-Friendly—Perfect for Couples!!! : This holiday home rental outside of Windsor is located on the waterfront, and offers a selection of books, a Smart TV and free WiFi 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 66 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 Sonoma-Cutrer Vineyards Cutrer 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.

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Expedia verified reviews