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!
33 properties available
Perched on a private ridge above Clearlake, Jago Bay Cottage offers sweeping views of California’s largest natural freshwater lake, Mt. Konocti, and 14 acres of thriving Cabernet Sauvignon vineyards. This fully gated estate provides a serene, secluded retreat—perfect for relaxing, reconnecting, and enjoying Lake County’s natural beauty.The 3-bedroo
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
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 the heart of California Wine Country at this stunning 4-bedroom, 2-bath Calistoga vacation rental. Surrounded by rolling vineyards and framed by picturesque mountain views, this private retreat offers the perfect blend of relaxation and modern comfort. Whether you’re here for a romantic getaway, wine tasting adventure, or family vacation,
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 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
Escape to Valley Vista, a newly renovated hillside retreat nestled among towering redwoods—just 1 mile from the Russian River and downtown Guerneville. Ideal for couples, families, or remote work, this private home offers cozy lodge charm, modern comforts, and peaceful outdoor living.Sleeps 6-8 | Main House + Private Studio (included)Your reservati
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 at Merriam Vineyards and Orsi Family Vineyards.Your Wine Country RetreatWhere urban sophistication meets wine country charm, Vine
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
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
**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
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
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