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Search results; Over 1,000 homes in Healdsburg

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
Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed
22–27 Aug
5.0 out of 5 average rating, 50 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
21–26 Aug
4.96 out of 5 average rating, 83 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
16–21 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
17–22 Oct
4.98 out of 5 average rating, 368 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
22–27 Aug
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed
16–21 Aug
4.99 out of 5 average rating, 178 reviews
Superhost
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
1 bedroom, 1 queen bed
8–13 Nov
4.94 out of 5 average rating, 234 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 263 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds
20–25 Sept
4.93 out of 5 average rating, 655 reviews
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds
10–15 Sept
4.98 out of 5 average rating, 326 reviews
Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed
16–21 Aug
4.92 out of 5 average rating, 480 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 218 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
16–21 Aug
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed
20–25 Sept
4.99 out of 5 average rating, 88 reviews
Top guest favourite
Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed
21–26 Sept
4.94 out of 5 average rating, 371 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds
29 Sept – 4 Oct
4.99 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed
8–13 Sept
4.99 out of 5 average rating, 131 reviews