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Search results; Over 1,000 homes in Healdsburg

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
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
8–13 Aug
4.98 out of 5 average rating, 56 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
9–14 Aug
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
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
23–28 Aug
5.0 out of 5 average rating, 215 reviews
Top guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds
20–25 Aug
4.99 out of 5 average rating, 72 reviews
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, 6 reviews
Guest favourite
Room in Santa Rosa
Lovely older home w/ private rm and bath/tub.
1 single bed
30 Aug – 4 Sept
4.86 out of 5 average rating, 898 reviews
Top guest favourite
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
Cabin in Cazadero
Architect cabin in the Redwoods
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 974 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
Top guest favourite
Home in Glen Ellen
Napa Sonoma Airstream with Pool (New)
1 bedroom, 1 bed
14–19 Sept
4.96 out of 5 average rating, 53 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, 841 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
Top guest favourite
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
2 bedrooms, 3 king beds
16–23 Oct
5.0 out of 5 average rating, 117 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, 362 reviews