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Search results; Over 1,000 homes in Healdsburg

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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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5.0 out of 5 average rating, 164 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
4.95 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
4.93 out of 5 average rating, 475 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
4.97 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
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Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
5.0 out of 5 average rating, 9 reviews, 1 bed, 2 bathrooms
2–7 Aug
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
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Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 489 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 323 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Aug
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Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
4.9 out of 5 average rating, 91 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
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Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
4.92 out of 5 average rating, 100 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
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Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
4.88 out of 5 average rating, 57 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
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Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
4.99 out of 5 average rating, 71 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
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Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
4.99 out of 5 average rating, 81 reviews, 2 bedrooms, 4 beds, 2 bathrooms
4–9 Aug