Photo by Jennifer Hill

Windsor Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 | Outdoor pool, a heated 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
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 | Smart TV, fireplace, books, video library
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (203)
"Perfect spot to enjoy the wine country over the weekend. Central location and beautiful modern accommodations in a picturesque setting! Would stay here again!"
New Modern House in Sonoma Valley's Best Area
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
Exterior
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"
Chalk Hill Cottage Close to Wineries
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
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
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!
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
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
Upscale Vintage Cabin with Huge Sunny Deck nestled in the Redwoods
9.8 out of 10, Exceptional, (258)
"Loved the vibes of the house and location. Would definitely go back"
Upscale Vintage Cabin with Huge Sunny Deck nestled in the Redwoods
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
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
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
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 ￥58,424
￥66,603 total
includes taxes & fees
May 19 - May 20
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 ￥23,527
￥26,350 total
includes taxes & fees
May 29 - May 30
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, (550)
"Great friendly staff "
The price is ￥26,283
￥29,437 total
includes taxes & fees
May 22 - May 23
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 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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

5/5 Excellent
"Place was great! Clean, friendly staff, nice balcony with view.. loved it!"
A verified traveler stayed at Oxford Suites Sonoma County
Posted 20 hours ago
Oxford Suites Sonoma County