House vacation rentals in Windsor

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.

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.

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.

4.99 out of 5 average rating, 128 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.

A spacious living room features two comfortable sofas, a circular coffee table, and a fireplace. Soft lighting enhances the welcoming atmosphere. The adjoining dining area, visible in the background, includes a large wooden dining table surrounded by chairs, while natural light streams through the window.

4.94 out of 5 average rating, 202 reviews

Back Yard Escape: Mins to Wineries & Downtown

Welcome to your home away from home! Tucked away in the peaceful Rincon Valley neighborhood of East Santa Rosa, our cozy retreat offers a perfect escape from the everyday. Surrounded by lush, manicured landscaping, it’s the ideal spot to unwind and recharge. With convenient access to world-renowned wineries and vibrant craft breweries! Whether you're here to sip, explore, visit loved ones, or work, our home serves as the perfect base for your adventure. So go ahead, get comfy, and stay awhile!

A spacious living area is illuminated by natural light from large windows. Plush sofas are arranged around a coffee table, while a fireplace adds warmth. A wall-mounted TV is positioned for easy viewing. A sliding door leads to an outdoor space with seating.

4.94 out of 5 average rating, 288 reviews

Russian River Brew-cation · Wine Tasting Retreat

Welcome to the Russian River Brewhouse in the heart of Wine Country. Enjoy a space made for comfort and connection, with evenings best spent gathered around the fireplace. You can arrange a private wine tasting in the home, where a tasting experience is brought directly to you. No driving, no reservations, just a relaxed and memorable way to enjoy Wine Country from the comfort of your rental. Your reservation includes tastings at CAST Wines, Christopher Creek Winery, and Ramazzotti Wines.

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.

4.91 out of 5 average rating, 136 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

The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.

4.97 out of 5 average rating, 214 reviews

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

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.

4.92 out of 5 average rating, 121 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.

A well-appointed bedroom features a spacious bed with a light-colored upholstered headboard, draped in soft linens and a textured throw. Two nightstands flank the bed, each with a lamp and decorative items. Large windows allow natural light to illuminate the room, while soft curtains frame the view.

4.93 out of 5 average rating, 103 reviews

Centrally Located Modern Wine Country Home

Your wine country retreat awaits you. This gorgeous home features a new modern kitchen, outdoor seating area, washer and dryer, free WiFi and parking. This home is conveniently located in the heart of wine country minutes away from Sonoma wineries, breweries, Sonoma County Airport, downtown Santa Rosa, downtown Sebastopol and great dinning. Due to COVID we clean and sanitize the house thoroughly before and after each stay. Welcome to your home away from home!! Your concierge Ana

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.

4.96 out of 5 average rating, 435 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.

A spacious dining area features a rustic wooden table set for eight, surrounded by leather-tacked chairs. Nearby, a well-equipped kitchen is visible, showcasing wooden cabinetry and modern appliances. Natural light fills the room, complemented by greenery from potted plants in the background.

4.82 out of 5 average rating, 147 reviews

Healdsburg Winemaker’s Wine Country Gem

Welcome to our 6-bedroom retreat, owned by a passionate Healdsburg winemaker, located in the heart of Windsor. This home is the perfect getaway for families, groups, or wine lovers looking to immerse themselves in the charm of Wine Country. Inside, each bedroom offering crisp linens, plush pillows, and soft lighting for ultimate relaxation. After a day of exploring the wineries, unwind in the private hot tub, where you can soak your cares away in style.

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.

5 out of 5 average rating, 222 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!

4.82 out of 5 average rating, 127 reviews

A spacious backyard is showcased, featuring a hot tub surrounded by greenery. Comfortable patio furniture is arranged under a sunshade, with a hammock and additional seating visible. A manicured lawn extends, bordered by flowering shrubs and trees, creating a tranquil outdoor space.

Home in Roseland

Sonoma Valley Vacation Home

This home is located in the Sonoma Valley in the heart of the Wine Country. You will be minutes away from dining, shopping and wineries. The newly updated home features 3 bedrooms, 2 bathrooms plus a queen sofa sleeper in the living room. Enjoy the beautiful backyard with a Hot Tub, Fire Pit, BBQ, hammock and patio seating. The home features all amenities to make your trip perfect to Wine Country and enjoy all that it has to offer! SVR22-001 TOT:3583

Popular amenities for Windsor house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

4.95 out of 5 average rating, 525 reviews

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

4.9 out of 5 average rating, 188 reviews

The exterior of a two-story California Craftsman home is shown, featuring a gabled roof and a welcoming front porch. Green lawn and garden beds with shrubs and flowers frame the pathway leading to the entrance, emphasizing the home's charming design.

Home in Junior College

Historic 1880's Craftsman Style Home with Pool.

4.96 out of 5 average rating, 102 reviews

An aerial view reveals a modern log cabin surrounded by lush greenery, showcasing a spacious pool and inviting spa. Blue lounge chairs line the pool's edge, and the property features ample outdoor space bordered by trees, enhancing the sense of privacy.

Home in Guerneville

Modern Log Cabin w/ Pool, Spa & FP Near DT & River

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.94 out of 5 average rating, 160 reviews

Wine Country | Pool & Spa | Park Views | Fast WiFi

The living room features a muted green accent wall and a large flat-screen TV mounted above a dark wooden sideboard. A gray sofa and two yellow accent chairs are positioned around a wooden coffee table, which is topped with magazines. Natural light filters through plantation shutters.

4.93 out of 5 average rating, 273 reviews

Eclectic Hideaway with Backyard Pool & Hot Tub

Two white Adirondack chairs are positioned next to a heated swimming pool, surrounded by lush greenery. The clear blue water reflects the bright sky, while lounge chairs are positioned nearby. The serene atmosphere invites relaxation and enjoyment in the outdoor space.

4.88 out of 5 average rating, 320 reviews

*Heated* Swimming Pool Retreat Near Sonoma Square

4.91 out of 5 average rating, 121 reviews

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

Home in Sebastopol

Luxury home (+ pool house) with views, pool & spa

Home in Montgomery Village

A hot tub bubbles gently, positioned next to a large swimming pool. Lush greenery surrounds the area, complemented by a vibrant sky with hues of orange and pink. A lounge chair and a sun umbrella are visible in the background, enhancing the outdoor relaxation space.

4.87 out of 5 average rating, 247 reviews

Cozy Home w/ Hot Tub/Pool- near Shops, Wine, Food

Weekly house rentals

The exterior of the modern home is displayed, showcasing a two-story structure with neutral grey siding and large windows. Pathways lined with low-maintenance landscaping lead to the entrance, with areas of gravel and various plants adding a natural touch. A wooden fence encloses the backyard.

4.99 out of 5 average rating, 117 reviews

Modern 4-Bedroom Retreat in Santa Rosa

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.

5 out of 5 average rating, 182 reviews

Casa de Gamay - Your Home Away From Home

A well-appointed sleeping area features a four-poster bed dressed with a floral duvet. Two bedside lamps flank the bed, providing soft lighting. A small wooden table and chair are situated to one side, with light filtering in from sheer curtains framing the window.

4.82 out of 5 average rating, 62 reviews

Adventures surround this charming 2bedroom home.

4.96 out of 5 average rating, 185 reviews

The front exterior of the house is highlighted, showcasing a well-maintained facade with green wood paneling and a geometric roofline. A driveway leads to the garage, complemented by potted plants on both sides of the entrance, creating a welcoming approach.

Home in West End

3 Bedrooms 1 Bath | Quiet Neighborhood House

A spacious retreat is nestled among greenery, featuring a stone pathway leading to the entrance. Solar panels adorn the roof, and soft lighting highlights the outdoor seating area. Surrounding gardens display a variety of plants, adding to the tranquil outdoor setting.

4.95 out of 5 average rating, 487 reviews

Zen House on 15 acres

4.95 out of 5 average rating, 149 reviews

A serene outdoor space features a circular seating area around a fire pit, with ocean views in the background as the sun sets. Lush trees provide a natural frame, while a hot tub is positioned nearby, creating an inviting atmosphere for relaxation.

Home in Bodega Bay

Ocean Front Paradise w Hot Tub&Fire Pit

A spacious living area features large windows inviting natural light and showcasing views of greenery. Comfortable sofas surround a wooden coffee table, while a dining table accommodates gatherings. A stone fireplace and modern TV are included, enhancing the home's charm and functionality.

4.83 out of 5 average rating, 42 reviews

Vintage Home in Healdsburg Wine Country

4.97 out of 5 average rating, 225 reviews

The exterior of the coastal cottage is depicted, showcasing a vibrant blue façade. The structure sits on stilts over the water, with a sturdy wooden deck leading up to it. Outdoor dining furniture and a gas grill are visible, creating a welcoming space with scenic views.

Home in Marshall

Driftwood | Private Coastal Escape w/ Unreal Views

Private house rentals

5 out of 5 average rating, 66 reviews

Casa de la Esperanza: 1890s Gem - Hot Tub - 5BD/3BA

A charming two-story house is framed by lush greenery and mature trees. A spacious deck is visible on the upper level, furnished with chairs for relaxation. The exterior features a combination of white siding and wooden accents, complemented by a clear blue sky in the background.

5 out of 5 average rating, 26 reviews

Blooming Acres, by Vinifera Homes

A bright and airy living area is showcased with high wooden ceilings and large windows offering views of the surrounding vineyards. A gas fireplace adds warmth, while a dining table is set for two. Comfortable seating is arranged nearby, enhancing the open space.

4.96 out of 5 average rating, 72 reviews

Sonoma-Napa Retreat with Vineyards Views

4.97 out of 5 average rating, 79 reviews

Wine Country Retreat • Fire Pit • 2-for-1 Tastings

4.5 out of 5 average rating, 8 reviews

Windsor Home with Sauna & Outdoor Fire Pit

4.93 out of 5 average rating, 43 reviews

Home in Sebastopol

The Wildflower Acre

An outdoor seating area is furnished with plush chairs arranged around a square fire table. A large umbrella provides shade over the space. In the background, a gazebo offers additional seating options, surrounded by wooden fencing and vibrant greenery.

4.96 out of 5 average rating, 81 reviews

Heart of Wine Country, Cute Cottage w/Hot Tub

A lush garden area features vibrant red and white rose bushes, flourishing in well-tended beds. The natural greenery is complemented by flurries of blossoms, creating an inviting outdoor space. Soft sunlight casts gentle shadows on the manicured grass, enhancing the serene atmosphere.