Photo by Jennifer Hill

Windsor Holiday Rentals

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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
Fridge, microwave, oven, stovetop
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, (48)
"The villa was a great way to celebrate my wife’s 65th birthday with our closest friends. When everyone walked into the main house they all asked where the camera crew was coz this was like being at the Bachelor mansion! There was so much to do there that we didn’t have enough time to take advantage of all the amenities like the gym and media room. We had a game night in the wine cave as well as a catered dinner in there and it was amazing! If we had any questions or troubles the staff was...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
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
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Property grounds
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (157)
"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.
Outdoor pool, a heated pool
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
10.0 out of 10, Exceptional, (113)
"Amazing property and views perfect for 5 couples. We will be back!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
Outdoor dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (199)
"The house was gorgeous, but the views still take the cake. The kitchen is stocked full of everything you could need to cook in, you won't want to leave! William was responsive, and provided plenty of information to guide your stay."
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Living area
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (205)
"Our short stay could not have been better....well, unless a deer had come to visit! But we had turkeys, birds, and squirrels each morning which we enjoyed from the comfort of the living room since it was a little chilly. Eric has thought of everything, and we felt as though we were in a 5 star resort! Well done!"
New Modern House in Sonoma Valley's Best Area
Interior
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (196)
"Love this house. Close to town and everything. Plenty of room for everyone."
The price is HK$12,868
per night
28 May - 29 May
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Property grounds
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (324)
"Love it"
Oceanfront - Hot Tub - Newly Remodeled Cottage
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
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
Property grounds
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, (268)
"Jujube was perfect for my husband and I and our 2 labs. It’s so close to everything you would want; coast, redwoods and wineries. The dogs loved the river access and small beach a few doors down. Highly recommend this small but well equipped cottage. Thank you Bridgette for sharing your place!"
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Sun-loungers, beach towels
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
9.8 out of 10, Exceptional, (185)
"👍 great place and location"
The price is HK$2,098
per night
29 May - 30 May
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
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
Smart TV, fireplace, DVD player, books
Waterfront 2 bed 2 bath with the BEST VIEWS
9.8 out of 10, Exceptional, (305)
"Awesome!"
The price is HK$2,279
per night
23 May - 24 May
Waterfront 2 bed 2 bath with the BEST VIEWS
Fridge, microwave, oven, stovetop
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
9.8 out of 10, Exceptional, (11)
"Cute little river house. Comfortable bed, newly remodeled, clean interior. Has most amenities for cooking (bring your own seasonings). Hot tub works well but turn it up when you arrive so it's hot when you want to use it. Tight driveway, don't recommend a full size truck. Definitely would stay here again."
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
Aerial view
Bodega Bay on the Edge of Pacific Ocean
9.6 out of 10, Exceptional, (99)
"Close to everything I love about Bodega Bay."
Bodega Bay on the Edge of Pacific Ocean
Property grounds
Wildwood Gardens Scenic Vacation Retreat on the River
9.6 out of 10, Exceptional, (167)
"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
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 HK$2,948
per night
23 May - 24 May
Safari West
Don't see what you're looking for?
See all available properties in Windsor
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

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 HK$1,187
per night
28 May - 29 May
Hampton Inn & Suites Windsor - Sonoma Wine Country
Exterior
Holiday Inn Windsor Wine Country, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (559)
"Super friendly staff and a clean hotel. The sink in our room was slow to drain and the bath faucet took awhile to heat up to temp, but, beside those issues, things were fine!"
The price is HK$993
per night
27 May - 28 May
Holiday Inn Windsor Wine Country, an IHG Hotel
Exterior
WorldMark Windsor
3.0 star property
9.0 out of 10, Wonderful, (270)
"Really beautiful place. Would stay here again. "
WorldMark Windsor
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.

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.

Recent reviews of Windsor properties
Expedia verified reviews

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

5/5 Excellent
"Comfortable room,great bedding"
A verified traveller from Kingston stayed at Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
Posted 1 day ago
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel