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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 beds, 2 private bathrooms
13–18 Sept
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4.93 out of 5 average rating, 178 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, 263 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, 898 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 52 reviews
Superhost
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.94 out of 5 average rating, 234 reviews
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed, 1 bathroom
16–21 Nov
4.97 out of 5 average rating, 705 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, 56 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 655 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
4.96 out of 5 average rating, 83 reviews
Top guest favourite
Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 218 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
4.99 out of 5 average rating, 88 reviews
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, 367 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
15–20 Aug
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 131 reviews
Top guest favourite
Cottage in Occidental
The Perch - Outdoor Clawfoot Tub
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 843 reviews
Top guest favourite
Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 371 reviews
Top guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 178 reviews