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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
16–21 Nov
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4.97 out of 5 average rating, 697 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
5–10 Aug
4.98 out of 5 average rating, 56 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, 261 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 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, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 87 reviews
Guest favourite
Room in Santa Rosa
Lovely older home w/ private rm and bath/tub.
1 single bed, 1 bathroom
30 Aug – 4 Sept
4.86 out of 5 average rating, 897 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.95 out of 5 average rating, 101 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 133 reviews
Guest favourite
Cabin in Occidental
Rustic Yet Luxurious Cabin in the Redwoods
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 627 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 49 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 653 reviews
Luxe
Home in Healdsburg
3 BR with Saltwater Pool | Pool House | Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Glen Ellen
Napa Sonoma Airstream with Pool (New)
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 361 reviews