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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.

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  1. Our House Healdsburg Elegance in the Vineyards — Property 215582

    Vacation Estate rental in Healdsburg area
    • Estate
    • 6 bedrooms , sleeps 12
    • 4 bathrooms
    • downtown, rural
    • accept credit card
    Small Group Discounts 4-8 in party.
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $5700 per property per week

  2. Healdsburg Country Cabin in Beautiful Dry Creek Valley — Property 243532

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • rural
    • accept credit card
    Rates (shown in USD)
    $1113 per property per week

  3. Wine Country Modern Barn — Property 237974

    Vacation Studio rental in Healdsburg area
    • Studio
    • 1 bedroom , sleeps 2
    • rural
    • accept credit card
    Rates (shown in USD)
    $900 per property per week

  4. Villa Tranquillo -Mediterranean Resort Style Estate Pool/Spa — Property 186396

    Vacation Estate rental in Healdsburg area
    • Estate
    • 4 bedrooms , sleeps 8
    • 4 bathrooms
    • mountain, resort
    • accept credit card
    Rates (shown in USD)
    $4865 - $5565 per property per week

  5. Interlude — Property 39351

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 7
    • 2 bathrooms
    • coffee maker
    • children welcome
    Rates (shown in USD)
    $3640 - $4725 per house per week

  6. Vacation Stimulus! Kokopelli Country Alexander Valley Retreat — Property 187029

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • swimming pool
    • air-conditioning
    Rates (shown in USD)
    $2500 per property per week

  7. 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
    • accept credit card
    Rates (shown in USD)
    $2765 per property per week

  8. VACATION STIMULUS! Romantic Vineyard Villa Estate on 20 gated acres — Property 212744

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • 1 half bathroom
    • rural, village
    • accept credit card
    Rates (shown in USD)
    $3650 per property per week

  9. Firefly - Rustic Elegance in a Relaxing Riverfront Location — Property 111118

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 12
    • 2 bathrooms
    • beach, river
    • accept credit card
    Rates (shown in USD)
    $2793 - $4725 per property per week

  10. Riverwood - Beautiful Beachfront Home - Healdsburg, sleeps 6-14 — Property 117991

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 14
    • 3 bathrooms
    • river, waterfront
    • accept credit card
    Rates (shown in USD)
    $3185 - $5103 per property per week

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