Property Tag: 30+ Day Stays


Properties Available 31 properties available
**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
Hot HOT 29
Healdsburg Plaza Gem Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.8 (48)
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
Hot HOT 32
Lux Wine Country Oasis with Hot Tub Wine Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (32)
Escape to a dreamy 4-bedroom farmhouse nestled among Sonoma’s rolling vineyards and quiet country roads. From sipping wine by the fire pit to watching sunsets over Mount St. Helena, Moore Family Farmhouse blends rustic charm with modern comfort — an inviting Wine Country retreat for families, friends, and wine lovers alike.What makes this home espe
Hot HOT 24
Moore Family Farmhouse Wine Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.7 (27)
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
Hot HOT 22
Vista Retreat Private Studio Hot Tub Tastings
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (86)
Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country.As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This
Hot HOT 35
Eastside Eden Pool Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.6 (5)
Hot tub is in! (Pictures to come)Searching for that ideal sanctuary space that offers quiet respite for the weary soul? Look no further than this Sebastopol home which is perfect for family gatherings, couples getaways, artist/writing escapes, remote workers, and small groups seeking a comfortable, well-appointed retreat in the coveted town of Seba
Hot HOT 23
Elks Landing Hot Tub and Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (11)
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
Hot HOT 17
Heart of Healdsburg Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.5 (2)
Welcome to Eden – a rare one-acre estate tucked into the heart of Bennett Valley, where sweeping vineyard views meet effortless Wine Country living. Shaded by majestic heritage oaks and bordered by two seasonal creeks, this exclusive retreat offers three distinct residences on a single property, perfect for families, friends, or groups seeking both
Hot HOT 35
Bennett Valley Eden 3 homes with Hot Tub Tastings Included
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.8 (43)
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
Hot HOT 17
Bodega Bay Oasis Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (21)
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
Hot HOT 42
Trentadue Winery Farmstay with Pool and Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 24
Vineyard Vue Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (46)
Escape to Sanctuary on Lytton, an extraordinary 11.67-acre estate in the heart of Alexander Valley, just 7 minutes from Healdsburg Plaza. This exclusive retreat offers ultimate privacy, breathtaking mountain and valley views, and a serene bird refuge, making it ideal for family reunions, friends’ getaways, corporate retreats, or creative workshops.
Hot HOT 52
Sanctuary Estate Wine Tastings Included
House
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 18 guests
Rating 5 (4)

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