Family-friendly vacation rentals in Healdsburg

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.

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

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

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 Carriage House 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 cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

Peaceful location, hot tub, fire pit, game room!

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is comfortable luxury in a spacious private cottage within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect base for your Wine Country get away. There is no stove/oven due to zoning/licensing so the cottage has a microwave, small air fryer, toaster and bbq.

Designer Cottage | Garden Oasis | Walk to Plaza

✓ Seamless indoor-outdoor living. ✓ Fully equipped kitchen. ✓ On-site EV charger. ✓ Private, architect-designed cottage for two. ✓ Just a 4-minute walk to Healdsburg Plaza. ✓ Lush, private garden. ✓ Dedicated workspace. ✓ Comfortably accommodates 2 guests. ✓ Close to world-class wineries and dining. ✓ Stylish retreat created especially for couples. ✓ Comfortable Queen Bed with Hotel pressed Sheets.

Bee Haven Cottage

This unique property is located only 2.4 miles from Healdsburg Plaza. Situated on a historic 11-acre farm with 5 acres of Zinfandel grapes. This newly renovated Studio cottage was built in 1903. This creekside cottage is fully restored in an artist's handcrafted manner. All the furnishings are of the highest quality. Enjoy the natural surroundings while soaking in the private outdoor spa.

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!