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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool
3 bedrooms, 3 beds, 3 private bathrooms
12–17 Jul
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4.92 out of 5 average rating, 101 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
9–14 Aug
5.0 out of 5 average rating, 246 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
6–11 Jul
4.97 out of 5 average rating, 38 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
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
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 115 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
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
11–16 Jul
4.99 out of 5 average rating, 122 reviews
Luxe
Home in Healdsburg
Chalk Hill 360°
4 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 14 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, 179 reviews
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
Superhost
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
5–10 Jul
5.0 out of 5 average rating, 48 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
5–10 Jul
4.97 out of 5 average rating, 116 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, 73 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
11–16 Jul
5.0 out of 5 average rating, 201 reviews
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed
15–20 Jul
5.0 out of 5 average rating, 161 reviews
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
2 bedrooms, 2 queen beds
11–16 Aug
5.0 out of 5 average rating, 28 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds
16–21 Jul
5.0 out of 5 average rating, 36 reviews