House holiday 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, 845 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
The exterior of a charming cottage is framed by lush greenery and features a welcoming entrance with wooden doors. A stone pathway leads to the home, which is complemented by vibrant foliage and a pergola adorned with vines.
Home in Healdsburg
4.96 out of 5 average rating, 479 reviews

Dry Creek Valley Cottage

Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.

Top Guest favourite
A view of the open living area reveals a cozy sofa adorned with colorful cushions. A wooden dining table is situated nearby, accompanied by simple wooden chairs. A large artwork of sunflowers adds a touch of character, while a decorative coffee table holds potted plants and flowers.
Home in Sebastopol
4.96 out of 5 average rating, 428 reviews

Sebastopol Guest House

Let the sun shine in! Serene, modern, open floor plan with skylights, heat, A.C. full kitchen and bath and a private patio covered by a grape arbor. The Guest House is on a quiet 'country-like' road downtown, A short stroll to the Barlow, Zagat-rated restaurants, galleries, farmers markets and boutiques. Gorgeous wineries are 10 minutes away. You'll find our extensive guide book inside that we created to share our love of the area with you. We only host non-smokers and we'll meet you at check-in

Top 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, 125 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 warm living space features wooden paneling and natural light from large windows. A comfortable chair sits beside a small wooden table, and a piano is positioned nearby. Decorative plants hang from the ceiling, complemented by a cozy fireplace and a bookshelf in the background.
Home in Forestville
4.96 out of 5 average rating, 296 reviews

Forest Cozy Home

My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

Guest favourite
A spacious living area is designed for relaxation, featuring a comfortable light-colored sofa with decorative throw pillows. A large window allows natural light to fill the space, highlighting the modern décor. A stylish coffee table rests in front of the seating, complemented by a vibrant area rug.
Home in Santa Rosa
4.93 out of 5 average rating, 194 reviews

Wine Country Adventure Fun for Families & Friends

Located in Santa Rosa, this home is the perfect retreat for families, friends, and anyone looking to relax and enjoy the area. Just one block away, a fantastic new park features a playground for kids and a spacious dog park perfect for outdoor fun. Enjoy a game of billiards, unwind in the garage-turned-game room, or relax in the inviting living space. Step outside to the patio seating area and BBQ grill—ideal for dining under the stars and making unforgettable memories. SVR24-154 Permit 2024

Top Guest favourite
Home in Santa Rosa
4.98 out of 5 average rating, 103 reviews

Botany House Designer Home with Hot Tub

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 escape today. We are pet-friendly. Message us on Social Media at Inspired in Sonoma for Inspiration and Tips.

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, 682 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

Guest favourite
A dining area features a simple wooden table surrounded by four matching chairs. Natural light filters through the window, enhancing the light-colored walls and warm wooden floor. A ceiling fan is positioned above, providing a cool breeze in the space.
Home in Santa Rosa
4.94 out of 5 average rating, 166 reviews

West End Neighborhood Cottage

ID Tax 3099 1 bedroom cottage with a victorian-style interior tucked away with a quiet, shared yard and picnic table. Enjoy staying walking distance from historic Downtown where you'll find numerous small shops, microbreweries, bars, restaurants, gardens, book stores, coffee and local events. Blocks from multiple modes of public transportation makes this location perfect if you want to venture farther and explore the diverse landscapes of Sonoma County. Quiet Hours 9PM to 7AM

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, 128 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.

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, 432 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, 209 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!

Popular amenities for Windsor house rentals

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Avg. price$421 AUD$398 AUD$419 AUD$427 AUD$463 AUD$457 AUD$530 AUD$524 AUD$495 AUD$513 AUD$518 AUD$448 AUD
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Quick stats about house rentals in Windsor

  • Total holiday rentals

    Explore 70 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $45 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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