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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 480 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
Top guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 152 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, 7 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
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
13–18 Aug
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
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
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.93 out of 5 average rating, 655 reviews
Guest favourite
Home in Healdsburg
Haven at Healdsburg, by Vinifera Homes
3 bedrooms, 4 beds, 4.5 bathrooms
25–30 Oct
4.81 out of 5 average rating, 26 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 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
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, 217 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
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
2 bedrooms, 3 king beds, 3 bathrooms
16–23 Oct
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Place to stay in Sebastopol
"The Hollies" Wine Country Victorian Farmhouse
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 283 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
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 64 reviews