Healdsburg Plaza
36 properties available
Thoughtfully updated from top to bottom with all-new modern decor and high-end furnishings, this estate balances luxury with country comfort.• The Great Room: A spectacular open-concept kitchen and living area featuring soaring ceilings, a premium Thermador range, and a massive wall of windows framing panoramic vineyard views.• Primary Suite: A pri
**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
Welcome to this beautifully maintained bungalow-style home on Plaza Street — one of Healdsburg’s most coveted addresses, just a short stroll from the iconic Healdsburg Plaza. This thoughtfully preserved home blends classic Wine Country charm with curated, elevated interiors designed for comfort, style, and ease.Original hardwood floors run througho
Welcome to our stunning Barrel House nestled in the dry creek valley, the very heart of tranquility! This extraordinary getaway offers the perfect blend of relaxation and luxury, with a range of incredible amenities designed to make your stay truly unforgettable.
Situated on 2 acres, step into the enchanting Barrel House gardens where you will be
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
Tucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country e
Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country.As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This
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
Escape to Your Private Vineyard EstateJust steps from Trentadue Winery, this single-level retreat offers the ultimate Wine Country getaway. Surrounded by sweeping vineyard views and open Sonoma skies, enjoy relaxed luxury with a private pool, spacious interiors, and complimentary tastings at several renowned wineries. Ideal for couples, families, o
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
Escape to Redwood River House, a beautifully updated 2-bedroom, 1-bathroom riverfront cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Thoughtfully designed for couples, small families, or friends, this inviting Wine Country retreat pairs peaceful river views and mountain scenery with modern comforts and easy access to town
Welcome to your own slice of Wine Country magic. Just minutes from downtown Healdsburg, this private retreat is all about easy living, beautiful views, and time well spent—whether you're here to celebrate, reconnect, or simply slow down and soak it all in.Designed with groups in mind, your reservation includes both the main house and a separate one
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