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Search results; Over 1,000 homes in Healdsburg
Over 1,000 homes in Healdsburg
Top guest favourite
Guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms
,
·
3 beds
,
·
2 private bathrooms
4–9 Oct
4–9 Oct
$5,798 SGD
$4,948 SGD
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for 5 nights
,
·
4.93 out of 5 average rating, 175 reviews
4.93 (175)
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
$3,076 SGD
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for 5 nights
$3,076 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 254 reviews
5.0 (254)
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
5 bathrooms
5 bathrooms
20–25 Jul
20–25 Jul
$5,031 SGD
$4,276 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
24–29 Aug
24–29 Aug
$5,950 SGD
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for 5 nights
$5,950 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 118 reviews
5.0 (118)
Top guest favourite
Guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
21–26 Oct
21–26 Oct
$7,586 SGD
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for 5 nights
$7,586 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 85 reviews
4.98 (85)
Top guest favourite
Guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
21–26 Jul
21–26 Jul
$4,461 SGD
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for 5 nights
$4,461 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 55 reviews
4.98 (55)
Superhost
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
5 bathrooms
5 bathrooms
19–24 Jul
19–24 Jul
$15,023 SGD
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for 5 nights
$15,023 SGD for 5 nights
New place to stay
New
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
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
4.98 out of 5 average rating, 41 reviews
4.98 (41)
Top guest favourite
Guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
18–23 Jul
18–23 Jul
$6,844 SGD
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for 5 nights
$6,844 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 181 reviews
4.98 (181)
Top guest favourite
Guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$4,334 SGD
$3,216 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 206 reviews
5.0 (206)
Top guest favourite
Guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$1,949 SGD
$1,776 SGD
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 98 reviews
4.96 (98)
Top guest favourite
Guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
10–15 Aug
10–15 Aug
$13,554 SGD
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for 5 nights
$13,554 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 126 reviews
4.99 (126)
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
25–30 Aug
25–30 Aug
$14,676 SGD
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for 5 nights
$14,676 SGD for 5 nights
5.0 out of 5 average rating, 94 reviews
5.0 (94)
Guest favourite
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$3,007 SGD
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for 5 nights
$3,007 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 195 reviews
4.94 (195)
Superhost
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$3,975 SGD
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for 5 nights
$3,975 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
26–31 Jul
26–31 Jul
$9,690 SGD
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for 5 nights
$9,690 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 29 reviews
5.0 (29)
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
20–25 Sept
20–25 Sept
$4,456 SGD
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for 5 nights
$4,456 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 66 reviews
5.0 (66)
Guest favourite
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
24–29 Aug
24–29 Aug
$5,523 SGD
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for 5 nights
$5,523 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 24 reviews
4.96 (24)
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
26–31 Jul
26–31 Jul
$3,851 SGD
$3,426 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
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