Pools


Properties Available 31 properties available
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 HOT 34
Healdsburg Homestead with Pool Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.8 (32)
Perched above Dry Creek Valley with panoramic vineyard views, this newly furnished private retreat features a pool, hot tub, bocce court, and exclusive winery tastings included with your stay.Enjoy complete privacy on a quiet country road just 15 to 20 minutes from Healdsburg Plaza.Wine Country seclusion without sacrificing access._________________
Hot HOT 38
Chateau Chemise Pool Hot Tub Wine Tastings
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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 25
Vineyard Vue Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (46)
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 HOT 38
Redwood Riverfront Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.6 (74)
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 HOT 24
Santini Farmhouse Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (60)
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 31
Moore Family Farmhouse Wine Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.7 (27)
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 22
Elks Landing Hot Tub and Tastings Included
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (11)
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 52
Trentadue Winery Farmstay with Pool and Wine Tastings Included
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 24
Fitch St Escape Wine Tastings Included
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (9)
Nestled between towering redwoods and rolling vineyards, Puccioni Paradise offers an intimate Wine Country escape for couples or solo travelers seeking tranquility and romance. Just 15 minutes from Healdsburg Plaza's renowned restaurants and tasting rooms, this peaceful sanctuary combines modern comfort with natural beauty—perfect for romantic geta
Hot HOT 24
Puccioni Paradise Wine Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 3 guests
Rating 5 (5)
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 39
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)
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
Hot HOT 28
River View Lodge Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 8 guests
Rating 4.8 (7)

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