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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 252 reviews
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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
7–12 Jul
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
4.99 out of 5 average rating, 313 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
4.95 out of 5 average rating, 204 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
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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 suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
4.93 out of 5 average rating, 473 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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Flat in Healdsburg
Bucher Vineyard Studio
4.99 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 bed, 1 bathroom
15–20 Nov
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 116 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 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
13–18 Jul
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Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 488 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
4.84 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 4 bathrooms
7–12 Jul
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Home in Healdsburg
Views, hot tub, sauna, cold plunge, cinema!
4.98 out of 5 average rating, 120 reviews, 2 bedrooms, 3 beds, 3 bathrooms
13–18 Jul
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 124 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 322 reviews, 1 bedroom, 3 beds, 1 bathroom
8–13 Jul
Guest favourite
Home in Healdsburg
Wine Country Cottage in Healdsburg
4.88 out of 5 average rating, 418 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 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
11–16 Jul