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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 bed, 1 private bathroom
18–23 Aug
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4.99 out of 5 average rating, 318 reviews
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
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, 261 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
10–15 Aug
5.0 out of 5 average rating, 51 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
10–15 Aug
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
10–15 Aug
4.96 out of 5 average rating, 83 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed
10–15 Aug
4.92 out of 5 average rating, 101 reviews
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.96 out of 5 average rating, 492 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 215 reviews
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Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds
16–21 Aug
4.92 out of 5 average rating, 152 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed
15–20 Sept
4.99 out of 5 average rating, 88 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, 479 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 363 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 71 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds
7–12 Sept
4.9 out of 5 average rating, 93 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 63 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, 627 reviews