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!
20 properties available
THE SPACEWalk to the historic Healdsburg Plaza from this modern single-level farmhouse. Vineyard Vue features 2 king en-suites, a chef’s kitchen, a wraparound porch, and vineyard vistas. Enjoy complimentary wine tastings.Your Wine Country RetreatWhere urban sophistication meets wine country charm, Vineyard Vue is a beautifully remodeled farmhouse j
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
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
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 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
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 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
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
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
Step into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting.Blending modern design with historic charm, this bright, op
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
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
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