Cottage holiday rentals in Windsor

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Popular amenities for Windsor cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Guerneville
4.98 out of 5 average rating, 288 reviews

Hillside Retreat in the Redwoods w/ Hot Tub

MelanieRating, 5 stars1 week ago
David's home in the Guerneville redwoods was a magical place for a solo retreat. The beauty and attention to detail was wonderful - from the art to the amenities to the guidebook! David was very responsive and kind in his communications. Would stay again.
Superhost
Cottage in Guerneville
4.87 out of 5 average rating, 108 reviews

Guerneville Cabin Among the Redwoods + Wineries

DavidRating, 5 stars2 weeks ago
We loved Sarah and Keith’s house! Great location, close to everything, quiet, great neighborhood. We would definitely stay here again.
Top Guest favourite
Cottage in Santa Rosa
4.99 out of 5 average rating, 104 reviews

Story-Book Cottage in the Heart of Wine Country

HarryRating, 5 stars3 months ago
This is a charming place, beautifully kept with lovely furnishings. We really enjoyed the well appointed kitchen as we cooked every day. The yard and gardens are beautifully kept, peaceful and serene. Oranges growing right outside the house! We were in town for a wedding, and Santa Rosa is right in the middle of so many enjoyable things to do. We hiked on the CCT out past Bodega Bay, enjoyed restaurants in Healdsburg, visited the redwoods and shopped at the Barlow in Sebastopol. Thank you Cheryl for sharing your lovely home. We had a fabulous time!
Guest favourite
Cottage in Guerneville
4.91 out of 5 average rating, 352 reviews

Red Door Retreat

StephenRating, 5 stars2 weeks ago
This was our second time staying at Red Door Retreat and we had another great visit. As before everything was exactly as pictured and described. Checkin was very smooth and communication with Brett was great. We particularly enjoyed the several nice outdoor spaces and the hot tub. Quiet setting but short drive to local attractions and Guerneville town center. Highly recommended!
Top Guest favourite
Cottage in Santa Rosa
4.94 out of 5 average rating, 198 reviews

Napa Wine Country Retreat - Villa

BethRating, 5 stars5 days ago
My family and I had an enjoyable weekend stay at Peter’s cottage. The location was beautiful and home was cozy. The kitchen had everything we needed and I appreciated a clean porta-crib that was provided.
Top Guest favourite
Cottage in Monte Rio
4.97 out of 5 average rating, 189 reviews

Riverfront Cottage w/ lush gardens & hot tub!

KylieRating, 5 stars1 month ago
We had the most incredible stay at Mama K’s! The property is absolutely stunning, nestled right on the Russian River with gorgeous views and a sense of peace that’s hard to describe. From the moment we arrived, we felt completely relaxed and at home. Also, the wildlife was great to watch out for! Many deer, birds (even eagles!) and foxes! The space was spotless, cozy, and thoughtfully designed (lots of great updates!) with everything we needed. It was the perfect mix of comfort and charm, surrounded by nature’s beauty. Our dogs were in heaven! They loved exploring the property, lounging on the deck, and soaking up the fresh air. It’s not always easy to find a truly dog-friendly place that feels this special, but Mama K’s delivered on every level. We’re already planning our next visit. Thank you, Mama K, for sharing this magical place with us, we’ll definitely be back.
Guest favourite
Cottage in Monte Rio
4.88 out of 5 average rating, 210 reviews

Riverwood Cottage - Hot Tub, Direct River Access!

JanaRating, 5 stars5 days ago
Beautiful property! It was breathtaking to sit on the lawn and just hang out. So welcoming and had everything you could need
Guest favourite
Cottage in Monte Rio
4.92 out of 5 average rating, 353 reviews

Riverside Retreat in Monte Rio

AlexRating, 5 stars1 day ago
In a word - delightful! We very much enjoyed the back deck and patio with morning and afternoon sun, a relaxing yard with views of the river, osprey, swallows and even deer. The kitchen was very well equipped with high quality appliances/utensils/cookware/dishware etc for easy mealmaking. Playing records from Adam's collection was memorable & reminiscent. The beds were very comfortable - especially nice with french doors looking out to the back yard and riverscape. The location is easy distance from Monte Rio, Jenner and Guerneville, paddleboarding, beaching, hiking nearby plus nice to walk our dog Lexie in the extended neighborhood. Adam was a great host. We highly recommend Adam's delightful cottage retreat, and look forward to future stays!

Pet-friendly cottage rentals

Guest favourite
Cottage in Forestville
4.96 out of 5 average rating, 95 reviews

Private Wine Country Bungalow! Sunny Treetop Views

MichelRating, 5 stars3 weeks ago
What can I say, it was a perfect stay. For me, the mattress and overall sleep quality is very important and I can confidently say these have been THE MOST comfortable beds of any airbnb I’ve stayed in by a mile. Chad has every detail covered and is a great guy. It was a great experience overall, everything was high quality!
Superhost
Cottage in Sonoma
4.87 out of 5 average rating, 135 reviews

Historic Cuneo Cottage Downtown Sonoma

CarolineRating, 5 stars1 month ago
We had a wonderful girls’ weekend in Sonoma staying at this lovely cottage! The location is super walkable to both the square and to nice hiking trails. Everything was spotless and the beds were comfortable. Highly recommend!
Guest favourite
Cottage in Middletown
4.98 out of 5 average rating, 123 reviews

Garden house with gas fireplace

DanielleRating, 5 stars1 week ago
A wonderful, fun place to stay! Super comfy & looking forward to visiting again, soon!!
Guest favourite
Cottage in Santa Rosa
4.95 out of 5 average rating, 62 reviews

Steelhead Creek Vineyards Garden Casita

JessicaRating, 5 stars6 months ago
Had a wonderful stay at the vineyard & farm. It was incredibly peaceful. The home was very comfortable and inviting. Our 3 year old called it ‘light & bright’! 😂
Guest favourite
Cottage in Healdsburg
4.79 out of 5 average rating, 58 reviews

Charming Cottage in Healdsburg Wine Country

JodiRating, 5 stars3 weeks ago
We very much enjoyed our stay and loved the cottage and the surroundings immensely. Great communication with host easy to reach if any questions. Loved the yard space for bbq and the fire pit area and our dog felt comfortable. Very peaceful space and inside cottage very clean and felt at home. We visited many areas and sites from the cottage made for a good home base for us for our adventures. We have all great things to say about our time spent at the cottage and host. Very appreciative. Thank you very much!!
Guest favourite
Cottage in Dillon Beach
4.98 out of 5 average rating, 357 reviews

Dillon Beach Surf Cottage

SharonRating, 5 stars2 weeks ago
We had a wonderfully relaxing stay at Dennis and Dan’s amazing cottage! The view was amazing and the beach less than a 5 mins walk away. We walked down to the beach for long walks with our dogs twice daily, they had a ball! It’s wonderful to be able to let your dogs run off leash on a beach, there are so few places in CA that you can. We had planned on venturing out but found ourselves glued to the deck people watching, listening to the waves and chilling out. The cottage was immaculate! We’ve never stayed in a place that is so well stocked with everything you could possibly need. The hosts have literally thought of everything! We couldn’t leave without first booking for next year.
Guest favourite
Cottage in Glen Ellen
4.91 out of 5 average rating, 291 reviews

Cozy Creekside Retreat in Sonoma Wine Country

LizetteRating, 5 stars2 weeks ago
Amazing stay! Very peaceful, beautifully surrounded by nature, nice and quiet. Very spacious and super clean, great for travelers with dogs. Only advice: bring a flashlight as it gets very dark at night and it will help if you have to take the pups out around the vicinity and/or if you arrive late at night.
Guest favourite
Cottage in Cazadero
4.9 out of 5 average rating, 344 reviews

Gravenstein Cottage

GinaRating, 5 stars1 month ago
I had the very BEST stay at Mark's place! Everything about the stay was magical - the cottage was quaint and lovely, surrounded by redwoods. Mark's hospitality was of the very best I have seen...he was so kind, helpful and caring and lovely to talk with during the stay. He cares so much and wants to make sure his guests have the best experience. And wow the baked goods are incredible! This was the best mini retreat I could have imagined..I will definitely be back!

Private cottage rentals

Guest favourite
Cottage in Healdsburg
4.95 out of 5 average rating, 61 reviews

Vineyard views close to town w/ free EV charger

JillRating, 5 stars2 weeks ago
We loved spending the weekend at Mike’s Healdsburg cottage - a great place with everything we needed, central location that felt peaceful, nice outdoor space, and Mike is a super responsive and helpful host. We will gladly come back!
Top Guest favourite
Cottage in Cotati
5 out of 5 average rating, 28 reviews

Redtail Hawk Cottage | Private & Sparkling New

BethRating, 5 stars3 weeks ago
Thank you for a wonderful stay at your home. It provided a comfortable and peaceful setting for us to relax and recharge. The amenities were perfect—thoughtfully chosen and well-maintained. We especially appreciated the extra touches like the selection of snacks and coffees, which catered to a variety of tastes. Your responsiveness and attention to detail did not go unnoticed. We would definitely consider returning for a longer stay in the future!
Guest favourite
Cottage in Guerneville
4.98 out of 5 average rating, 48 reviews

2 Beds 1.5 Bath Full Kitchen Work Station Laundry

MarcusRating, 5 stars4 days ago
Dear Jessica and Jon, Thank you so much for creating such a special space at The Alchemy Tree House. We had a wonderful stay. From the moment we arrived, we felt at ease—surrounded by the redwoods, with everything so thoughtfully designed and cared for. You’ve created a place that feels both grounding and inviting, and we appreciated the attention to detail. The location was perfect for exploring—close to the Russian River, Armstrong Redwoods, and not far from the coast. But honestly, just being able to relax in the quiet, surrounded by trees, was a gift in itself. We also really appreciated how warm and responsive you were throughout our stay. It’s clear how much love you’ve poured into the place. We’d absolutely love to come back someday. Warmly, Marcus
Guest favourite
Cottage in Monte Rio
4.98 out of 5 average rating, 61 reviews

Cottage C - Comfy and Cozy 1 bed 1 bath cottage

KenRating, 5 stars2 weeks ago
Cottage C was amazing! Loved the hot tub under the redwoods! The Russian River was fun if we wanted to stay close and you can’t beat the Northern California Coast 15 minutes away!
Superhost
Cottage in Hidden Valley Lake
4.85 out of 5 average rating, 54 reviews

Windmill Cottage: A Peaceful & Private Retreat

Scott And PamRating, 5 stars1 month ago
This was our second stay at Windmill Cottage. It is an ideal size and location for visiting our son and daughter-in-law who are building a home in the area. The cottage has all the features required for an enjoyable stay. We will look forward to staying here again on our next trip to the area.
Guest favourite
Cottage in Healdsburg
4.88 out of 5 average rating, 85 reviews

Riverfront Wine Country Cottage With Views and Spa

SaraRating, 5 stars2 months ago
Edrene’s place is even more beautiful and quaint in person! Great views in the backyard, nice and quiet neighborhood, but only 10min drive from downtown.
Superhost
Cottage in Calistoga
4.93 out of 5 average rating, 29 reviews

Luxury Cottage in Downtown Calistoga - Accessible

LucyRating, 5 stars1 month ago
We arrived during a black-out of electricity. Cindy, our hosted, made us feel welcomed and assisted with genuine care of our concerns. We felt welcomed and cared for. The property was charming and it made us feel like we were truly in the country. Each cottage was detached--so no neighbors to listen through walls. Many thoughtful amenities throughout and the continental breakfast had quite a few options, including Oat Milk for those that cannot have dairy product. Great place to stay!
Superhost
Cottage in Middletown
4.85 out of 5 average rating, 27 reviews

Adorable Cottage - Walking distance to downtown

LouisRating, 5 stars8 months ago
I spent a couple of days at Harbin, Hot Springs, soaking and meditating. Shannon’s place was just a few minutes from Harbin and also walking distance to restaurants and grocery. Great quiet neighborhood.

Destinations to explore

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  3. California
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