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Search results; Over 1,000 homes in Healdsburg
Over 1,000 homes in Healdsburg
Top guest favourite
Guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed
,
·
1 private bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$1,913 SGD
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for 5 nights
$1,913 SGD for 5 nights
,
·
4.97 out of 5 average rating, 690 reviews
4.97 (690)
Top guest favourite
Guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews
5.0 (254)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
$3,077 SGD
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for 5 nights
$3,077 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews
4.98 (85)
,
·
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
21–26 Oct
21–26 Oct
$7,707 SGD
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for 5 nights
$7,707 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 205 reviews
5.0 (205)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$3,352 SGD
$3,037 SGD
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for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 117 reviews
5.0 (117)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
24–29 Aug
24–29 Aug
$5,994 SGD
Show price breakdown
for 5 nights
$5,994 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews
4.98 (61)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
25–30 Aug
25–30 Aug
$5,888 SGD
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for 5 nights
$5,888 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews
4.98 (55)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
21–26 Jul
21–26 Jul
$4,417 SGD
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for 5 nights
$4,417 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 100 reviews
4.95 (100)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$6,683 SGD
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for 5 nights
$6,683 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews
4.98 (180)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$6,846 SGD
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for 5 nights
$6,846 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 129 reviews
4.99 (129)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,180 SGD
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for 5 nights
$2,180 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 48 reviews
5.0 (48)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$5,559 SGD
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for 5 nights
$5,559 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.98 out of 5 average rating, 40 reviews
4.98 (40)
,
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3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$2,952 SGD
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for 5 nights
$2,952 SGD for 5 nights
Pay $0 today
Free cancellation
Luxe
Luxe
Home in Healdsburg
Chalk Hill 360°
5.0 out of 5 average rating, 16 reviews
5.0 (16)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Jul
13–18 Jul
$18,579 SGD
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for 5 nights
$18,579 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 255 reviews
4.92 (255)
,
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2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$4,009 SGD
$2,501 SGD
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for 5 nights
Superhost
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4.95 out of 5 average rating, 61 reviews
4.95 (61)
,
·
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$9,589 SGD
$6,062 SGD
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for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews
4.94 (195)
,
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$3,039 SGD
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for 5 nights
$3,039 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4.97 out of 5 average rating, 231 reviews
4.97 (231)
,
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4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
17–22 Aug
17–22 Aug
$3,389 SGD
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for 5 nights
$3,389 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
5.0 out of 5 average rating, 65 reviews
5.0 (65)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
$4,458 SGD
Show price breakdown
for 5 nights
$4,458 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 31 reviews
5.0 (31)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
3 bathrooms
3 bathrooms
25–30 Aug
25–30 Aug
$5,258 SGD
Show price breakdown
for 5 nights
$5,258 SGD for 5 nights
Free cancellation
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