Property Category: Healdsburg
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 WC Lodging today!
21 properties available
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
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
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
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
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
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
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
**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 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
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
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
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