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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds, 2.5 private bathrooms
2–7 Nov
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4.93 out of 5 average rating, 297 reviews
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, 257 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
1–6 Aug
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
3–8 Aug
4.98 out of 5 average rating, 56 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds
11–16 Aug
5.0 out of 5 average rating, 29 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
23–28 Aug
4.97 out of 5 average rating, 117 reviews
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, 209 reviews
Top guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 359 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
9–14 Aug
4.95 out of 5 average rating, 63 reviews
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
3 bedrooms, 4 beds
16–21 Aug
4.88 out of 5 average rating, 52 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds
2–7 Aug
4.92 out of 5 average rating, 48 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
10–15 Aug
4.99 out of 5 average rating, 127 reviews
Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds
8–13 Aug
4.86 out of 5 average rating, 156 reviews
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds
4–9 Oct
4.93 out of 5 average rating, 176 reviews
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
3 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 reviews