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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
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4.97 out of 5 average rating, 29 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
8–13 Sept
4.98 out of 5 average rating, 183 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
8–13 Sept
Home in Healdsburg
Wine Country Oasis with Pool, Bocce, Pickleball
4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Sept
New place to stay
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 495 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
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 2 beds, 1 bathroom
16–21 Nov
4.98 out of 5 average rating, 328 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 321 reviews
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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
Superhost
Home in Healdsburg
Tranquil Retreat with Pool, Hot Tub, & Game Room
3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept
New place to stay
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
8–13 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
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
9–14 Sept
4.91 out of 5 average rating, 176 reviews
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Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 106 reviews
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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
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
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 95 reviews