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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 323 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 117 reviews
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Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 254 reviews
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
4.99 out of 5 average rating, 126 reviews
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
4.98 out of 5 average rating, 180 reviews
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Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds, 2 bathrooms
16–21 Aug
4.88 out of 5 average rating, 66 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
13–18 Jul
New place to stay
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Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
19–24 Jul
5.0 out of 5 average rating, 46 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 66 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.88 out of 5 average rating, 51 reviews
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Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
26–31 Jul
4.95 out of 5 average rating, 73 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 489 reviews
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Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 134 reviews
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
13–18 Aug
4.93 out of 5 average rating, 174 reviews