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Search results; Over 1,000 homes in Healdsburg
Over 1,000 homes in Healdsburg
Photo 1 of 6
Top guest favourite
Guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom
,
·
1 bed
,
·
1 private bathroom
11–16 Oct
11–16 Oct
$1,375 SGD
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for 5 nights
$1,375 SGD for 5 nights
,
·
4.95 out of 5 average rating, 221 reviews
4.95 (221)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$6,117 SGD
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for 5 nights
$6,117 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms
6 bedrooms
,
·
10 beds
10 beds
,
·
5.5 bathrooms
5.5 bathrooms
1–6 Sept
1–6 Sept
$13,006 SGD
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for 5 nights
$13,006 SGD for 5 nights
4.95 out of 5 average rating, 77 reviews
4.95 (77)
Photo 1 of 6
Guest favourite
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$9,241 SGD
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for 5 nights
$9,241 SGD for 5 nights
5.0 out of 5 average rating, 73 reviews
5.0 (73)
Photo 1 of 6
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
6–11 Sept
6–11 Sept
$25,609 SGD
$21,767 SGD
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for 5 nights
Free cancellation
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
20–25 Sept
20–25 Sept
$10,586 SGD
$8,262 SGD
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for 5 nights
4.92 out of 5 average rating, 51 reviews
4.92 (51)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$5,048 SGD
$4,601 SGD
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for 5 nights
Book early to save
5.0 out of 5 average rating, 75 reviews
5.0 (75)
Photo 1 of 6
Top guest favourite
Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
,
·
3.5 bathrooms
3.5 bathrooms
11–16 Sept
11–16 Sept
$7,535 SGD
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for 5 nights
$7,535 SGD for 5 nights
4.99 out of 5 average rating, 89 reviews
4.99 (89)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
16–21 Nov
16–21 Nov
$1,774 SGD
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for 5 nights
$1,774 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 98 reviews
4.96 (98)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
$3,046 SGD
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for 5 nights
$3,046 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 268 reviews
5.0 (268)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
$5,635 SGD
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for 5 nights
$5,635 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 123 reviews
5.0 (123)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Nov
1–6 Nov
$3,927 SGD
Show price breakdown
for 5 nights
$3,927 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
7–12 Sept
7–12 Sept
$12,209 SGD
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for 5 nights
$12,209 SGD for 5 nights
5.0 out of 5 average rating, 106 reviews
5.0 (106)
Photo 1 of 6
Top guest favourite
Guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
20–25 Oct
20–25 Oct
$2,475 SGD
$1,562 SGD
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for 5 nights
Free cancellation
4.99 out of 5 average rating, 181 reviews
4.99 (181)
Photo 1 of 6
Luxe
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4.5 bathrooms
4.5 bathrooms
7–12 Sept
7–12 Sept
$12,499 SGD
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for 5 nights
$12,499 SGD for 5 nights
5.0 out of 5 average rating, 95 reviews
5.0 (95)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
21–26 Sept
21–26 Sept
$3,942 SGD
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for 5 nights
$3,942 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
,
·
2 bathrooms
2 bathrooms
14–19 Nov
14–19 Nov
$4,571 SGD
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for 5 nights
$4,571 SGD for 5 nights
4.93 out of 5 average rating, 179 reviews
4.93 (179)
Photo 1 of 6
Guest favourite
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$3,599 SGD
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for 5 nights
$3,599 SGD for 5 nights
4.96 out of 5 average rating, 84 reviews
4.96 (84)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Sept
7–12 Sept
$4,749 SGD
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for 5 nights
$4,749 SGD for 5 nights
4.85 out of 5 average rating, 157 reviews
4.85 (157)
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