filters

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 beds, 1.5 private bathrooms
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, 1 bathroom
4–9 Aug
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Luxe
Villa in Healdsburg
Wine Country Estate
5 bedrooms, 6 beds, 5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
4.98 out of 5 average rating, 182 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
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.92 out of 5 average rating, 100 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
Top guest favourite
Guest suite in Healdsburg
Jimtown Luxury Suite
1 bedroom, 1 king bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.95 out of 5 average rating, 101 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
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 8 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
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 361 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
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 51 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
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