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Search results; Over 1,000 homes in Healdsburg

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
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
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 5 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
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
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
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
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 57 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
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
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
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
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
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 70 reviews
Top guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
4.99 out of 5 average rating, 178 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 91 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