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!
21 properties available
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
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
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.🍷 Complimentary Wine Tastings,
Ideally located right outside the Healdsburg City limits, just 2 miles from the Plaza! This recently remodeled 3 bedroom home features a large Great Room with cathedrals ceilings & picturesque gas fireplace. There are picture windows and doors throughout that bring the outside in. The home sits on 3 acres among beautiful heritage oak trees that
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 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.🍷 Complimentary Wi
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
Wake up to valley views over coffee on the deck. Spend the afternoon by the saltwater pool or hitting the ping pong table. Gather around the fire pit as the sun drops behind the hills, then head inside to a chef's kitchen built for a real group dinner. This private Sonoma estate spans three separate structures across 11 acres, giving your group bot
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
Relax and recharge at Riverbend Retreat, a warm and inviting 3-bedroom, 1.5-bath bungalow nestled in a peaceful neighborhood just 5 minutes from Healdsburg Plaza. Perfect for couples, families, or a group of friends, this home blends rustic charm with modern comfort, offering an ideal base for exploring Sonoma wine country or simply unwinding by th
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 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.🍷 Complimentary Wine Tastings, Exclu
Tell us what you're looking for and someone will contact you with available options.