Family-friendly vacation rentals in Healdsburg

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

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. 🌺🙏 🌺

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!

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.

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

Updated Russian River Cabin (beach/river access!)

Escape to wine, water, nature, and cozy cabin comfort that's a short trip from SF (75 min) and only minutes to charming Healdsburg and Dry Creek Valley wineries. Right on the Russian River, our cabin is a great getaway for wine tasting, river fun (beach, canoe/kayak/SUPs), and Healdsburg (9 min). Built in 1949, we've kept the cabin's rustic charm (the antlers and the moose mount came with the place!), but updated it with modern design and conveniences. Perfect for couples or a family.

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

Country Barn in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the "barn" is a modern/rustic country-correct cottage. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Property rental supports Farm Sanctuary on site of rescue goats, horses, and one heifer named Francis.

Downtown Healdsburg Nest

You can't get any closer to all that Healdsburg has to offer. Just two blocks from the charming Plaza, this fully furnished, upstairs 2 bdr apartment has everything you need for a quick trip to Wine Country or longer-term stay. High-speed internet and all the comforts of home. Steps away from world-class restaurants, tasting rooms, shops, galleries, and music venues.

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!

Dry Creek Valley Cottage

We live in a beautiful rural country setting but we are only a 5-7 minute easy drive into downtown Healdsburg where all the lovely shops, wineries and restaurants are. We invite you to enjoy our lovely garden and taste all the wonderful fruit when it is in season. We have apple, pear, peach, plum, pomegranate, persimmon and citrus trees.

Wake Up in Your Own Private Vineyard - Healdsburg

Unwind at Homefire Sonoma's Winery and Vineyard estate just minutes from Healdsburg Plaza. This 3-bedroom, 2-bath contemporary home sits on 10 serene acres with a 2-acre vineyard, open-plan design, and a fully equipped chef’s kitchen. * If you have 5-star reviews, reach out for possible discount after booking.