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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, 251 reviews
Top guest favourite
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
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
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 84 reviews, 4 bedrooms, 6 beds, 4 bathrooms
31 Jul – 5 Aug
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Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
24–29 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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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
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
4.94 out of 5 average rating, 195 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Jul
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
Healdsburg Garden House
4.93 out of 5 average rating, 650 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
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Home in Geyserville
Updated 5 BR house w/ hot tub - walk to downtown!
4.99 out of 5 average rating, 138 reviews, 5 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
4.97 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
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Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
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Holiday home in Healdsburg
Downtown Healdsburg Hideaway
4.98 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
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Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
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Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
5.0 out of 5 average rating, 46 reviews, 8 bedrooms, 8 beds, 9 bathrooms
19–24 Jul