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Search results; Over 1,000 homes in Healdsburg

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Flat in Healdsburg
Luxurious Garden Suite in downtown Healdsburg
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.83 out of 5 average rating, 141 reviews
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Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 125 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, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 275 reviews
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Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 321 reviews
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Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
28 Oct – 2 Nov
4.99 out of 5 average rating, 76 reviews
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Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 180 reviews
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Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds, 7 bathrooms
18–23 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 157 reviews
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Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 49 reviews
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Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
3–8 Oct
4.92 out of 5 average rating, 53 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 496 reviews
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Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.97 out of 5 average rating, 31 reviews
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 140 reviews
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Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
3 bedrooms, 4 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.9 out of 5 average rating, 41 reviews
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Top guest favourite
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, 483 reviews