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Search results; Over 1,000 homes in Healdsburg
Over 1,000 homes in Healdsburg
Photo 1 of 29
Guest favourite
Guest favourite
Cabin in Healdsburg
Updated Russian River Cabin (beach/river access!)
2 bedrooms
,
·
4 beds
,
·
1.5 private bathrooms
1–6 Oct
1–6 Oct
$3,112 SGD
$2,830 SGD
Show price breakdown
for 5 nights
,
·
4.96 out of 5 average rating, 190 reviews
4.96 (190)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
4–9 Oct
4–9 Oct
$5,516 SGD
Show price breakdown
for 5 nights
$5,516 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 125 reviews
5.0 (125)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
8–13 Nov
8–13 Nov
$4,350 SGD
Show price breakdown
for 5 nights
$4,350 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 29
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
4–9 Oct
4–9 Oct
$5,999 SGD
$5,195 SGD
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for 5 nights
4.98 out of 5 average rating, 184 reviews
4.98 (184)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
10–15 Oct
10–15 Oct
$7,179 SGD
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for 5 nights
$7,179 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 102 reviews
4.94 (102)
Photo 1 of 29
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
3–8 Oct
3–8 Oct
$11,057 SGD
$8,370 SGD
Show price breakdown
for 5 nights
4.92 out of 5 average rating, 53 reviews
4.92 (53)
Photo 1 of 29
Luxe
Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms
7 bedrooms
,
·
9 beds
9 beds
,
·
7 bathrooms
7 bathrooms
19–24 Oct
19–24 Oct
$24,303 SGD
$20,209 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Photo 1 of 29
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
$2,967 SGD
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for 5 nights
$2,967 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 275 reviews
5.0 (275)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$2,577 SGD
$2,257 SGD
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for 5 nights
Free cancellation
4.92 out of 5 average rating, 134 reviews
4.92 (134)
Photo 1 of 29
Luxe
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
25–30 Oct
25–30 Oct
$8,211 SGD
$7,477 SGD
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for 5 nights
Book early to save
Free cancellation
5.0 out of 5 average rating, 43 reviews
5.0 (43)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
22–27 Oct
22–27 Oct
$4,424 SGD
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for 5 nights
$4,424 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 27
Top guest favourite
Guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$6,109 SGD
$5,350 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Photo 1 of 29
Top guest favourite
Guest favourite
Guest suite in Healdsburg
Jimtown Luxury Suite
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
11–16 Nov
11–16 Nov
$2,502 SGD
$2,195 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 99 reviews
5.0 (99)
Photo 1 of 29
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
14–19 Nov
14–19 Nov
$11,866 SGD
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for 5 nights
$11,866 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 19 reviews
4.95 (19)
Photo 1 of 7
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
1–6 Oct
1–6 Oct
$27,103 SGD
$23,037 SGD
Show price breakdown
for 5 nights
Free cancellation
Photo 1 of 29
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
$4,755 SGD
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for 5 nights
$4,755 SGD for 5 nights
4.93 out of 5 average rating, 181 reviews
4.93 (181)
Photo 1 of 29
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3.5 bathrooms
3.5 bathrooms
5–10 Oct
5–10 Oct
$10,676 SGD
$8,618 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
28 Oct – 2 Nov
28 Oct – 2 Nov
$5,372 SGD
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for 5 nights
$5,372 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 76 reviews
4.99 (76)
Photo 1 of 22
Top guest favourite
Guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$1,421 SGD
$1,197 SGD
Show price breakdown
for 5 nights
4.99 out of 5 average rating, 135 reviews
4.99 (135)
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