Family-friendly holiday rentals in Windsor

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.

Wine and Golf Paradise in Windsor, CA (#1)

The WorldMark-Windsor resort is a timeshare resort located within the Russian River Valley. It is one of California's most beautiful wine regions. The name on the reservation must be the person checking in at the front desk. You must be at least 21 years old to check in. Wifi is available for an additional fee. The resort charges and collects the fee. If your check-in date is on a Friday there may be a delay in getting your room as there is a large volume of guests checking in on Fridays.

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

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!

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.

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

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.

Wine Country Cottage Escape

Hidden down a quiet private lane & surrounded by vineyards, you will feel worlds away from the hustle and bustle of every day life yet only be moments away from everything Santa Rosa, Healdsburg, and the Russian River have to offer. License #LIC24-0961 TOT#4924 all bookings are subject to 12% tot Max overnight guest: 6 Max on site vehicles:NA Max off site vehicles:0 Nighttime hours 9:00 pm -7 :00 pm must be observed No outdoor amplified sound of any kind allowed.

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.

Three-Building Healdsburg Homestead with Wine Barn

Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!