House holiday rentals in Windsor

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Popular amenities for Windsor house rentals

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 stars3 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
Top Guest favourite
Home in Forestville
4.99 out of 5 average rating, 116 reviews

Giusti Ranch, by Vinifera Homes

RitwikRating, 5 stars2 weeks ago
I had a wonderful stay! The place was absolutely beautiful — peaceful, well-maintained, and full of charm. The pool was a lovely spot to relax, and being able to walk through the surrounding vineyards made the experience feel extra special. Everything was thoughtfully documented, which made it easy to settle in and explore. The host’s recommendations were very helpful and much appreciated.
Superhost
Home in Sebastopol
4.88 out of 5 average rating, 101 reviews

Serene Wine Country Retreat with Pool & Hot Tub

ShanaRating, 5 stars2 months ago
I almost don't want to tell you how good this place is, so we can rent it again sometime. :-) But it's that good. We visited over spring break with our daughters, eight and 11, and had one of the most amazing stays we've ever had at an Airbnb. The home, the land, the pool, and the local area are all 100% amazing. And the sunsets. You know how you sometimes stay at Airbnb's where you feel like the hosts did the bare minimum to qualify to list it? This is *not* that place. There is everything you need and more. Thank you so much SatKartar!
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 stars2 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 Sebastopol
4.98 out of 5 average rating, 177 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

TessRating, 5 stars2 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
4.96 out of 5 average rating, 187 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

JoseRating, 5 stars2 weeks ago
10/10 I stayed here with my girlfriend and my dog and it was really peaceful and had a great time,the pool and jacuzzi was amazing and the house was really clean🙌🏽😄
Guest favourite
Home in Santa Rosa
4.98 out of 5 average rating, 124 reviews

Sonoma Green House *Pool*Close to Wine Country

DawnRating, 5 stars2 weeks ago
Conveniently located, lovely decorated home. Quiet neighborhood with access to downtown Santa Rosa, wine country, Russian River, Healdsburg, and more. Comfortable accommodations with everything you need. We spent afternoons floating in the pool after wine tasting. The property owner communicated well and responded quickly when messaged.
Guest favourite
Home in Sebastopol
4.91 out of 5 average rating, 128 reviews

The Deer Retreat – Privacy and Comfort

KristenRating, 5 stars3 weeks ago
We were in town for a family wedding. Dave's house was just beautiful! Very private with beautiful grounds! We were fortunate enough to have great weather and were able to take advantage of the pool, which was lovely. The bathrooms were all beautifully redone. The beds were HEAVENLY! We were unable to take advantage of the many recommendations because we had family obligations, but they were plentiful! The location of the house is just perfect... less than 2 miles into the center of Sebastopol and less than 30 mins to some great excursions! Would absolutely stay here again!

Weekly house rentals

Guest favourite
Home in Sebastopol
4.9 out of 5 average rating, 824 reviews

Wine/Apple Country Cottage, Centrally Located

DongjinRating, 5 stars1 week ago
This accommodation is clearly the work of someone with incredibly refined taste and a great sense of style. From the moment I stepped inside, I could feel the beauty in every part of the space. I truly appreciated the attention to detail—even the smallest things were thoughtful and delightful. The neighborhood is peaceful, with many beautiful and charming areas nearby, along with plenty of great restaurants. Overall, the entire experience was truly a happy one.
Top Guest favourite
Home in Bodega Bay
4.99 out of 5 average rating, 288 reviews

The Beach House

LoisRating, 5 stars3 weeks ago
This home has the most beautiful views and the house is wonderful as well. The furnishings were cozy, clean and comfortable. We had a fantastic stay and wished we could stay longer. Would definitely stay again if we are ever back in the area.
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 stars5 days 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!
Guest favourite
Home in Santa Rosa
4.96 out of 5 average rating, 206 reviews

Beautiful & Cozy Home in Historic Cherry St!

RashaRating, 5 stars3 weeks ago
Had a great stay at Rachel’s unit. She was easy to communicate with and very accommodating. Shared lots of recommendations in advance. The house is super clean and very well decorated. Beds were super comfortable and bathroom & kitchen spotless. So many coffee shops and restaurants within walking distance of unit and Sonoma vineyards just minutes away. Would absolutely stay again.
Top Guest favourite
Home in Sebastopol
4.96 out of 5 average rating, 406 reviews

Sebastopol Guest House

SusanRating, 5 stars3 weeks ago
We were beyond satisfied with Wendy and Lisa’s Guest House. The garden path and the private patio were lovely and once we entered the guest house, all was clean and peaceful and very nicely decorated. Watching the hummingbirds and orioles feed outside our bedroom window was a bonus! Wendy and Lisa provided us with some great suggestions regarding restaurants and sightseeing in the area. We look forward to returning.
Guest favourite
Home in Forestville
4.96 out of 5 average rating, 141 reviews

Hilltop Haven 🌅 view & hot tub

DanRating, 5 stars2 weeks ago
Thank you for the stay - we enjoyed the Champagne and my wife saw a mother and baby fox off the back deck one morning. Cute place, nice deck, fenced outdoor space for the dogs, very well appointed kitchen. There are 2 stairs down to the bedrooms and 2 stairs up to the kitchen and bath, but there is automatic lighting at night which helps with the navigation.
Guest favourite
Home in Santa Rosa
4.97 out of 5 average rating, 183 reviews

Cul-de-Sac | King | BBQ | Stocked | Washer+Dryer

DhananjayRating, 5 stars2 weeks ago
The place was clean and well stocked. We had a great time BBQing one night and enjoyed the hot tub. It is close to wineries and other attractions. The host was very communicative and all instructions were clear and easy to follow. Definitely recommend this home for stay if you are visiting Santa Rosa.
Guest favourite
Home in Santa Rosa
4.97 out of 5 average rating, 35 reviews

Near Healdsburg, Sonoma County Wine Retreat

ArdelleRating, 5 stars4 days ago
It was a very great experience for my family. We thought the place was beautiful and roomy The price was very reasonable and we all agreed that we would stay there again

Private house rentals

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

Luxurious Healdsburg Home Walk to Wineries

ReginaRating, 5 stars3 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!
Guest favourite
Home in Forestville
4.95 out of 5 average rating, 62 reviews

Russian River Luxury Escape | Private Hot Tub

MatthewRating, 5 stars4 days 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 stars2 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 Healdsburg
4.99 out of 5 average rating, 98 reviews

Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger

MollyRating, 5 stars1 week ago
Loved staying at Sarah’s beautiful home! The location was convenient but private, the house was spacious and peaceful, and especially loved the relaxing sauna! Thanks for a lovely visit!
Guest favourite
Home in Healdsburg
4.96 out of 5 average rating, 27 reviews

Puccioni Paradise

TracyRating, 5 stars3 weeks ago
What a wonderfully serene staycation! It was the perfect place to relax and unwind after Bottlerock. We really appreciated Debi's (host) excellent communication, and found all the instructions for check-in, check-out, and the house manual to be very clear and helpful. The location was ideal for us – it felt secluded and peaceful, yet being less than 15 minutes from downtown Healdsburg was so convenient. We also found the home to be very clean, cozy, and spacious, which made our stay extremely comfortable. Just a note for future guests: while the separate cottage is a great addition, the only bathroom is located inside the master suite in the main house. This might be something to consider for two couples, as it requires going through the bedroom to access it. However, it's perfectly suited for one couple or a small family with children. We will definitely be adding WC Lodging to our list of favorite places for future winery getaways!
Superhost
Home in Windsor
5 out of 5 average rating, 12 reviews

Sunny Retreat Near Golf Course w/ Hot Tub 4BD

BeccaRating, 5 stars2 weeks ago
Amazing value for Sonoma county. Ample space in the house, very clean, beautiful greenery in the backyard makes you feel secluded even though you’re in a neighborhood, comfortable and homey without feeling like someone’s house they live in. Reminds me of a classic vacation rental with standards pre-Airbnb days. The hosts are phenomenal. Very communicative. I expressed that we had brought coffee beans and that we couldn’t find a coffee grinder - they dropped a brand new one off for us to have the next morning! …. Even more amazing, we accidentally left some bottles of wine in a tote bag. Their team coordinated with my brother who lives in the area and dropped the goods off to him. Just all around really thoughtful hospitality. Great place, highly recommend. We were in town for a nieces birthday party, so didn’t do much wining and dining, but would be a great launchpad for a group who has that on their agenda. Return to this quiet oasis and hot tub after a day out in Sonoma county!
Top Guest favourite
Home in Geyserville
5 out of 5 average rating, 60 reviews

Spectacular views from hot tub

ChristopherRating, 5 stars2 weeks ago
Had a wonderful experience on the top of the hill. Views were spectacular and the hot tub was placed perfectly for sunsets and star gazing. Wish I had booked more nights!
Guest favourite
Home in Santa Rosa
4.99 out of 5 average rating, 90 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

NickRating, 5 stars3 weeks 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!

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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  2. United States
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  4. Sonoma County
  5. Windsor
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