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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.95 out of 5 average rating, 221 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Garden House
4 beds
23–28 Oct
4.93 out of 5 average rating, 655 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 53 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 beds
6–11 Sept
4.96 out of 5 average rating, 84 reviews
Guest favourite
Home in Healdsburg
Healdsburg 2br Cottage with Private Yard!
2 beds
4–9 Oct
4.92 out of 5 average rating, 155 reviews
Home in Healdsburg
Great outdoor space, fire pit & gourmet kitchen
1 queen bed
21–28 Nov
Guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 queen bed
20–25 Sept
4.97 out of 5 average rating, 256 reviews
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
10 beds
1–6 Sept
4.95 out of 5 average rating, 77 reviews
Guest favourite
Villa in Healdsburg
Private Hilltop Estate · Pool · Valley Views
5 beds
10–15 Nov
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
4 beds
20–25 Sept
5.0 out of 5 average rating, 123 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 queen beds
25–30 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Healdsburg
2 Bedroom Flat In Downtown Healdsburg
2 beds
27 Oct – 1 Nov
4.97 out of 5 average rating, 137 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
7 beds
21–26 Sept
4.95 out of 5 average rating, 66 reviews
Top guest favourite
Home in Healdsburg
Wine Country Resort Home | Pool & Spa | Sleeps 12
6 beds
6–11 Sept
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
3 beds
29 Sept – 4 Oct
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 beds
1–6 Sept
4.99 out of 5 average rating, 72 reviews
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
3 beds
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 beds
6–11 Sept
Top guest favourite
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
3 king beds
16–23 Oct
5.0 out of 5 average rating, 117 reviews