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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 private bathroom
27 Jul – 1 Aug
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4.97 out of 5 average rating, 251 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 254 reviews
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
15–20 Jul
4.98 out of 5 average rating, 180 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
15–20 Jul
New place to stay
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed
19–24 Jul
4.95 out of 5 average rating, 205 reviews
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds
19–24 Aug
4.98 out of 5 average rating, 323 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
2–7 Aug
5.0 out of 5 average rating, 48 reviews
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed
16–21 Aug
4.93 out of 5 average rating, 475 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed
2–7 Aug
4.96 out of 5 average rating, 489 reviews
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Room in Windsor
Wine Country Stay
1 queen bed
26–31 Jul
4.9 out of 5 average rating, 210 reviews
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Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed
15–20 Jul
4.92 out of 5 average rating, 100 reviews
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Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
3 bedrooms, 5 beds
19–24 Jul
4.88 out of 5 average rating, 57 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 118 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed
4–9 Oct
4.99 out of 5 average rating, 314 reviews
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed
10–15 Aug
5.0 out of 5 average rating, 164 reviews
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Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
3 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
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Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
2 bedrooms, 4 beds
4–9 Aug
4.99 out of 5 average rating, 81 reviews
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Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds
19–24 Jul
4.92 out of 5 average rating, 131 reviews