Vacation Rentals By Owner In Healdsburg, CA

Showing 140 Of 170 Vacation Rentals

Exceptional(27)

$1508.4

/ Nightly

Private Vacation Home

Dry Creek Ranch ~ Pool, HotTub, & Game Barn!

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(2)

$645.11

/ Nightly

Private Vacation Home

Wine country retreat

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(101)

$467.7

/ Nightly

Private Vacation Home

luxuriously appointed private large guest suite in a landmark Victorian

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(2)

$555.83

/ Nightly

Private Vacation Home

Downtown Healdsburg Contemporary Home with Pool

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(168)

$827.73

/ Nightly

Private Vacation Home

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(14)

$973.8

/ Nightly

Private Vacation Home

Family-Friendly Dry Creek Valley Retreat w/Amazing Views <15 Minutes To Square

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(1)

$239.21

/ Nightly

Apartment

Luxury new studio in downtown Healdsburg with WiFi, AC, Poolhouse/Fitness Center

Healdsburg, California, United States

Bath

Sleeps

Exceptional(7)

$283.5

/ Nightly

Apartment

The Roost - Sun Room

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(52)

$128.18

/ Nightly

Cottage

Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(119)

$2117.3

/ Nightly

Private Vacation Home

Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(62)

$898.73

/ Nightly

Private Vacation Home

Casa Chiquita-The Coziest in Town, 3 Bed, 3 full Bath, Spa & Pool

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(38)

$656.98

/ Nightly

Cottage

Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(21)

$160.26

/ Nightly

Private Vacation Home

Private Healdsburg Retreat, 1.5 walk to town Plaza, nearby bus shuttle

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(61)

$578.4

/ Nightly

Guest House

Luxe Guest Suite in Dry Creek 5 Mins From Town!

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(193)

$773.1

/ Nightly

Private Vacation Home

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(46)

$1595.67

/ Nightly

Private Vacation Home

Private 3 Bed + Cottage Wine Country Estate With Pool And More

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(342)

$444.48

/ Nightly

Private Vacation Home

Wooded Restful Retreat, with broad scenic views, outdoor dining

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(30)

$978.6

/ Nightly

Private Vacation Home

Beautiful ArtHaus with Pool, Hot Tub, and Sauna!

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(3)

$1815.1

/ Nightly

Villa

Exceptional Estate Vineyards in Healdsburg Sonoma County

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(6)

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Private Vacation Home

Escape to Dry Creek Valley in Healdsburg in a Beautifully Renovated Farm House

Healdsburg, California, United States

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Bath

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Rent a place that suits your needs

Private vacation home

View 132 Private vacation home

Most popular vacation rentals in Healdsburg

Exceptional(6)

$633.61

/ Nightly

Private vacation home

Sonoma Wine Country Retreat: Private Pool

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(6)

$725.89

/ Nightly

Private vacation home

Healdsburg 2BR Victorian vineyard cottage with mountain views

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(6)

$710.00

/ Nightly

Private vacation home

Beautiful ArtHaus with Pool, Hot Tub, and Sauna!

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$692.13

/ Nightly

Private vacation home

Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg

Healdsburg, California, United States

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Bath

Sleeps

Exceptional(6)

$690.74

/ Nightly

Private vacation home

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$690.11

/ Nightly

Private vacation home

Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$623.98

/ Nightly

Cottage

Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$617.64

/ Nightly

Private vacation home

Wine country retreat

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$620.69

/ Nightly

Private vacation home

Healdsburg Plaza Charmer + Hot Tub

Healdsburg, California, United States

Bed

Bath

Sleeps

Exceptional(6)

$732.13

/ Nightly

Apartment

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, California, United States

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Bath

Sleeps

Vacation Rentals By Owner In Healdsburg, CA

$1508.4

$645.11

$467.7

$555.83

$827.73

$973.8

$239.21

$283.5

$128.18

$2117.3

$898.73

$656.98

$160.26

$578.4

$773.1

$1595.67

$444.48

$978.6

$1815.1

Rent a place that suits your needs

Most popular vacation rentals in Healdsburg

$633.61

$725.89

$710.00

$692.13

$690.74

$690.11

$623.98

$617.64

$620.69

$732.13

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