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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
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom
,
·
1 bed
,
·
1 private bathroom
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,826 SGD
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for 5 nights
$2,826 SGD for 5 nights
,
·
4.99 out of 5 average rating, 318 reviews
4.99 (318)
Guest favourite
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$3,793 SGD
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for 5 nights
$3,793 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
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
$3,028 SGD
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for 5 nights
$3,028 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 264 reviews
5.0 (264)
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
$5,784 SGD
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for 5 nights
$5,784 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 122 reviews
5.0 (122)
Top guest favourite
Guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$4,365 SGD
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for 5 nights
$4,365 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 57 reviews
4.98 (57)
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
22–27 Aug
22–27 Aug
$6,737 SGD
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for 5 nights
$6,737 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Top guest favourite
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$7,960 SGD
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for 5 nights
$7,960 SGD for 5 nights
4.98 out of 5 average rating, 371 reviews
4.98 (371)
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
31 Aug – 5 Sept
31 Aug – 5 Sept
$6,341 SGD
$5,646 SGD
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for 5 nights
4.96 out of 5 average rating, 27 reviews
4.96 (27)
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
$12,394 SGD
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for 5 nights
$12,394 SGD for 5 nights
5.0 out of 5 average rating, 94 reviews
5.0 (94)
Top guest favourite
Guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
20–25 Aug
20–25 Aug
$5,330 SGD
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for 5 nights
$5,330 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 52 reviews
5.0 (52)
Top guest favourite
Guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Aug
20–25 Aug
$2,991 SGD
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for 5 nights
$2,991 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
23–28 Aug
23–28 Aug
$2,130 SGD
$1,444 SGD
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for 5 nights
Free cancellation
4.99 out of 5 average rating, 178 reviews
4.99 (178)
Superhost
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$2,533 SGD
$1,752 SGD
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for 5 nights
4.9 out of 5 average rating, 262 reviews
4.9 (262)
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
$2,819 SGD
$2,582 SGD
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for 5 nights
Book early to save
Free cancellation
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Luxe
Luxe
Home in Santa Rosa
Award-Winning Glass House · Pool · Wine Country
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
11–16 Sept
11–16 Sept
$9,527 SGD
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for 5 nights
$9,527 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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
14–19 Nov
14–19 Nov
$5,892 SGD
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for 5 nights
$5,892 SGD for 5 nights
4.98 out of 5 average rating, 89 reviews
4.98 (89)
Guest favourite
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
7–12 Sept
7–12 Sept
$2,913 SGD
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for 5 nights
$2,913 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 238 reviews
4.97 (238)
Guest favourite
Guest favourite
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
28 Aug – 2 Sept
28 Aug – 2 Sept
$6,942 SGD
$4,848 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 65 reviews
4.95 (65)
Top guest favourite
Guest favourite
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,680 SGD
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for 5 nights
$2,680 SGD for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
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