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The Two of You in Healdsburg

If you’re looking for a pretty good bottle of wine, it’s no secret that Sonoma County is a smart place to start. In addition to finding a fine pour you’ll find a few other things, too, including a fabulous all-around vacation spot.


Wine sets the tone for an experience in Healdsburg but by no means does it dominate. In addition to strolling through the orchards, farms and vineyards, you’ll also find a lively downtown scene ready to sate all cultural, culinary and creative urges. Along the Russian River is a romantic vacation waiting to happen, so clear a few days from your schedule, grab your favorite person, and see what develops.


Form a solid foundation for your trip by reserving a Vacation Rental in Healdsburg. These properties are everything they should be: elegant, cozy, budget-friendly and warm. Depending on your taste and expectations you’re sure to find just what you’re looking for – most notably, plenty of privacy and a little peace and quiet.


Downtown Healdsburg has an artsy side you’ll quickly grow fond of. A Jazz Festival each June, a healthy scene of local painters, sculptors and jewelry designers, farmers markets, fine restaurants and a few surprises in between will make each journey to the city center a treat. Go back and forth between the peaceful countryside and the heart of Healdsburg in order to ensure that you don’t miss a thing.


California Wine Country could change your definition of a vacation forever. Scout out your favorite spots because a return visit is most definitely in the cards…maybe next time you’ll even bring the kids. Or not.

  1. Healdsburg Farmhouse in Private Vineyard-4 minute drive to Plaza — Property 103437

    Vacation Farmhouse rental in Healdsburg area
    • Farmhouse
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • rural, village
    • garden
    Rates (shown in USD)
    $2800 per property per week
  2. 2 Bed, 2 Bath Wine Country Paradise, Spa, Views, Lrg Deck — Property 180577

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, rural
    • garden
    Rates (shown in USD)
    $1200 - $1550 per property per week
  3. Northwoods - A Favorite Riverfront Getaway in Healdsburg w/hot tub, dock, kayaks — Property 212356

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • river, waterfront
    • pool
    Rates (shown in USD)
    $1673 - $2065 per property per week
  4. Gorgeous Healdsburg Wine Country View Estate — Property 232350

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • mountain
    • pool
    Rates (shown in USD)
    $6000 per property per week
  5. 3 BR Arts and Craftsman Bungalow in World Class Vineyard — Property 240934

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • rural
    • pool
    Rates (shown in USD)
    $2765 per property per week
  6. Emma's Cottage - Perfect for Wine Lovers! — Property 240936

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • town
    • jacuzzi
    Rates (shown in USD)
  7. Blue Heron House - Riverfront Home w/ Spa, Views & Beach — Property 224776

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • beach, river
    • jacuzzi
    Rates (shown in USD)
    $3000 per property per week
  8. Holiday Magic! Luxury Tuscan Vineyard Villa- Secluded & Serene — Property 167873

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • rural, town
    • jacuzzi
    Rates (shown in USD)
    $4865 per property per week
  9. VILLA MODERNA
    The Ultimate Contemporary Wine Country View Estate — Property 201489

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 4 bathrooms
    • 1 half bathroom
    • rural, town
    • jacuzzi
    Rates (shown in USD)
    $7500 per property per week
  10. Holiday Deals!!! Winelover's 1922 Farmhouse in world class Merlot Vineyard — Property 190656

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • rural, town
    • garden
    Rates (shown in USD)
    $3465 per property per week

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