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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. Pension du Vigneron
    Healdsburg Pension Amongst the Vines — Property 160642

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • lake, rural
    • internet access
    Rates (shown in USD)
    $1270 per property per week

  2. Riovino - Retro Contemporary in Healdsburg — Property 205026

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • river, village
    • internet access
    Rates (shown in USD)
    $1200 per property per week

  3. Secluded Cottage in the Oaks — Property 213338

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • pets considered
    • air-conditioning
    Rates (shown in USD)

  4. The Loft
    Bright, Sunny and Spacious! — Property 251146

    Vacation Townhome rental in Healdsburg area
    • Townhome
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • downtown, lake
    • balcony
    Rates (shown in USD)
    $1000 - $1200 per property per week

  5. Downtown Healdsburg Retreat- Walk to Square- 2 BR/1 BA — Property 224233

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • downtown, river
    • air-conditioning
    Rates (shown in USD)
    $1200 per property per week

  6. Redwood Cottage — Property 39359

    Vacation House rental in Healdsburg area
    • House
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • children welcome
    • pets not allowed
    Rates (shown in USD)
    $875 - $1050 per house per week

  7. Wine Country Cottage — Property 39355

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 6
    • 1 bathroom
    • children welcome
    • pets not allowed
    Rates (shown in USD)
    $1650 per house per week

  8. Mill Creek Cottage — Property 97116

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • coffee maker
    • children welcome
    Rates (shown in USD)
    $1113 - $1477 per cottage per week

  9. The Mouse House: the most romantic, luxurious setting in the CA Wine Country — Property 235598

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • rural
    • daily maid service
    Rates (shown in USD)
    $3800 per property per week

  10. Charming Winemaker's Cottage with spectacular views and private outdoor hot tub — Property 234626

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • rural
    • garden
    Rates (shown in USD)
    $2500 per property per week

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