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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 private bathrooms
12–17 Jul
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4.98 out of 5 average rating, 180 reviews
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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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
Cuvée House
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 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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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
Superhost
Room in Healdsburg
Healdsburg Room at the Best Villa + Views
1 bed, 2 bathrooms
2–7 Aug
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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
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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
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
4.92 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
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Guest suite in Healdsburg
Jimtown Luxury Suite
5.0 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
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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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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
4.99 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
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Guest house in Healdsburg
Bunkhouse at Side Road Farm
4.99 out of 5 average rating, 254 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 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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Home in Healdsburg
Vintage 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
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug