Healdsburg Plaza
36 properties available
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
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
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
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.The home blends classic Wine Country charm with thoughtful, curated interiors. Original hardwood floors run throughout, and the light-filled living room features a cozy firepla
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
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
Escape to Sanctuary on Lytton, an extraordinary 11.67-acre estate in the heart of Alexander Valley, just 7 minutes from Healdsburg Plaza. This exclusive retreat offers ultimate privacy, breathtaking mountain and valley views, and a serene bird refuge, making it ideal for family reunions, friends’ getaways, corporate retreats, or creative workshops.
Perched above Dry Creek Valley with panoramic vineyard views, this newly furnished private retreat features a pool, hot tub, bocce court, and exclusive winery tastings included with your stay.Enjoy complete privacy on a quiet country road just 15 to 20 minutes from Healdsburg Plaza.Wine Country seclusion without sacrificing access._________________
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
Welcome to your extended stay retreat in the heart of wine country! This beautifully furnished 3-bedroom, 2-bath home is tucked away on quiet street in Healdsburg and is an easy walk to the renowned Plaza with its local restaurants, tasting rooms, boutiques, and cafés.Designed for comfortable 30+ day stays, this inviting home combines the charm of
Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of
Wake up to ocean views, vaulted ceilings, and salty coastal air—just steps from the sand.Bodega Bay Oasis is a light-filled, 3-bedroom, 3-bath coastal retreat with panoramic ocean views, two private decks, a fire pit, and three king beds, offering the perfect blend of comfort, scenery, and location. Just a short walk to Portuguese Beach and moments
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