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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool
3 bedrooms, 3 beds, 3 private bathrooms
30 Aug – 4 Sept
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4.9 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
6–11 Aug
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, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 261 reviews
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Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 87 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, 897 reviews
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 214 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 101 reviews
Luxe
Home in Healdsburg
3 BR with Saltwater Pool | Pool House | Healdsburg
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 130 reviews
Guest favourite
Cabin in Occidental
Rustic Yet Luxurious Cabin in the Redwoods
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 627 reviews
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.85 out of 5 average rating, 91 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 49 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 653 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 70 reviews