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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
Luxury 1-br cottage on 30-acre Healdsburg vineyard
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 133 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 72 reviews
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 52 reviews
Superhost
Home in Healdsburg
Tranquil Retreat with Pool, Hot Tub, & Game Room
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
New place to stay
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Sept
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 74 reviews
Guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 213 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Place to stay in Sebastopol
"The Hollies" Wine Country Victorian Farmhouse
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 284 reviews
Top guest favourite
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, 264 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 371 reviews
Luxe
Villa in Healdsburg
Wine Country Estate
5 bedrooms, 6 beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.85 out of 5 average rating, 157 reviews
Top guest favourite
Cabin in Occidental
Rustic Yet Luxurious Cabin in the Redwoods
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 633 reviews