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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 private bathrooms
5–10 Jul
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4.98 out of 5 average rating, 179 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 246 reviews
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
4.99 out of 5 average rating, 122 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa near Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
6–11 Jul
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Geyserville
Luxurious Wine Country Estate
8 bedrooms, 8 beds, 9 bathrooms
1–6 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
3–8 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
6–11 Jul
4.95 out of 5 average rating, 60 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 194 reviews
Top guest favourite
Home in Windsor
Casa de la Esperanza: 1890s Gem - Hot Tub - 5BD/3BA
5 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 74 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 99 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Jul
4.9 out of 5 average rating, 91 reviews
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 161 reviews
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
New place to stay
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
20–25 Jul
4.95 out of 5 average rating, 60 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.97 out of 5 average rating, 109 reviews
Guest favourite
Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
4.87 out of 5 average rating, 53 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 28 reviews