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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
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
14–19 Jul
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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
14–19 Jul
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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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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
4.95 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
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Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Superhost
Room in Healdsburg
Healdsburg Room at the Best Villa + Views
1 bed, 2 bathrooms
2–7 Aug
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
4.93 out of 5 average rating, 474 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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Home in Healdsburg
The Healdsburg Haven
5.0 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Jul – 1 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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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
Vintage 3BR Home in Healdsburg Wine Country
4.88 out of 5 average rating, 56 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
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Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
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Guest house in Healdsburg
Walk to Wine Country | Parking | Pilates
4.97 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 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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Home in Healdsburg
Vineyard Vue - Wine Tastings Included
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
16–21 Jul
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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