Home Vacation Rentals By Owner In Healdsburg, CA

Showing 40 Of 170 Vacation Rentals
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Exceptional(2)

$324.59

/ Nightly
Cottage

Chic wine country cottage and garden

Healdsburg, California, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(52)

$260.04

/ Nightly
Cottage

Vineyard Cottage w/ Fire Pit | Chalk Hill Wine Country

Healdsburg, California, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$899.37

/ Nightly
Private Vacation Home

WINE COUNTRY CHIC AND ELEGANCE! BEST LOCATION! TURN KEY!

Healdsburg, California, United States

Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(20)

$869.06

/ Nightly
Private Vacation Home

6Beds 3Bath - Pool, Hot Tub, Pets Welcome, Fire Pit- 1mi to Downtown

Healdsburg, California, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Exceptional(2)

$272.17

/ Nightly
Private Vacation Home

Modern Townhome - Walking Distance to Healdsburg Plaza

Healdsburg, California, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(46)

$959.78

/ Nightly
Private Vacation Home

Rendezvous Under the Oaks-Pool & hot Spa

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(51)

$1063.88

/ Nightly
Private Vacation Home

Wake Up in Your Own Private Vineyard - Healdsburg

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$499.45

/ Nightly
Private Vacation Home

Private Acre+BBQ Patio | 5min to Healdsburg Plaza

Healdsburg, California, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(20)

$862.29

/ Nightly
Private Vacation Home

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(25)

$483.84

/ Nightly
Cottage

Creekside Cottage and Bungalow. Cozy, pet friendly, close to town. Sleeps 6

Healdsburg, California, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$923.45

/ Nightly
Private Vacation Home

Healdsburg Gorgeous Farmhouse for 10, Pool,Spa,BBQ

Healdsburg, California, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(58)

$1035.69

/ Nightly
Private Vacation Home

Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$3156.13

/ Nightly
Private Vacation Home

The Barn Villa

Healdsburg, California, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(43)

$1333.5

/ Nightly
Private Vacation Home

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$821.72

/ Nightly
Private Vacation Home

The Grove on Alexander Valley

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$361

/ Nightly
Cottage

Premier Wine Country Getaway. Exclusive Bucher Vineyard Cottage on Westside Road

Healdsburg, California, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(27)

$941

/ Nightly
Private Vacation Home

Healdsburg House - Chiquita Road - Hot Tub - Private

Healdsburg, California, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(46)

$1235.7

/ Nightly
Private Vacation Home

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$4568.73

/ Nightly
Private Vacation Home

Luxury Healdsburg Estate & Vines

Healdsburg, California, United States

Bed 5

Bed

Bath 5

Bath

Sleep 12

Sleeps
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Exceptional(3)

$2135.65

/ Nightly
Private Vacation Home

Private Oasis in Healdsburg: Pool, Spa & Views

Healdsburg, California, United States

Bed 3

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Home Most popular vacation rentals in Healdsburg

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Exceptional(3)

$633.61

/ Nightly
Private vacation home

Sonoma Wine Country Retreat: Private Pool

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$725.89

/ Nightly
Private vacation home

Healdsburg 2BR Victorian vineyard cottage with mountain views

Healdsburg, California, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(3)

$710.00

/ Nightly
Private vacation home

Beautiful ArtHaus with Pool, Hot Tub, and Sauna!

Healdsburg, California, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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Exceptional(3)

$692.13

/ Nightly
Private vacation home

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

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(3)

$690.74

/ Nightly
Private vacation home

Heron House - Hot Tub and Wine Tastings Included

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(3)

$690.11

/ Nightly
Private vacation home

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

Healdsburg, California, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(3)

$623.98

/ Nightly
Cottage

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

Healdsburg, California, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(3)

$617.64

/ Nightly
Private vacation home

Wine country retreat

Healdsburg, California, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(3)

$620.69

/ Nightly
Private vacation home

Healdsburg Plaza Charmer + Hot Tub

Healdsburg, California, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(3)

$732.13

/ Nightly
Apartment

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, California, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

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