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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 261 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed
9–14 Aug
4.93 out of 5 average rating, 166 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
9–14 Aug
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds
5–10 Sept
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed
9–14 Aug
4.99 out of 5 average rating, 131 reviews
Guest favourite
Place to stay in Healdsburg
Modern Vineyard Farmhouse - Zinfandel Room
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 41 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed
10–15 Aug
4.92 out of 5 average rating, 100 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 362 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 215 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
9–14 Aug
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds
20–25 Sept
4.87 out of 5 average rating, 69 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed
15–20 Sept
4.99 out of 5 average rating, 88 reviews
Guest favourite
Room in Santa Rosa
Lovely older home w/ private rm and bath/tub.
1 single bed
30 Aug – 4 Sept
4.86 out of 5 average rating, 898 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds
1–6 Sept
4.99 out of 5 average rating, 72 reviews
Guest favourite
Guest house in Guerneville
Sweetwater Cottage
1 bedroom, 1 double bed
14–19 Sept
4.95 out of 5 average rating, 271 reviews