Vacation rentals in Windsor

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.

Redwood Treehouse Retreat - Hot tub, fire pit

Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

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.

Bucher Vineyard Studio

Experience the best that wine country has to offer with a stay in our newly remodeled studio apartment, nestled on a historic vineyard on Westside Road in the heart of the Russian River Valley. Located just 5 miles from downtown Healdsburg, you’re close to Michelin-rated restaurants, or you can cook in the fully equipped kitchen. Relax in our beautiful outdoor space or take a stroll through the scenic vineyards. Enjoy the perfect blend of tranquility & convenience at our vineyard retreat.

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.

Mediterranean Getaway with breakfast Healdsburg

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, and buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

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

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.

Windsor 2 Bed/2 Bath Condo ~ Pool ~ Hot Tub ~ Gym

**Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.

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.

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.

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!