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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds, 1.5 private bathrooms
11–16 Sept
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4.85 out of 5 average rating, 158 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.98 out of 5 average rating, 183 reviews
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
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, 272 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
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
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.9 out of 5 average rating, 266 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
10–15 Sept
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 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
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 96 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 9 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
Luxe
Villa in Healdsburg
Private Sonoma Estate: Tennis, Pickleball, Pool
7 bedrooms, 9 beds, 7 bathrooms
14–19 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Healdsburg
Creekside Cottage
2 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
4.96 out of 5 average rating, 92 reviews
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 155 reviews
Top guest favourite
Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 106 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
10–15 Sept
4.98 out of 5 average rating, 124 reviews