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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.97 out of 5 average rating, 255 reviews
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 5 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
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, 222 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
21–26 Aug
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 369 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 57 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
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, 89 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
18–23 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
8–13 Nov
4.94 out of 5 average rating, 234 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds
11–16 Oct
4.93 out of 5 average rating, 655 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
18–23 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed
19–24 Aug
4.92 out of 5 average rating, 480 reviews
Top guest favourite
Cottage in Occidental
The Perch - Outdoor Clawfoot Tub
1 bedroom, 1 queen bed
27 Sept – 2 Oct
4.95 out of 5 average rating, 845 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, 70 reviews
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds
6–11 Sept
4.91 out of 5 average rating, 261 reviews
Guest favourite
Cabin in Occidental
Rustic Yet Luxurious Cabin in the Redwoods
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 632 reviews
Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews