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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 private bathroom
12–17 Jul
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4.92 out of 5 average rating, 147 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
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 9 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
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
5–10 Jul
4.89 out of 5 average rating, 209 reviews
Guest favourite
Guest house in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 249 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, 195 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, 123 reviews
Guest favourite
Home in Healdsburg
Vintage Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
4.87 out of 5 average rating, 53 reviews
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.92 out of 5 average rating, 253 reviews
Top guest favourite
Farm stay in Geyserville
Country Barn in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Jul
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jul
4.96 out of 5 average rating, 486 reviews
Top guest favourite
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 179 reviews
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.88 out of 5 average rating, 50 reviews
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 320 reviews