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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 255 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
New place to stay
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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, 253 reviews
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
4.98 out of 5 average rating, 180 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 314 reviews
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 323 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, 474 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 48 reviews
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 205 reviews
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Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 37 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 488 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, 117 reviews
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Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.99 out of 5 average rating, 254 reviews
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Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.99 out of 5 average rating, 126 reviews
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Home in Healdsburg
Wine Country Cottage in Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
5–10 Aug
4.88 out of 5 average rating, 419 reviews
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Home in Healdsburg
Vintage Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
4.88 out of 5 average rating, 56 reviews
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Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
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Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.92 out of 5 average rating, 131 reviews
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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Jul
4.99 out of 5 average rating, 89 reviews