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Search results; Over 1,000 homes in Healdsburg
Over 1,000 homes in Healdsburg
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
$1,314 SGD
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for 5 nights
$1,314 SGD for 5 nights
,
·
4.95 out of 5 average rating, 221 reviews
4.95 (221)
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
$5,629 SGD
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for 5 nights
$5,629 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 123 reviews
5.0 (123)
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
$3,979 SGD
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for 5 nights
$3,979 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (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
$3,032 SGD
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for 5 nights
$3,032 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 268 reviews
5.0 (268)
Top guest favourite
Guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$2,827 SGD
$2,590 SGD
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for 5 nights
Book early to save
Free cancellation
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Luxe
Luxe
Villa in Healdsburg
Wine Country Estate
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
5 bathrooms
5 bathrooms
7–12 Sept
7–12 Sept
$16,957 SGD
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for 5 nights
$16,957 SGD for 5 nights
5.0 out of 5 average rating, 16 reviews
5.0 (16)
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
2–7 Sept
2–7 Sept
$15,383 SGD
$13,931 SGD
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for 5 nights
4.95 out of 5 average rating, 77 reviews
4.95 (77)
Guest favourite
Guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$2,517 SGD
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for 5 nights
$2,517 SGD for 5 nights
4.97 out of 5 average rating, 256 reviews
4.97 (256)
Guest favourite
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$2,150 SGD
$1,899 SGD
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for 5 nights
Free cancellation
4.92 out of 5 average rating, 155 reviews
4.92 (155)
Top guest favourite
Guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms
8 bedrooms
,
·
8 beds
8 beds
,
·
9 bathrooms
9 bathrooms
7–12 Sept
7–12 Sept
$15,395 SGD
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for 5 nights
$15,395 SGD for 5 nights
5.0 out of 5 average rating, 49 reviews
5.0 (49)
Guest favourite
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$6,200 SGD
$4,683 SGD
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for 5 nights
4.88 out of 5 average rating, 72 reviews
4.88 (72)
Guest favourite
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$3,820 SGD
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for 5 nights
$3,820 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 112 reviews
4.96 (112)
Guest favourite
Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
6 bedrooms
6 bedrooms
,
·
5 beds
5 beds
,
·
6 bathrooms
6 bathrooms
10–15 Nov
10–15 Nov
$13,127 SGD
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for 5 nights
$13,127 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 19 reviews
4.95 (19)
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
$12,143 SGD
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for 5 nights
$12,143 SGD for 5 nights
5.0 out of 5 average rating, 95 reviews
5.0 (95)
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
$9,231 SGD
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for 5 nights
$9,231 SGD for 5 nights
5.0 out of 5 average rating, 73 reviews
5.0 (73)
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
$6,747 SGD
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for 5 nights
$6,747 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Guest favourite
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
4.5 bathrooms
4.5 bathrooms
5–10 Sept
5–10 Sept
$11,513 SGD
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for 5 nights
$11,513 SGD for 5 nights
4.91 out of 5 average rating, 176 reviews
4.91 (176)
Top guest favourite
Guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$6,096 SGD
$5,338 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 53 reviews
5.0 (53)
Top guest favourite
Guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$2,947 SGD
Show price breakdown
for 5 nights
$2,947 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 137 reviews
4.97 (137)
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