Photo by Jennifer Hill

Windsor Vacation Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Vacation 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
Save an average of 15% on thousands of hotels when you're signed in
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 CA $514
CA $586 total
includes taxes & fees
May 22 - May 23
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)
"Five girlfriends stayed for two nights. The best part of this house is the views. The house is very spacious, with plenty of room. Kitchen has everything necessary for cooking coffee, etc. but seriously needs updating - very old barely functional kitchen cabinets. Lots of stairs, so I would not recommend for seniors or little children, there could be some falls. Overall, we had a great time and the vacation home was very reasonably priced."
The price is CA $632
CA $1,133 total
includes taxes & fees
May 30 - May 31
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)
"Lovely"
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
9.6 out of 10, Exceptional, (10)
"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
Pool
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, (28)
"Beautiful location. Very clean. Awesome if you had a dog!"
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
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.

Windsor Vacation Rental Travel Info

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)
"Jetted tub left dirty ring, had to shower after seeing it. Manager had an attitude to person ahead of me. No coffee at breakfast. Did have luggage carriers. Disabled access was nice."
The price is CA $209
CA $234 total
includes taxes & fees
May 27 - May 28
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, (548)
"Great friendly staff "
The price is CA $225
CA $252 total
includes taxes & fees
May 27 - May 28
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 CA $207
CA $232 total
includes taxes & fees
May 23 - May 24
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers 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's the top vacation rental that Windsor has to offer?

COZY Bungalow--Dog-Friendly—Perfect for Couples!!! : You might want to consider this vacation home rental near Windsor, which 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 vacation rentals are there in Windsor?

Choose from 66 Expedia vacation rentals in Windsor for a memorable vacation.

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 vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.

Recent reviews of Windsor properties
Expedia verified reviews