House vacation rentals in Windsor

Find and book unique houses on Airbnb

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 G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,480 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

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 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!

Top-rated house rentals in Windsor

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
An open-concept kitchen and dining area features a large wooden dining table and modern kitchen appliances. A spacious island with bar seating is included, and the bi-fold patio doors lead to a deck with lounge seating surrounded by greenery.
Home in Forestville
4.96 out of 5 average rating, 105 reviews

Russian River Luxury Escape | Private Hot Tub

Indulge in luxury at your new modern style home. Unwind in the elegant, open space interior with natural lighting and Forestville's scenery seeping through the windows. Craft culinary creations in the fully stocked kitchen with a spacious island, and relax on the large backyard deck or hot tub. Stay connected with fast Wi-Fi, the dedicated office space, and the electric car charging outlet. Conveniently located near the Russian River, enjoy your space designed for utmost comfort and tranquility.

Top guest favorite
A bright kitchen features sleek white cabinetry and a spacious island with a light marble countertop. Pendant lights hang above the island, while large windows allow natural light to fill the space. Stainless steel appliances add a modern touch to the overall design.
Home in Windsor
4.95 out of 5 average rating, 110 reviews

Gourmet Kitchen in Wine Country w/Hot Tub + Office

There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! The 14ft bifold door invites out to the beautiful spacious yard where you can relax at any of the 4 sitting areas nestled under a beautiful display of lights. Featuring a chef kitchen, an office, large yard for children & pets, spacious bedrooms, stunning master bath, hot tub, fire table, games & more. Just minutes from elite award winning wineries, craft breweries & restaurants

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, 132 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 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, 215 reviews

Wine Country Getaway | Hot Tub + Near Park

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 favorite
An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.
Home in Healdsburg
5 out of 5 average rating, 113 reviews

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

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, 138 reviews

WineCamp - Wine Country - Vineyard View Hot Tub

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 terrace with Sundance spa hot tub and vineyards beyond. This wine and beer themed property is not suitable for children.

Guest favorite
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.
Home in Santa Rosa
4.97 out of 5 average rating, 225 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!

Top guest favorite
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.
Home in Santa Rosa
4.94 out of 5 average rating, 174 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

Escape to our stylish Santa Rosa home, your perfect base for wine country! Comfortably sleeps 8 with 4 bedrooms. Relax in the private backyard oasis featuring a pool, soaking hot tub, and a cozy gas fire pit under a gazebo. Centrally located near world-class wineries, breweries, and dining. Ideal for families and friends seeking a memorable getaway in a quiet, convenient neighborhood. We are happy to help plan your trip or arrange a private wine tasting at the house. Just ask!

Guest favorite
The living room features a leather sofa and loveseat, accompanied by an end chair. A coffee table sits in the center, and a wall-mounted TV is positioned above a gas fireplace. Large windows and sliding doors provide views of the outdoor area.
Home in Santa Rosa
4.94 out of 5 average rating, 255 reviews

Winemaker's Delight: 3BD/3BA Russian River Valley

A stylish 3-bedroom vacation rental in the heart of Santa Rosa, owned by passionate winemakers and perfectly located near top Sonoma wineries, tasting rooms, restaurants, and scenic drives. Ideal for up to six guests, this beautifully designed Wine Country retreat features inviting living spaces and three thoughtfully styled bedrooms with plush linens and serene décor, creating the perfect home base for relaxing, exploring, and enjoying the best of Sonoma County.

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, 439 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 favorite
Home in Santa Rosa
4.94 out of 5 average rating, 299 reviews

Russian River Brewcation | Wine Country Stay

Welcome to Russian River Brewcation, your Wine Country retreat in Sonoma County near the renowned Russian River Valley. This inviting home is perfect for relaxed evenings, gathering with friends, and enjoying the laid-back rhythm of Wine Country living. Guests may arrange private in-home wine tastings delivered directly to the property, along with access to curated experiences at select local winery partners. Permit # SVR25-060

Top guest favorite
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, 240 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. Your perfect wine country escape awaits!

Popular amenities for Windsor house rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$55,020 GYDG$62,760 GYDG$69,036 GYDG$59,832 GYDG$64,852 GYDG$64,016 GYDG$74,266 GYDG$73,430 GYDG$69,455 GYDG$59,413 GYDG$88,911 GYDG$75,312 GYD
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor
  6. House rentals