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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 bed, 1 private bathroom
23–28 Oct
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4.97 out of 5 average rating, 256 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
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
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 133 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
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Oct
4.99 out of 5 average rating, 72 reviews
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
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
8–13 Sept
4.91 out of 5 average rating, 176 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 6 reviews
Luxe
Villa in Healdsburg
Luxury Villa, 7 minutes from Healdsburg Plaza.
4 bedrooms, 5 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 38 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
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Sept
4.99 out of 5 average rating, 89 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 95 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, 271 reviews
Home in Healdsburg
Wine Country Oasis with Pool, Bocce, Pickleball
4 bedrooms, 8 beds, 3.5 bathrooms
8–13 Sept
New place to stay
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 40 reviews