Holiday rentals in Windsor

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.

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

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.

The Sonoma Spyglass | Incredible Views + Sauna

🏵️ Featured as one of “California’s Most Wishlisted Airbnbs!” 🏵️ 🌈 Come enjoy deep rest, romance & rejuvenation! ❤️ 🌺 Our Sonoma Spyglass is a gorgeous retreat, designed and built by Artistree Home, seamlessly blending sustainability with a deep connection to nature. 🍇 Tucked in the heart of Sonoma’s wine country, the space offers access to nearby walks and local wineries. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay. 🌺🙏 🌺

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.

Bucher Vineyard Studio

Experience wine country the way it's meant to be — from the inside. Our renovated studio sits on the Bucher family vineyard on Westside Road, in the heart of the Russian River Valley. You're not just near wine country, you're living in it, surrounded by the Pinot Noir vines we tend ourselves. Just 5 miles from Healdsburg Square, you're a short drive from Michelin-rated restaurants, world-class tasting rooms, and everything the valley has to offer — then come home to the quiet of the vineyard.

Botany House Designer Home with Hot Tub

Property is managed by Inspired in Sonoma 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 and look forward to hosting you.

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

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!

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

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.