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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, 254 reviews
Top guest favourite
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
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
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Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
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
12–17 Jul
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 126 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
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
Top guest favourite
Home in Geyserville
Updated 5 BR house w/ hot tub - walk to downtown!
4.99 out of 5 average rating, 139 reviews, 5 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
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Home in Geyserville
Sanctuary Estate - Wine Tastings Included
4.95 out of 5 average rating, 73 reviews, 6 bedrooms, 10 beds, 5.5 bathrooms
26–31 Jul
Top guest favourite
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
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
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 28 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
10–15 Aug
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Guest favourite
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
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
5.0 out of 5 average rating, 37 reviews, 3 bedrooms, 6 beds, 4 bathrooms
16–21 Jul
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
4.93 out of 5 average rating, 174 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Aug
Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4.86 out of 5 average rating, 156 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4.97 out of 5 average rating, 231 reviews, 4 bedrooms, 4 beds, 3 bathrooms
17–22 Aug