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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 bed, 1 private bathroom
25–30 Aug
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5.0 out of 5 average rating, 167 reviews
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Flat in Forestville
Enchanting Russian River Retreat
1 double bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 64 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 492 reviews
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Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 bathrooms
6–11 Aug
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Aug
4.9 out of 5 average rating, 93 reviews
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
4.98 out of 5 average rating, 325 reviews
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Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 653 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 110 reviews
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Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 49 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.92 out of 5 average rating, 100 reviews
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Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed, 1 bathroom
29 Sept – 4 Oct
4.97 out of 5 average rating, 254 reviews
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Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 8 reviews
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Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.94 out of 5 average rating, 370 reviews
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 478 reviews
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Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 164 reviews
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Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
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Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
4–9 Aug
4.98 out of 5 average rating, 56 reviews
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Room in Healdsburg
Modern Vineyard Farmhouse - Cabernet Room
1 bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 44 reviews