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Search results; Over 1,000 homes in Healdsburg

Flat in Healdsburg
Luxurious Cloud Suite in downtown Healdsburg
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.86 out of 5 average rating, 43 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 6 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
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
25–30 Oct
5.0 out of 5 average rating, 272 reviews
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Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
22–27 Oct
4.99 out of 5 average rating, 76 reviews
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 49 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
12–17 Sept
4.96 out of 5 average rating, 85 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 102 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed
2–7 Nov
4.99 out of 5 average rating, 321 reviews
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Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 157 reviews
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Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
4–9 Oct
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
3 bedrooms, 4 beds
29 Oct – 3 Nov
4.9 out of 5 average rating, 40 reviews
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Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
4–9 Oct
5.0 out of 5 average rating, 33 reviews
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Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds
14–19 Sept
4.95 out of 5 average rating, 77 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed
25–30 Oct
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds
12–17 Sept
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds
27 Oct – 1 Nov
4.97 out of 5 average rating, 140 reviews