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Search results; Over 1,000 homes in Healdsburg

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Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.95 out of 5 average rating, 221 reviews
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Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
13–18 Oct
4.98 out of 5 average rating, 327 reviews
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Top guest favourite
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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Top guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 180 reviews
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Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 77 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, 268 reviews
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Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.92 out of 5 average rating, 480 reviews
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Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
6–11 Sept
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Guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 213 reviews
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Top guest favourite
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, 258 reviews
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Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
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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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Superhost
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 74 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 bathroom
20–25 Sept
5.0 out of 5 average rating, 167 reviews
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Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
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Top guest favourite
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, 137 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, 179 reviews