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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 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 272 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.98 out of 5 average rating, 183 reviews
Home in Healdsburg
Wine Country Oasis with Pool, Bocce, Pickleball
4 bedrooms, 8 beds, 3.5 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 106 reviews
Superhost
Home in Healdsburg
Tranquil Retreat with Pool, Hot Tub, & Game Room
3 bedrooms, 3 beds, 3 bathrooms
9–14 Sept
New place to stay
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
10–15 Sept
4.91 out of 5 average rating, 176 reviews
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 167 reviews
Top guest favourite
Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 260 reviews
Superhost
Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 68 reviews
Guest favourite
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 133 reviews
Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 bathrooms
9–14 Sept
4.98 out of 5 average rating, 124 reviews