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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.98 out of 5 average rating, 57 reviews
Home in Healdsburg
Modern oasis with infinity pool and 2 lush acres
4 bedrooms, 8 beds, 3.5 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 180 reviews
Top guest favourite
Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 258 reviews
Top guest favourite
Home in Geyserville
Sanctuary Estate - Wine Tastings Included
6 bedrooms, 10 beds, 5.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 77 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, 268 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
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
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 72 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
6–11 Sept
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Healdsburg
Wine Country Cottage in Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 425 reviews
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Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 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, 262 reviews
Guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 213 reviews
Top guest favourite
Home in Healdsburg
Spectacular Healdsburg Manor-6beds/4.5B, POOL+SPA!
6 bedrooms, 5 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 44 reviews