Photo by Jennifer Hill

Windsor Holiday Rentals

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Holiday Rentals in Windsor

Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (88)
"Great house, no issues. "
Cottage home near the Russian River; county parks; numerous wineries
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay. The property is gorgeous and the house was great for a group with places for everyone to be together or separate when needed. We only have a few recommendations. First, the driveway is quite steep and curvy. A caution on that especially if you drive a larger vehicle as we did. We never could get the hot tub to heat up, even after contacting the host. Instructions for that were not in the guest book. Even though the host walked us through it, having it written down would...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (343)
"Breathtaking views and lovely house! Sunsets from the hot tub were my favorite!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.6 out of 10, Exceptional, (147)
"Great little private bungalow perfect for couples as advertised. We gad a great stay here and will be staying here again. "
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (212)
"We really enjoyed the location and the overall aesthetic of the house. It's clean and had everything we needed for a long relaxing weekend."
The price is AU$3,436
includes taxes & fees
9 Oct - 10 Oct
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH
9.2 out of 10, Wonderful, (178)
"We enjoyed the walks to the beach, 2 beaches, and the view of the ocean from the house. House layout worked well for our group that included 7 people as well as 2 dogs. Enjoyed hot tub together. Went to town one day, lots of games. Would recommend, except for very small kitchen."
The price is AU$1,280
includes taxes & fees
3 Oct - 4 Oct
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, (287)
"Lovely cabin. We enjoyed our stay very much. The river view was very relaxing and we enjoyed the privacy. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (394)
"We had the best time celebrating our one year anniversary over Labor Day weekend at Aftermath. We were very excited that the property was pet friendly so we could bring our best boy, Gunther, with as well!! The views from house are breathtaking and we loved being able to walk to the beach to play ball with Gunther. Our favorite part was enjoying the sunsets from the hot tub after dinner. Very clean, well stocked and the perfect location. We can’t wait to come back and are already planning our...
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (227)
"Enjoyed staying at this property. So tastefully decorated. Loved the deer and wild turkeys roaming around the grounds. "
New Modern House in Sonoma Valley's Best Area
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
9.2 out of 10, Wonderful, (156)
"The house has lots of games and cooking supplies you will need. Hot tub was nice. The location is perfect. You can walk to the beach. I would not count the women’s cave near the hot tub as additional bedding to sleep. It looks like people have been using it for their dogs to sleep. However, there is more then enough space to add air mattress on the floor. We had a great time. And the property is perfect for a large family or group of friends."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
9.8 out of 10, Exceptional, (190)
"Wonderful and close to everything Bodega Bay! Attentive and friendly host"
The price is AU$909
includes taxes & fees
21 Oct - 22 Oct
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
Bodega Bay on the Edge of Pacific Ocean
9.6 out of 10, Exceptional, (112)
"My family and I had a lovely stay at this cozy Bodega Bay home. The house had everything we needed and the host was so kind and communicative. The dunes and beach are a very short walk just out the back door. We thoroughly enjoyed our stay and highly recommend!"
Bodega Bay on the Edge of Pacific Ocean
Stunning Views of CA Coast : Beautifully Remodeled Home
9.8 out of 10, Exceptional, (313)
"Comfortable living room, nice sound system (bring your own tunes), well equipped kitchen. We had a mix of sunny and foggy days, spent most of the time relaxing in the house. Quiet neighborhood. Everything as described in the listing accurate. "
Stunning Views of CA Coast : Beautifully Remodeled Home
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (207)
"William's property was a spectacular property that sits literally above the clouds (at least the bucolic cloudline in the morning that blankets the valley floor vineyards). So much space to enjoy the outside (from swings, to pickleball/basketball courts, to hikes, to the pool), and a peaceful and welcoming inside. William was also a wonderful host - very responsive and kind. 10 out of 10."
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
8.4 out of 10, Very good, (35)
"The home is very well equipped for those traveling with dogs, but we did not. Also given that it is dog friendly, I'd say the house was very clean. Kitchen is very well equipped especially if you want to bake, and the beds were comfortable. Location was a little difficult to find because we arrived at night but we managed. It's a great spot if you are exploring the area and just need a home base, but nothing special. Hot tub was nice during the day surrounded by trees but was difficult to figure...
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
Waterfront 2 bed 2 bath with the BEST VIEWS
9.8 out of 10, Exceptional, (314)
"Loved sitting on the deck, which is right over the water, watching all the wildlife in and around the water. We felt very at home the minute we walked in. It's minutes from so many beaches and places to explore. Steve and Krista are wonderful host and are always available if you have questions. As many have said the driveway is a little tricky to maneuver but if you follow the instructions exactly as worded you will have no problem. Would definitely stay again! "
The price is AU$979
includes taxes & fees
6 Oct - 7 Oct
Waterfront 2 bed 2 bath with the BEST VIEWS
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (175)
"Ms. Jackie was very responsive and her home was most accommodating to our stay. She provided excellent recommendations and clear instructions. We thoroughly enjoyed our time in her home. There were 6 of us and 2 of us shared a bed in the master bedroom. Overalll great, comfortable location. "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (219)
"Awesome house in the perfect location. So well equipped with everything needed, had coffee, bottled water, soft drinks, a bottle of wine and beer for us upon arrival!! Jim also provided information on local restaurants, wineries and tours that very helpful. Jim was also very responsive to questions. We hope the house is available for our next trip to St Helena."
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
9.6 out of 10, Exceptional, (176)
"We enjoyed our stay at the property. The only downside was the lack of hot water in the shower. Otherwise nice!"
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Spacious Yet Cozy Bodega Bay Experience!
8.8 out of 10, Excellent, (226)
"The house is very unique and had a lot of vintage items throughout the home. Beautiful view from the deck area. Property is located right next to Duncan's Cove where there is a dog friendly beach. Also the sunsets are just incredible if you drive all the way down to the end of Duncan's Cove. Some things to consider when renting the property: 1. Location is right on Hwy 1 - didn't notice a lot traffic noise but made me a little nervous having our dog so close to the main road. 2. Backyard is...
Spacious Yet Cozy Bodega Bay Experience!
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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.
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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, (1000)
"Everything was excellent. My only observation is that the bathroom vent system in room #106 needs to be checked out as it does not remove odors or steam from the bathroom. Our friends in room #220 noticed the same issue. Staff was excellent as everything else. A "First class" operation! "
The price is AU$254
includes taxes & fees
1 Nov - 2 Nov
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, (689)
"Convenient location to stay in Sonoma wine country."
The price is AU$210
includes taxes & fees
14 Oct - 15 Oct
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, (1000)
"I’m happy thank you very much"
The price is AU$255
includes taxes & fees
28 Oct - 29 Oct
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 top-notch restaurants and wineries. 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 51 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.