Photo by Jennifer Hill

Holiday Rentals in Windsor

Holiday Rentals in Windsor

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

9.8 out of 10, Exceptional, (7)
"We had a group of 12 ranging in age from 12 to 93 and we all had a wonderful time. The kitchen was well stocked and accommodated multiple cooks for an extensive dinner. The indoor and outdoor games were enjoyed by all ages. The common area was large enough for everyone to enjoy time together, without being cramped or constraining. The front veranda was such a pleasant place to hang out with our morning coffee. The back yard and rear deck had so much available to do that we never got a...
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

9.2 out of 10, Wonderful, (185)
"Felicity's home was the perfect place for our retreat. The common spaces were spacious allowing eight of us to easily come together in the comfortable abundant seating in the main living space and around the dining table. The four bedrooms all contained comfortable warm bedding and mattresses with an extra private room for one of us. The hot tub was clean and heated perfectly -- a big plus we look for in our annual retreats. IN addition, it was a true pleasure communicating with Felicity...
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (302)
"JuJuBe, the house we stayed in for our getaway, was warm and cozy, efficient and well appointed in all things, including kitchen utensils, linens, small appliances, and the like. We stayed during the "atmospheric river" storm and watched the Russian River just down from us rise and swell, yet we were happy in the warmth of the house and always felt quite safe. Great communication with the owner. We'd like to go back when we can take advantage of the available kayaks and outdoor deck. Really a...
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (221)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is €2,087
includes taxes & fees
5 Jan - 6 Jan
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (67)
"Very niche home with plenty of space inside and out. Lots of space to gather. Convenient location close to grocery shopping and restaurants. "
Wine Country Harvest Vacation Home

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (411)
"We absolutely adore this property – this has to be our ninth or 10th time back to it. Wonderful home comforts and amazing views— the family history is the cherry on the top."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (239)
"Loved this little get-away in an amazing location! Driving up country roads with red and gold vineyards on your right and left in autumn was amazing. And yet, so close to all the best Sonoma wineries!!! The house itself was thoughtfully decorated, with all you need for a wonderful Sonoma escape. We will definitely be back!!!"
New Modern House in Sonoma Valley's Best Area

The St. Helena House

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (215)
"Our stay at the Kenwood country estate was a wonderful and memorable experience! The property was private and secluded and exactly as listed. We stayed over Thanksgiving week and although our food was catered, we found all the entertaining essentials to complement our meal and make us feel right at home. The weather was warm, so we were able to join in the local Turkey Trot, play pickle ball on the well equipped courts, ride bikes on local trails, and enjoy morning yoga while taking in the...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

10.0 out of 10, Exceptional, (125)
"This house has everything and comes well stocked! Love that each bedroom has a king bed and its own bathroom! It’s perfect for groups! The kitchen was well stocked with platters, drink ware, bar essentials, etc. Also, the views are spectacular! We loved our stay! "
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Valley of the Moon Getaway

10.0 out of 10, Exceptional, (221)
"Great outdoor space with great views"
Valley of the Moon Getaway

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

9.6 out of 10, Exceptional, (157)
"the bungalow is charming and cozy and very well appointed. Our dog enjoyed the fenced yard and we all enjoyed our short walks to the water’s edge and harbor. Pamela was a gracious host with good recommendations for restaurants in Bodega Bay. We will be returning in the near future. Johanna"
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

1 Acre with 3 homes in the heart of wine country with last minute specials!

9.6 out of 10, Exceptional, (28)
"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "
1 Acre with 3 homes in the heart of wine country with last minute specials!

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (162)
"This property was as advertised. Met or exceeded our expectations. Nice neighborhood."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!

9.4 out of 10, Exceptional, (321)
"This place is truly lovely. Marine life is all around you. Views are breathtaking and the Boat House restaurant is practically next door. (Delicious) We enjoyed our stay so much. Very comfortable bed and every need was easily met. This place is absolutely beautiful!!! "
The price is €547
includes taxes & fees
5 Jan - 6 Jan
Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (39)
"Great place to stay. Conveniently located for our needs."
The price is €224
includes taxes & fees
5 Jan - 6 Jan
Comfort and Style in Our Queen Cottage

Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly

8.4 out of 10, Very good, (36)
"Amazing property with great place for doggies to run. Beautiful hot tub set among the redwoods. Clean and cozy with lots of great movies and video games and extra bedding and towels. We will recommend this place to all our friends. "
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (354)
"Stayed here for our 10th wedding anniversary. We loved it. Close to town and Bodega Head trails was breathtaking. We loved the hot tub! The views of the sunset and stars while enjoying the spa were worth the trip. If you’re looking for a quiet getaway with spectacular views, this is the spot!!!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Windsor you may be interested in

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

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Very professional and clean nice area to stay to enjoy wine country. "
The price is €124
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Windsor Wine Country, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (811)
"Clean and nice"
The price is €105
includes taxes & fees
11 Jan - 12 Jan
Holiday Inn Windsor Wine Country, an IHG Hotel

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Spacious room, very clean and cozy."
The price is €144
includes taxes & fees
1 Feb - 2 Feb
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.

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?

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella: This holiday home rental outside of Windsor is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 45 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 Pacific Coast Air Museum 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.