House holiday rentals in Windsor

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Windsor

House rentals with a pool

Guest favourite
Home in Glen Ellen
4.91 out of 5 average rating, 176 reviews

Luxury home, hot tub/spa pool, walk to restaurants

LaurenRating, 5 stars2 weeks ago
Linda’s place was great. It was clean and comfortable and the location was great. A quick walk into the adorable town of Glen Ellen. The backyard is gorgeous and the spa pool was a fun perk to enjoy.
Guest favourite
Home in Healdsburg
4.91 out of 5 average rating, 107 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

EmilyRating, 5 stars5 months ago
We really enjoyed our stay, very private and quiet. Great location among the wineries of northern Sonoma County. Kitchen was great, and we enjoyed the fireplace every evening. Thank you!
Superhost
Home in Sonoma
4.91 out of 5 average rating, 117 reviews

Spectacular Stone Pool/Spa with Views; Near Plaza

KristineRating, 5 stars4 weeks ago
Summers House is exceptional! And the views and gardens are amazing. Pat was very responsive, and her detailed instructions and local recommendations were very helpful. Don't be hesitant about the short drive up to the house. It is beautiful drive, and the location is worth it.
Top guest favourite
Home in Forestville
4.99 out of 5 average rating, 107 reviews

20 Acre Ranch w/Vineyards, Pool, Hot Tub, & Views!

SophiaRating, 5 stars3 days ago
This house/Airbnb is amazing! Host communication was great and helpful. Every corner and furniture was pristine clean. House style is perfect for any kind of vacation stay. We were a group of 4 friends and 3 of us came with our babies/toddler. High chair and crib was super helpful. Kitchen is fully stocked to whip up any kind of meals (simple or complicated). We enjoyed many of the amenities including hot tub, fire pit, brand new high end grill. The property sits on a beautiful 20+ Acers of vineyard, we took walks every morning and evening. Even got lemons 🍋 from the garden and added to our water. We enjoyed going to wineries within 5-10 mins away as well as Napa and Sonoma wineries. Highly recommend anyone to book this Airbnb if you’re looking for a worry free, comfortable, clean, and beautiful wine country get away.
Guest favourite
Home in Sonoma
4.88 out of 5 average rating, 302 reviews

*Heated* Swimming Pool Retreat Near Sonoma Square

RyanRating, 5 stars2 months ago
The house was exactly as described and comfy. Plenty of room for 8, and in a quiet neighborhood. We didn’t use the pool but it looked so inviting for summertime! Great place to stay with a group. Thanks!
Superhost
Home in Sebastopol
4.91 out of 5 average rating, 100 reviews

Luxury home (+ pool house) with views, pool & spa

MeganRating, 5 stars1 month ago
Absolutely beautiful place to gather with old friends. The house is even bigger than it looks and everyone had plenty of space and privacy, with lots of communal spaces when we wanted to gather. The setting is gorgeous and it's easy to get into town or visit wineries. We would definitely come back!
Superhost
Home in Santa Rosa
4.87 out of 5 average rating, 215 reviews

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Lisa And StephenRating, 5 stars1 week ago
Great host, location and the house was perfect for what our group needed. We really enjoyed our time in Santa Rosa. We did not cook in the kitchen but you could see it was well stocked with everything needed to prepare a nice meal. The front room accommodated the six of us easily. Would definitely stay at this property again!
Superhost
Home in Guerneville
4.83 out of 5 average rating, 178 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

KiranRating, 5 stars1 month ago
Griselda was a wonderful host. Our stay was super last minute and she was very accommodating, responsive and flexible. The location was perfect. We came to hike in Armstrong Redwood Park and her place was only about a 3 min drive there. It was also a three minute drive from the downtown so great location. Beautiful house with lots of space and a huge yard. I'd love to come back in the summer when we could use the outdoor space more, but the hot tub was perfect for the winter.

Weekly house rentals

Guest favourite
Home in Cloverdale
4.87 out of 5 average rating, 113 reviews

Woodhawk Manor of Alexander Valley

MichaelRating, 5 stars8 months ago
Beautiful property that worked well for our group. Great pool and the views and amazing. The kitchen is well stocked. The host (Rob) is very helpful and responsive and can help work through any issues. Highly recommend!
Superhost
Home in Monte Rio
4.91 out of 5 average rating, 335 reviews

Family Friendly Charming 2 BD

ColeenRating, 5 stars1 week ago
This was our second time staying at Casa Sophia! It was clean, well-equipped, and very cozy. Would absolutely come back again.
Guest favourite
Home in Healdsburg
4.89 out of 5 average rating, 112 reviews

Healdsburg 2br Cottage with Private Yard!

HaileyRating, 5 stars3 months ago
This was the perfect spot for our quiet weekend. I usually prefer not to use guesthouse Airbnbs but this one was totally private and felt like entirely its own space. Super clean, cozy, and comfortable. We’ll be back!
Guest favourite
Home in Guerneville
4.93 out of 5 average rating, 184 reviews

Escape to Guernevilla, sunniest spot on the river!

ClaraRating, 5 stars3 days ago
A great trip! We were having a "moms weekend" away from the kiddos and felt very comfortable to relax, soak in the hot tub, and cook food in a great well-stocked kitchen. The kitchenware was high-quality, great cabinet of spices, and didn't at all feel like an empty rental. We also appreciated how many kids books and toys were available even without our kids there. Books for grown ups, too! And it was a nice treat to have a car charger.
Superhost
Home in Windsor
4.87 out of 5 average rating, 130 reviews

Charming Windsor Home

ChrisRating, 5 stars6 days ago
This is a nice detached cottage, with a complete kitchen, and bedroom. It was very conveniently located for us, with visits to breweries and wineries all near. Nicely decorated. This is a residential neighborhood, so there are dogs that bark at all hours. The ac is not built-in, not a mini-split, but instead a portable unit set up in the living room. It cools the living and kitchen just fine, but the cool air has to navigate into the bedroom, and that takes a while. The only real complaint is that if you are there during a rain event, the water drips onto something that makes a lot of noise in the bedroom, and makes it hard to sleep. No rain, no issue
Superhost
Home in Bodega Bay
4.85 out of 5 average rating, 121 reviews

BodegaBayBeachHome:UpscaleBeachHome!Ocean&Beaches!

AnnRating, 5 stars1 day ago
Beautiful house so close to the ocean. Loved having the fireplace to bring warmth during the cold wet weather. The locally made brownies were amazing. Stace was very helpful and responsive. Additional lounge was great for the teenagers.
Superhost
Home in Santa Rosa
4.93 out of 5 average rating, 144 reviews

West End Neighborhood Cottage

NancyRating, 5 stars2 months ago
A perfect place to stay ! The cottage is so warm and cozy, extremely clean, so many nice amenities. It’s back from the street so it’s very quiet - with a beautiful green space in front with a table to sip morning coffee. I love the split bathroom - shower in one room and toilet/sink in another room. The kitchen is spacious , the bedroom has a big closet, the kitchen is perfect, and the living room area is so comfortable. Laundry room is close and there is great driveway parking. It is truly a wonderful place to stay !
Guest favourite
Home in Sonoma
4.93 out of 5 average rating, 111 reviews

Wine Country Escape with 4 King beds & hot tub!

KristinRating, 5 stars1 week ago
Really enjoyed our stay here while visiting wineries in Sonoma and Napa! The place felt like home and was very well appointed with everything we needed. We brought our 1 year old son along and they had many baby items we were able to use and it was easy to keep the main living area pretty baby safe for a kiddo on the move. Location was great, quiet neighborhood but still close to many wineries and downtown Sonoma. Just be aware of strict noise policy at nighttime so don’t plan to use the hot tub/fire pit super late at night. Overall was a great stay and would stay again if we come back!

Private house rentals

Guest favourite
Home in Sonoma
4.94 out of 5 average rating, 463 reviews

Thornsberry House, A Luxe Wine Country Getaway

KiaraRating, 5 stars2 weeks ago
This home is very modern and beautiful. I came with three other friends to stay over a weekend and we found that the amenities were great in the location suited what we needed. This is not a complaint, but I just want folks to be aware that all that glass doesn't have any curtains on it, which is beautiful, but if it makes you feel uncomfortable, that's worth knowing. Everything was great! Truly.The only improvement could be if there's a full length mirror somewhere in the house where you can like see yourself. We possibly missed it, but we definitely searched for it.
Superhost
Home in Santa Rosa
4.79 out of 5 average rating, 100 reviews

Annadel Retreat| Hot Tub | Trails | Views | Wine

AlinaRating, 5 stars1 month ago
This is a second time we are staying in Annadel House Retreat for little getaway in wine county. The place is just amazing! Spacious, everything you need it there, views are stunning. Nikki is super host in terms on communications. We are planning to stay again net year. Highly recommend!
Top guest favourite
Home in Sonoma
4.97 out of 5 average rating, 129 reviews

Large Charming Home Surrounded by a Vineyard

VenaRating, 5 stars1 month ago
So responsive very helpful we really enjoyed the property and would book again the hot tub was fantastic
Guest favourite
Home in Sebastopol
4.92 out of 5 average rating, 118 reviews

The Deer Retreat – Privacy and Comfort

AbigayleRating, 5 stars3 months ago
Our family had a wonderful stay here for the holidays! The house was perfect, so much space for the dogs outside too. We will be back!
Guest favourite
Home in Santa Rosa
4.96 out of 5 average rating, 115 reviews

Mountain top, wine country escape

CarlosRating, 5 stars1 month ago
We had a fantastic stay at this Airbnb! The place is peaceful, beautiful, and offers plenty of privacy—perfect for a relaxing getaway. My wife and I, along with our dog, truly enjoyed our time here. Our pup had lots of space to roam safely, which was a huge plus for us. The location is also great—secluded enough to feel like a retreat, yet conveniently close to Santa Rosa. Alexa was an amazing host, providing thoughtful recommendations that made our stay even better. We highly recommend this place to anyone looking for a tranquil escape!
Guest favourite
Home in Guerneville
4.92 out of 5 average rating, 182 reviews

Riverside Lodge House in Guerneville

JeanelleRating, 5 stars2 weeks ago
Beautiful Place, Quiet & Peaceful. The Kitchen was stocked with plenty of dishes, utensils & glassware. Our group of 10 felt right at home. Thank You!
Superhost
Home in Santa Rosa
4.91 out of 5 average rating, 102 reviews

Wine Country Fairgrounds AC BBQ Downtown Stocked!

ReubenRating, 5 stars2 weeks ago
had a great time at Dan's place. close to everything. full kitchen with everything. was there to take of my son for post op knee surgery. so great to able to cook in a nice setup. Will most be back to enjoy another time in tbe future
Guest favourite
Home in Sonoma
4.91 out of 5 average rating, 251 reviews

Retro Retreat in the Sonoma Valley

NickRating, 5 stars2 weeks ago
Excellent location. The house was clean and exactly as described. It was the perfect location, easy to get to, and very smooth. Josette and Dave are professionals—they know EXACTLY how to make this an easy place to stay!

Quick stats about house rentals in Windsor

  • Total rentals

    90 properties

  • Total number of reviews

    5.4K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore

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  5. Windsor
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