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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 private bathrooms
17–22 Oct
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4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
4–9 Oct
5.0 out of 5 average rating, 248 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
11–16 Jul
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
3 bedrooms, 3 queen beds
24–29 Jul
4.97 out of 5 average rating, 39 reviews
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds
5–10 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
31 Jul – 5 Aug
4.98 out of 5 average rating, 83 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds
5–10 Jul
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
5–10 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
6–11 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds
13–18 Jul
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds
5–10 Jul
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds
3–8 Jul
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds
2–7 Aug
4.93 out of 5 average rating, 650 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
14–19 Sept
4.95 out of 5 average rating, 99 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
23–28 Aug
5.0 out of 5 average rating, 28 reviews
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
5–10 Jul
4.97 out of 5 average rating, 79 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
12–17 Jul
New place to stay