Apartments and Airbnb in Healdsburg

Where to look for an Airbnb in Healdsburg

Downtown Healdsburg

Downtown Healdsburg is the beating heart of the city, filled with upscale tasting rooms, art galleries, and farm-to-table restaurants. Staying in an Airbnb in Healdsburg in this neighborhood means walking distance to the lively Healdsburg Plaza, where visitors will find concerts, cafes, and weekend farmers markets. Vacation rentals in Healdsburg in this area include loft apartments and charming historic homes, offering both comfort and convenience. This area suits travelers who enjoy a vibrant, walkable environment full of culinary and cultural gems.

Dry Creek Valley

Just outside the city center, Dry Creek Valley is ideal for those who want a peaceful escape among vineyards and rolling hills. This area is known for its world-class Zinfandel and provides stunning vistas at every turn. Vacation rentals in Healdsburg in this area often include rustic cottages and luxury homes with vineyard views. Travelers seeking to explore wineries like Ferrari-Carano and enjoy outdoor activities such as biking and picnicking will find this location especially appealing.

Russian River Area

The Russian River Area provides a tranquil atmosphere perfect for outdoor enthusiasts and lovers of water activities. Vacation rentals in Healdsburg in this neighborhood often sit close to riverbanks, offering serene views and easy access to kayaking or paddleboarding. This area suits families or couples wanting a quiet setting surrounded by nature. Visitors will enjoy the proximity to Healdsburg Memorial Beach and scenic walking trails.

Fitch Mountain

Overlooking the town, Fitch Mountain features secluded vacation homes in Healdsburg nestled in the woods, many with panoramic valley views. This neighborhood is popular with hikers and nature lovers who enjoy the mountain's quiet trails and forested surroundings. Staying in an Airbnb in Healdsburg here means waking up to birdsong and enjoying ample space to relax away from urban life. The area remains close enough to downtown for easy access to restaurants and shops.

Westside Road

Lined with prestigious vineyards and picturesque views, Westside Road is a perfect choice for wine lovers looking for an upscale stay. Vacation rentals in Healdsburg in this area range from modern estates to cozy bungalows surrounded by vines. Guests staying here will enjoy direct access to some of Sonoma’s most celebrated wineries, including Rochioli and Williams Selyem. The peaceful rural setting combined with luxury amenities draws discerning travelers seeking elegance and nature.

What to do if you spend a vacation in Healdsburg

Healdsburg Plaza

At the center of town, Healdsburg Plaza offers a picturesque square surrounded by boutique shops, restaurants, and tasting rooms. This is a wonderful place to begin any visit, whether enjoying a morning coffee or an evening glass of wine. Live music and regular community events bring energy to the plaza throughout the year. Visitors will appreciate the relaxed charm and welcoming atmosphere that defines this central space.

Ferrari-Carano Vineyards and Winery

Known for its breathtaking gardens and high-quality wines, Ferrari-Carano is a must-see in Dry Creek Valley. Guests can take guided vineyard tours, enjoy tastings of celebrated varietals, and explore the elegant Italian-style architecture. The estate’s terrace overlooks the valley and provides a lovely setting for afternoon wine sipping. This vineyard ranks among the top destinations for wine enthusiasts exploring the area.

Healdsburg Museum and Historical Society

To learn more about the area's past, the Healdsburg Museum offers exhibits on local history and culture. Visitors will find displays on Native American heritage, winemaking traditions, and the agricultural evolution of Sonoma County. The museum resides in a beautifully preserved Carnegie Library from 1910. Exploring this site enhances any visit with thoughtful historical insight and context.

Russian River Adventures

For active travelers, Russian River Adventures offers kayak and canoe rentals to explore the scenic waterways. Participants can glide past vineyards, beaches, and lush riverbanks on beginner-friendly routes. This excursion provides an ideal mix of nature and relaxation. Guests will enjoy viewing the landscape from a unique water-level perspective during their journey.

Roche Winery

Near the Westside Road area, Roche Winery delivers a personalized wine tasting experience in a cozy, family-owned setting. Guests can sip wines in the peaceful garden and attend seasonal events like harvest festivals. The welcoming atmosphere makes it stand out among the larger wineries nearby. Visitors seeking an intimate outing will appreciate this quiet, charming venue.

Healdsburg Ridge Open Space Preserve

The Healdsburg Ridge Open Space Preserve features scenic trails through oak woodlands, wildflower meadows, and ridge-top viewpoints. Hikers will encounter interpretive signs that highlight local plants and animals. The preserve provides incredible photo opportunities and moments of quiet reflection. Many locals and visitors come here to enjoy peaceful trails surrounded by nature.

Jordan Vineyard & Winery

Just outside town, Jordan Vineyard & Winery combines refined wines with guided estate tours and gourmet food pairings. The experience includes strolling through manicured gardens and sampling vintages in a chateau-inspired setting. Guests will appreciate the educational and sensory-rich journey through the property. This vineyard is ideal for travelers who enjoy elegant settings and culinary depth.

SingleThread Farm-Restaurant-Inn

Near Healdsburg Plaza, SingleThread offers an exceptional dining experience blending local ingredients with Japanese culinary techniques. The restaurant, which holds three Michelin stars, presents artfully crafted tasting menus in a serene, beautifully designed space. Booking here is a highlight for food lovers seeking a world-class experience. The inn above the restaurant also offers luxury accommodations in Healdsburg for an immersive gourmet getaway.

Where to find a vacation rental near Healdsburg, California

Santa Rosa, California

Located just 30 minutes south of Healdsburg, Santa Rosa offers a vibrant mix of culture, wine, and family-friendly attractions. Guests can visit the Charles M. Schulz Museum, explore the Sonoma County Museum, or enjoy wine tasting at nearby vineyards. After a full day of exploration, unwind in a vacation rental in Santa Rosa close to downtown or the vineyards. Santa Rosa's urban comforts and cultural variety make it a dynamic base near Healdsburg’s boutique wine country charm.

Napa, California

About an hour southeast, Napa is internationally known for its prestigious wineries, luxury spas, and fine dining. Visitors can enjoy the Napa Valley Wine Train, stroll along the Oxbow Public Market, or relax in geothermal springs. You’ll find an elegant apartment in Napa offering easy access to tasting rooms and scenic drives. Napa’s upscale atmosphere and world-renowned wine scene offer a luxurious complement to Healdsburg’s rustic sophistication.

Sebastopol, California

Roughly 45 minutes southwest, Sebastopol offers a laid-back, artsy vibe surrounded by apple orchards and organic farms. Guests can explore local art galleries, shop at the Barlow Market District, or hike in Ragle Ranch Regional Park. Settle into a creative retreat in a house in Sebastopol surrounded by gardens and quirky art. Sebastopol’s quirky charm and sustainability focus provide a relaxed and creative contrast to Healdsburg’s upscale wine culture.

Sonoma, California

Just over an hour southeast, Sonoma boasts historic landmarks, a welcoming town square, and award-winning wineries. Visitors can tour Mission San Francisco Solano, enjoy local wines, or dine al fresco in the central plaza. Stay in a classic vacation rental in Sonoma near the plaza or vineyards. Sonoma’s historic elegance and laid-back hospitality make it an ideal match for a wine-focused getaway from Healdsburg.

Calistoga, California

Located about an hour northeast, Calistoga is famous for its natural hot springs, mud baths, and charming small-town feel. Travelers can visit Castello di Amorosa, a medieval-style winery, or soak in the town’s historic geothermal spas. Enjoy a restful stay in a house in Calistoga with spa access and mountain views. Calistoga’s wellness-focused offerings and natural beauty make it a rejuvenating escape near Healdsburg.