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Search results; Over 1,000 homes in Healdsburg

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Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Fitch Mountain
3 bedrooms, 3 beds, 3 shared bathrooms
17–22 Oct
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5.0 out of 5 average rating, 24 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg Inn on the Plaza, Healdsburg interior .
1 bedroom, 1 king bed
25–30 Oct
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds
8–13 Nov
4.92 out of 5 average rating, 134 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 126 reviews
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Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
10–15 Oct
4.94 out of 5 average rating, 102 reviews
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Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
4–9 Oct
4.99 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 54 reviews
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Top guest favourite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 bedroom, 1 queen bed
4–9 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
3–8 Oct
4.92 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 275 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds
19–24 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
4–9 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Room in Healdsburg
Modern Vineyard Farmhouse - Cabernet Room
1 bed
1–6 Oct
5.0 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed
11–16 Oct
4.96 out of 5 average rating, 496 reviews
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Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 184 reviews
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Luxe
Home in Healdsburg
Farmstay Estate | Pool, Cedar Hot Tub & Honey Farm
4 bedrooms, 4 king beds
6–11 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed
1–6 Nov
5.0 out of 5 average rating, 168 reviews