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Search results; Over 1,000 homes in Healdsburg

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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
9–14 Nov
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4.95 out of 5 average rating, 222 reviews
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Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 183 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 321 reviews
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Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 133 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 271 reviews
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Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Oct
4.99 out of 5 average rating, 72 reviews
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Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
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Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.99 out of 5 average rating, 138 reviews
Superhost
Home in Healdsburg
Tranquil Retreat with Pool, Hot Tub, & Game Room
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
New place to stay
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Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
20–25 Oct
4.99 out of 5 average rating, 182 reviews
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Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 259 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 102 reviews
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.93 out of 5 average rating, 481 reviews
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Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
8–13 Sept
4.91 out of 5 average rating, 176 reviews
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 167 reviews
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Cottage in Healdsburg
Bee Haven Cottage
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 230 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
7–12 Sept