House vacation rentals in Windsor

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Top-rated house rentals in Windsor

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Top guest favorite
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 favorite
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, 430 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 favorite
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.

Guest favorite
A cozy living room features two seating areas with a gray sofa and a beige armchair. A coffee table sits in front of them, and a flat-screen TV is positioned across the room, complemented by a decorative artwork and large windows allowing natural light.
Home in Santa Rosa
4.85 out of 5 average rating, 213 reviews

Spacious 3BD/2BA, ideal for families!

Located in a quiet residential neighborhood in Santa Rosa, this spacious single level house is in the heart of California's Wine Country. With 3 bedrooms, 2 bathrooms, an open-plan living room and fully equipped kitchen there is plenty of room to cater for friends and family. The property has parking for two cars and outdoor seating to enjoy the great California weather on the new patio. Enjoy a local wine tour, explore a Giant Redwood forest or explore the stunning coastline at your feet.

Top guest favorite
An inviting living area features a large black sectional sofa complemented by a wooden coffee table atop a light area rug. Natural light streams through large windows adorned with sheer curtains, illuminating traditional wood accents and hardwood floors.
Home in Santa Rosa
4.96 out of 5 average rating, 649 reviews

Craftsman 2 blocks from Russian River Brewery!

Tastefully updated craftsman w/ traditional wood accents & original hardwood floors. Perfect for a weekend getaway, or business trip, just 2 blocks from the Russian river brewery & down town there is no better location for food and an authentic wine country experience. City of SR STR requires max occupancy: 6 max add. daytime guests 3 quiet hours must be observed between 9 p.m. and 8 a.m. no outdoor amplified sound is allowed. 3 off street parking spaces, STR Permit number #SVR25-145

Guest favorite
A modern living area showcases a comfortable gray sectional sofa and two accent chairs. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. Soft lighting is provided by a ceiling fixture and table lamps, enhancing the inviting atmosphere.
Home in Healdsburg
4.91 out of 5 average rating, 134 reviews

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or close friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

Top guest favorite
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, 105 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 favorite
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, 684 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 favorite
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, 179 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 favorite
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.

Guest favorite
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, 192 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 favorite
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, 433 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.

Popular amenities for Windsor house rentals

When is the best time to visit Windsor?

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Quick stats about house rentals in Windsor

  • Total vacation rentals

    Explore 60 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 3,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & 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

  • Wi-Fi availability

    60 of Windsor vacation rentals include wi-fi 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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