Healdsburg Vacation Rentals
Welcome to Healdsburg, a jewel in the heart of Sonoma County wine country. Our curated collection of Wine Country homes—ranging from modern retreats to charming cottages and rustic farmhouses—offers the perfect blend of comfort and elegance.
Whether you’re planning a romantic escape, a family trip, or a getaway with friends, each property provides spacious living areas, gourmet kitchens, cozy bedrooms, and beautiful outdoor spaces. Many homes feature gardens, patios, and stunning vineyard or countryside views.
Browse our selection and book your ideal Healdsburg getaway with Lienna Collective today!
22 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
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
Just 2 Blocks from Healdsburg Plaza – Step into Wine Country elegance at Heavenly Hideaway, a thoughtfully remodeled historic home that puts you at the heart of Healdsburg's culinary and wine scene. Walk to award-winning restaurants, boutique shopping, and premier tasting rooms, then retreat to your private sanctuary for relaxation and connection.B
**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 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
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
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
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 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
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
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
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
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