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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

Top guest favourite
Home in Sonoma
4.95 out of 5 average rating, 477 reviews

Luxe WineCountry getaway with Pool, hottub & Bocce

KateRating, 5 stars4 weeks ago
Lovely home!! I will definitely be back. The outdoor shower was such a vibe, beautiful and comfortable furniture, lovely decor and close to town! Great place
Guest favourite
Home in Santa Rosa
4.97 out of 5 average rating, 106 reviews

Sustainable Luxury Barn - Secluded Sonoma Retreat!

AllesandraRating, 5 stars4 weeks ago
Gorgeous place and wonderful hosts. They made us feel like family and gave us the best recommendations. We’ll definitely be back!
Guest favourite
Home in Occidental
4.95 out of 5 average rating, 152 reviews

Modern mid-century-inspired, Deer Ranch

LaurenRating, 5 stars3 weeks ago
Amazing retreat in the Redwoods - the property is quiet, has beautiful views of the redwoods with both outdoor sun and shade spots, and has a cool interior. Pool was perfect for cooling off on a hot day. I would stay again! We stayed in May, and while the yard was mowed, it had a type of grass that was very prickly so not barefoot or dog friendly - so we weren’t fully able to enjoy the expansive yard space.
Guest favourite
Home in Santa Rosa
4.92 out of 5 average rating, 119 reviews

PrivateWarm&Cozy+Spa+Pool+FirePit+Wi-Fi!

AlexisRating, 5 stars3 weeks ago
We had a wonderful experience having a small family reunion here. We had two older adults who use walkers and a baby, so I wanted to make sure that the house could accommodate all of us. Place was perfect for this with 3 bedrooms on the first floor, and only a couple steps to manage into the front door. Robin and other hosts were really helpful in answering all of my questions prior to the booking (and after). Loved the pool, hot tub and gazebo sitting area. Used the grill for family dinners. Will treasure our memories here!
Top guest favourite
Home in Santa Rosa
5 out of 5 average rating, 110 reviews

Heated Pool+Hot Tub+Ping Pong, Close to Wineries

DianaRating, 5 stars1 week ago
Jenny's place was perfect for our girls trip! The large living space, pool and hot tub were a definite plus for our purpose. The beds were amazing and the house was fully stocked with all necessary items. Jenny was very responsive to any questions we had. We would definitely stay here again for a nice weekend getaway from the Bay Area.
Top guest favourite
Home in Sebastopol
4.98 out of 5 average rating, 177 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

TessRating, 5 stars3 weeks ago
I loved this place. It was beautifully decorated and had amazing views. The pool was an added benefit on hot days! It’s somewhat small for a group because it only has one bedroom but still worth the experience.
Guest favourite
Home in Santa Rosa
4.88 out of 5 average rating, 229 reviews

Heated Pool / Hot Tub. Walk to Shops, Wine, Food.

DennisRating, 5 stars3 weeks ago
Absolutely loved our stay! The place was spotless, beautifully decorated, and exactly as described. Stewart was friendly and responsive, making everything super easy. Would definitely stay again!
Top guest favourite
Home in Glen Ellen
4.96 out of 5 average rating, 189 reviews

Vineyard Stay • Walk to Wineries • Press Favorite

RaizyRating, 5 stars1 week ago
Bill is an incredible host! He is so kind and responsive, always trying to make your stay 10/10. The house is absolutely beautiful, peaceful, spotlessly clean, and well-stocked. If you want a truly peaceful and relaxing place to stay, with a kind and attentive host, this is the place you should stay!

Weekly house rentals

Top guest favourite
Home in Bodega Bay
4.99 out of 5 average rating, 290 reviews

The Beach House

JessicaRating, 5 stars1 week ago
Natalie's home is the absolute perfect place to stay in Bodega Bay. It's close to local restaurants, trails and the Lodge at Bodega if the spa, pool or dinner at Drakes is on your agenda! My husband and I both agree she truly has the best property in town, offering amazing views, close access to the beach and this location is easily commutable for day trips to Russian River Valley vineyards/wineries. As a plus, she provides a book on property that includes restaurant menus, top attractions in the area and every instruction you may need as it relates to the property. Kitchen is well stocked for those wanting to source their own fish at the local fish market and enjoy a meal at home. Our time here was magical!
Top guest favourite
Home in Healdsburg
5 out of 5 average rating, 34 reviews

Vineyard Oasis: Luxury Home in the Heart of Sonoma

DarcyRating, 5 stars1 week ago
Super great location near Windsor and 12 minutes from Healdsburg. Easy check in, lovely view, and comfortable beds. Fenced in yard as well. Would definitely go back!
Top guest favourite
Home in Santa Rosa
4.95 out of 5 average rating, 602 reviews

Craftsman 2 blocks from Russian River Brewery!

ShawnRating, 5 stars1 week ago
An amazing host, house, and location!
Guest favourite
Home in Sebastopol
4.97 out of 5 average rating, 262 reviews

Sonoma County Historical Ranch House on a Vineyard

JuanRating, 5 stars2 weeks ago
My girlfriend (now fiance) and I loved this home. It was beautiful to wake up and look in the backyard and just see a vineyard everyday. Pretty much has anything and everything you could think about needing at a home! The grill and hot tub were great to use! We took this time to celebrate our anniversary while also getting engaged at a winery nearby. The drive to the town was short and there was a gas station just right before going in. The privacy of the location is great and really gave us that comfortable setting to where we could be ourselves.
Top guest favourite
Home in Marshall
4.99 out of 5 average rating, 225 reviews

Tomales Bay: Tranquility, Bay Views, Kayaks &

JamieRating, 5 stars1 week ago
This was our second stay at BayMod, and we're already excited to come back again. It's a stunning location, right on the bay, with kayaks and all the accessories you'd need (like lifejackets in many sizes). We saw seals, bat rays, and lots of other wildlife when we went out in the morning. We love going to Nick's Cove for lunch and outdoor games (you could even kayak there), to Route One Bakery for breakfast and coffee, and down to Point Reyes Station for shops, restaurants, and groceries. The house is impeccably organized (the most well-organized Airbnb I've ever seen) with helpful instructions and just everything you might think of. Example: lying on the couch looking out the window and feeling a bit cold? There is a bin of throw blankets within arm's reach. Trying to see what's on Hog Island right now? There are binoculars, plus a powerful monocular with a phone mount. This thoughtfulness extends to all aspects of the house. It's beautiful, clean, and cozy. Thank you Deb!
Guest favourite
Home in Santa Rosa
4.96 out of 5 average rating, 205 reviews

Centrally Located, Modern Wine Country Estate

RyanRating, 5 stars4 weeks ago
Our stay at Ted’s in Santa Rosa was great! We enjoyed our trip to wine country - the backyard was a perfect space for our dogs to run around and for us to enjoy a glass of wine on the patio. The house was very clean, comfortable, and well stocked for our trip. Would stay here again!
Guest favourite
Home in Santa Rosa
4.95 out of 5 average rating, 133 reviews

3 Bedrooms 1 Bath | Quiet House

JohnRating, 5 stars3 weeks ago
Spacious living room, well equipped kitchen, Tamara's home makes a great basecamp for exploring all that Santa Rosa and Sonoma County have to offer.
Guest favourite
Home in Windsor
4.97 out of 5 average rating, 59 reviews

Heart of Wine Country, Cute Cottage w/Hot Tub

DanielleRating, 5 stars1 week ago
Came here for a Father’s Day weekend with the family. We were seeing a concert at Bacchus Landing in Healdsburg which was only a 10 minute drive from the place. Location has DT Windsor nearby and Santa Rosa / Healdsburg are not far away. Clean and comfortable space for 4 people! Would stay here again.

Private house rentals

Luxe
Home in Healdsburg
5 out of 5 average rating, 18 reviews

Luxurious Healdsburg Home Walk to Wineries

ReginaRating, 5 stars4 weeks ago
An indoor/outdoor living dream! The pool/hot tub/pool house/covered patio area was perfect and was where we spent most of our time during the day. Loved how private and peaceful the surrounding area was, while also being walking distance to wineries and a short drive to Healdsburg square. Home was spacious and everyone slept comfortably. Our family loved this Airbnb so much that we’ve already booked our next stay!
Luxe
Home in Santa Rosa
4.97 out of 5 average rating, 38 reviews

Luxury Villa, Pool, Spa, BBQ, By Healdsburg

StephanieRating, 5 stars1 week ago
Gorgeous location and property! Hossna is extremely friendly and responsive. We had a fantastic stay and can’t wait to come back!
Superhost
Home in Healdsburg
4.9 out of 5 average rating, 80 reviews

Morning Dew - A Riverfront Healdsburg Home

MargaretRating, 5 stars1 month ago
This place was so quiet, private and beautiful. We got to see a huge deer right next to the house! Great back deck where we spent a ton of time play games ans drinking wine...nice big kitchen, really comfy beds! It is a ways outside of town so a car is necessary and the road there is pretty curvy and dark at night. Cell service is limited out there, but the wifi worked well. Over all our stay was great and our host was very responsive. Would definitely stay here again!
Guest favourite
Home in Forestville
4.95 out of 5 average rating, 62 reviews

Russian River Luxury Escape | Private Hot Tub

MatthewRating, 5 stars1 week ago
Kim's place was serene. The main living area looks into the backyard with lush bamboo and trees. The jacuzzi is tucked away from view of the house and itself is nestled under the canopy of trees. The kitchen is well stocked with pots, pans, and plates. Everything you need to make a meal (bring your own food). A grocery store is a 5 minute drive into Forrestville. We loved it.
Guest favourite
Home in Santa Rosa
4.99 out of 5 average rating, 79 reviews

Wine County Opulent Villa Pool/Hot Tub-Upper Level

AnashaRating, 5 stars3 weeks ago
We had the most amazing time at Carl’s stunning home. The house was even more beautiful than the pictures—spacious, perfectly designed, and filled with thoughtful details. The views were absolutely breathtaking, and the layout of the home made it easy to relax and enjoy every moment. The amenities were incredible—from the sparkling pool and relaxing hot tub to the Nespresso machine that made our mornings extra special. Carl was a fantastic host. We communicated by email before the trip, and he provided us with wonderful vineyard recommendations that turned out to be highlights of our stay. On our way out, we had the pleasure of meeting Carl in person, and he was just as kind and welcoming as we expected. This was truly a special experience in a truly exceptional home. We can’t recommend it enough and are already dreaming about coming back!
Top guest favourite
Home in Geyserville
5 out of 5 average rating, 61 reviews

Spectacular views from hot tub

AndersRating, 5 stars2 days ago
Jill was super communicative and showed us around when we arrived. The views from the hilltop are incredible and the outdoor spaces were awesome for hanging in the evenings with the dogs!
Guest favourite
Home in Santa Rosa
4.99 out of 5 average rating, 90 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

NickRating, 5 stars1 month ago
Amanda's place is absolutely the place you want to stay in. My girlfriend and I stayed here for her birthday trip to Napa and it definitely worth the money and time spent here. Location is perfect for both privacy and closeness to numerous surround long towns with tons to do and just a short drive to both Napa and Sonoma county The house itself is beautiful, extremely clean and organized, fantastic views from any location inside the house. Bedrooms were super comfortable with luscious space Multiple bathrooms made it great for getting ready to go out and about Kitchen has everything you need The property was great private but doesn't feel desolate The pool was great the hot tub was so relaxing The detached game room made for some great fun at the end of the nights All in all amanads place was amazing and I would absolutely recommend to someone staying in the area If I return I will definitely be rebooking this listing Thank you again for the great hosting!
Top guest favourite
Home in Santa Rosa
5 out of 5 average rating, 35 reviews

Adorable Cottage, Best Location!

OpalRating, 5 stars1 month ago
This was the second time we’ve stayed here. We decided to extend our vacation and the cottage was not available for the extra 5 nights. We were able to find another place a little further from our daughter’s home but, once you’ve stayed at this cottage, you’re spoiled! Not to say anything negative (we haven’t even spent one night in the second spot), but Christmas’s cottage is more spacious, more modern, far “homier”, has a washer and dryer, is sunnier, has personalized snacks/fruit/beverages, etc., etc. There just is no comparison! We were out and about all day, but definitely could have been comfortable spending more time in the cottage. A lot of thought has obviously gone into its design and how it is fitted out! You will not be disappointed, I can assure you!

Quick stats about house rentals in Windsor

  • Total rentals

    90 properties

  • Total number of reviews

    5.6K 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

    60 properties have a dedicated workspace

Destinations to explore

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  4. Sonoma County
  5. Windsor
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