House vacation rentals in Windsor

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Top-rated house rentals in Windsor

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Guest favourite
A cozy living room features light wood flooring and natural light filtering through sheer white curtains. An upright piano is positioned against the wall, accompanied by a wooden chair and a small side table. Decorative plants enhance the serene environment.
Home in Sebastopol
4.9 out of 5 average rating, 842 reviews

Wine/Apple Country Cottage, Centrally Located

Play golden oldies on an upright piano in a home filled with antique furniture, folk art, and lots of books and games. The kitchen and bathroom also retain their vintage vibe. A drop leaf desk and 100 mbps Wi-Fi provide a comfortable working space. Come in the spring or summer to see the garden in full bloom! (Photos included here do not do it justice...) The dappled shade of a grape covered pergola is a wonderful place for lunch. The house has two bedrooms that look out on the gardens. The master bedroom has a queen bed, and the second bedroom has a double bed. There is a well-equipped kitchen and laundry room. Water in the house is delicious, purified well water. A 55" tv is in one of the bedrooms (disguised by a pull-down map). It has Roku but no cable. Enjoy lots of games and books to read, a piano in the living room and access to high speed internet and WiFi. Wander in the gardens or orchard in the back. Relax or dine under the shady grape arbor. I live in a small cottage in the back of the property. While I respect your privacy, I enjoy meeting new guests and welcome your questions. On parle francais. Se habla espanol. The house is located in apple country, outside the small town of Sebastopol. It's very easy to find in a quiet, tree-lined neighborhood across the street from a Christmas tree farm. Apple orchards and vineyards are within walking distance. The quaint town of Graton is half a mile away. It has an art gallery operated by local artists, an antique store and a variety of restaurants including the Underwood Bar and Bistro, rated as "number 4 of America's 50 Most Amazing Wine Experiences by the Food and Wine Magazine." A recent article in the local paper describes nearby Graton well: https://www.pressdemocrat.com/news/9514352-181/explore-graton-west-county-town?artslide=1 In the town of Sebastopol, there is a large variety of popular restaurants. We also have over 40 wineries, including the top rated: Merry Edwards, FEATURED IN JULY 2014 ISSUE OF SUNSET MAGAZINE and just 0.2 miles from the house! Graton Ridge Cellars, FEATURED IN JULY 2014 ISSUE OF SUNSET MAGAZINE and 0.6 miles from the house! Red Car Wine Company, 0.3 miles away. Iron Horse Vineyards also featured in July 2014 issue of Sunset Magazine and 3.6 miles from the house! Other recommended wineries in Sebastopol include: Lynmar Iron Horse Taft Street Cahill Dutton-Goldfield (one third mile from house) Scherrer Freeman Marimar. Enjoy several hiking trails close by, or drive on scenic country roads directly from the house to a variety of attractions. There is a gorgeous half-hour drive through the town of Occidental to the ocean. The Russian River Steelhead Beach is 5.6 miles away. Drive ten minutes farther to visit Armstrong Redwoods State Natural Reserve where you can walk through a towering forest of trees that are hundreds of years old. Historic Healdsburg, with its central plaza, shops, restaurants and wineries is also a scenic 25 minute drive away. The 9-hole Sebastopol Golf Course is a little over a mile away. There is a variety of grocery stores in Sebastopol. My favorite is Andy's, a fruit and vegetable stand that also carries other food. It takes 3 minutes to drive there. This area was not impacted by the fires.

Top guest favourite
A serene pool area features a sparkling blue pool surrounded by lounge chairs under palm trees. The natural landscape offers rolling hills in the background, while soft lighting from string lights enhances the tranquil atmosphere as the sun sets.
Home in Forestville
4.99 out of 5 average rating, 132 reviews

Giusti Ranch, by Vinifera Homes

“An amazing property that exceeds any descriptions that can be provided. From the grounds to the house everything is first-class” - Michael. This 19-acre family-owned working ranch is the perfect setting for your wine-country adventure. Enjoy the surrounding views, refreshing pool, hot tub, gourmet kitchen & spacious great room. Located just mins. from renowned wineries & Michelin-starred restaurants, Giusti Ranch, A Vinifera Homes Property has everything you need for a truly memorable stay!

Guest favourite
The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.
Home in Windsor
4.99 out of 5 average rating, 124 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

Top guest favourite
A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.
Home in Healdsburg
4.92 out of 5 average rating, 119 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

Top guest favourite
A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.
Home in Graton
5 out of 5 average rating, 678 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Top guest favourite
A modern kitchen features a large island with four bar stools, blending navy cabinetry with marble countertops. Bright windows illuminate the space, revealing a glimpse of the outdoor area. An elegant gold sink contrasts with stainless steel appliances and minimalist decor.
Home in Santa Rosa
4.98 out of 5 average rating, 101 reviews

Botany House Designer Home with Hot Tub

Message us on Social Media at Inspired in Sonoma for Inspiration and Tips. Discover your Wine Country sanctuary in this lush, design-forward Santa Rosa retreat. With a chef’s kitchen, a six-person hot tub, a fire pit, and Restoration Hardware furnishings, every detail is crafted for comfort and style. Perfectly located near wineries, Michelin-star dining, and redwood adventures, it’s ideal for families or friends seeking luxury and connection. Book your Santa Rosa escape today.

Top guest favourite
The kitchen features warm wooden cabinetry and an expansive central island. Stainless steel appliances include a refrigerator and microwave. Pendant lights illuminate the space, while natural light streams through a nearby window. Bar stools provide seating at the island, enhancing a functional cooking area.
Home in Santa Rosa
5 out of 5 average rating, 177 reviews

Casa de Gamay - Your Home Away From Home

Casa de Gamay is your home away from home. We've strove to include all the amenities one would need. Start with a complete kitchen with a few items ready to cook for that last minute dinner. We have the spices and staples to help you create a marvelous meal. Sit down next to our gas fireplace and watch cable TV (Comcast with a voice controlled remote), DVD player, Netflix, Hulu. Charge your car in our EV station, and then sleep in a king sized bed. Doesn't get better.

Top guest favourite
An expansive outdoor patio area features modern metal furniture and a covered dining table, inviting al fresco meals. Large sliding glass doors create a seamless flow between indoor and outdoor spaces, with a view of the surrounding natural landscape and vineyard beyond.
Home in Santa Rosa
4.97 out of 5 average rating, 127 reviews

WineCamp - Russian River Valley AVA - No Pets

The WineCamp concept is rooted in the rural ambience of working local vineyards and craft breweries. This purpose-built residence offers indoor/outdoor living at it best. Conceived as the ideal space for two adult couples, the spacious dual master suites are separated by gracious open-plan living areas that flow seamlessly through multi-panel sliding walls of glass onto the covered terrace and vineyards beyond. This wine and beer themed property is not suitable for children.

Guest favourite
An open living space seamlessly connects with an outdoor deck, featuring a dining table set for several. Natural light floods the area, highlighting wooden flooring and a cozy rug. Lush greenery can be seen in the garden area beyond the deck, creating a serene atmosphere.
Home in Healdsburg
4.94 out of 5 average rating, 188 reviews

Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place. Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax. Luxury bathroom with heated towel rack, heated floor and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

Top guest favourite
A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.
Home in Windsor
4.96 out of 5 average rating, 430 reviews

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Top guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 201 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Top guest favourite
Home in Santa Rosa
4.97 out of 5 average rating, 210 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

Welcome to Your Relaxing Getaway! My home is a comfortable, clean, and happy space—perfect for unwinding and enjoying all that Sonoma County and the Bay Area have to offer. 🌿 Spacious Backyard: Large yard with a pool (heated by the sun) 6-person hot tub (kept at 102°F) Easy parking 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal Note: Outdoor cushions/umbrellas stored late Oct to mid-May Come stay—you’ll love it! Happy House Permit #: SVR24-194

Popular amenities for Windsor house rentals

When is the best time to visit Windsor?

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Avg. price$395 CAD$374 CAD$394 CAD$401 CAD$435 CAD$429 CAD$498 CAD$492 CAD$465 CAD$482 CAD$486 CAD$421 CAD
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Quick stats about house rentals in Windsor

  • Total vacation rentals

    Explore 70 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Windsor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.9 Average rating

    Windsor stays are highly rated by guests—averaging 4.9 out of 5!

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