Property Tag: Healdsburg Plaza


Properties Available 31 properties available
Tucked just eight minutes from downtown Healdsburg, this Luxurious Wine Country retreat invites you to slow down, reconnect, and savor the best of Sonoma County. Wake to peaceful vineyard views, spend sun-filled days exploring nearby wineries, and return home to evenings spent soaking in the hot tub, gathering around the fire pit, or laughing over
Hot HOT 32
Lux Wine Country Oasis with Hot Tub Wine Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (32)
Escape to Santini, an exclusive farmhouse estate in the heart of Dry Creek Valley, just 8 miles from Healdsburg Plaza. Surrounded by world-class vineyards, this newly built home combines seclusion, comfort, and modern luxury, making it perfect for families, couples, or groups of friends seeking a Wine Country retreat.This home offers a perfect blen
Hot HOT 30
Santini Farmhouse Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (60)
Experience the best of Healdsburg living at Heart of Healdsburg, a charming 2-bedroom Tuscan-style cottage just steps from the vibrant Healdsburg Plaza. This bright and airy retreat combines wine country charm with modern comforts, offering an ideal base for couples, families, or friends seeking an unforgettable Sonoma getaway.Wake up to morning su
Hot HOT 17
Heart of Healdsburg Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.5 (2)
Escape to a dreamy 4-bedroom farmhouse nestled among Sonoma’s rolling vineyards and quiet country roads. From sipping wine by the fire pit to watching sunsets over Mount St. Helena, Moore Family Farmhouse blends rustic charm with modern comfort — an inviting Wine Country retreat for families, friends, and wine lovers alike.What makes this home espe
Hot HOT 24
Moore Family Farmhouse Wine Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.7 (27)
Serenity on Dragonfly is a charming 3-bedroom country home nestled in the heart of Wine Country, just minutes from the vibrant Healdsburg Plaza with its top-rated restaurants and renowned tasting rooms. Merriam and Limerick Lane wineries are within walking distance, offering a truly immersive wine country experience.Beyond the stunning home and loc
Hot HOT 25
Serenity with Hot Tub and Wine Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
**Hot Tub is in!**Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly, standalone retreat blends vintage charm with thoughtful modern updates, including Wi-Fi, air conditioning, a dedicated workspace, and a private entrance.Now featuring a **b
Hot HOT 29
Healdsburg Plaza Gem Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.8 (48)
Retreat to the exquisite Heron House, a riverside haven where the towering Redwoods meet the flowing beauty of the Russian River. This special riverfront home offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain’s wooded knoll, the setting feels wonderfully secluded—yet ne
Hot HOT 29
Heron House Hot Tub and Wine Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (35)
Slow down, unplug, and breathe in the beauty of riverfront living at Rivers Breeze, a charming 2-bedroom, 1-bath main house with a private 1-bedroom, 1-bath lower-level suite, nestled along a peaceful stretch of the Russian River, just minutes from downtown Healdsburg and nearby wedding venues. Perfect for couples, families, or friends, this retrea
Hot HOT 20
Rivers Breeze Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (24)
Escape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine
Hot HOT 25
Private Vineyard Haven with Pool Hot Tub and Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (74)
Escape to Valley Vista, a newly renovated hillside retreat nestled among towering redwoods—just 1 mile from the Russian River and downtown Guerneville. Ideal for couples, families, or remote work, this private home offers cozy lodge charm, modern comforts, and peaceful outdoor living.Sleeps 6-8 | Main House + Private Studio (included)Your reservati
Hot HOT 22
Vista Retreat Private Studio Hot Tub Tastings
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (86)
Nestled between towering redwoods and rolling vineyards, Puccioni Paradise offers an intimate Wine Country escape for couples or solo travelers seeking tranquility and romance. Just 15 minutes from Healdsburg Plaza's renowned restaurants and tasting rooms, this peaceful sanctuary combines modern comfort with natural beauty—perfect for romantic geta
Hot HOT 34
Puccioni Paradise Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 3 guests
Rating 5 (5)
Welcome to Healdsburg Homestead!In the heart of Sonoma County’s Dry Creek Valley, this peaceful farmhouse sits along a quiet country road, surrounded by vineyards, gardens, and the gentle sound of a seasonal creek. Though it feels worlds away, you’re just 5 minutes from downtown Healdsburg’s tasting rooms, boutiques, and acclaimed restaurants.Wake
Hot HOT 32
Healdsburg Homestead with Pool Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.8 (32)

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