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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.97 out of 5 average rating, 689 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, 251 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 313 reviews
Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 204 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
New place to stay
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
1 bed, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.99 out of 5 average rating, 126 reviews
Top guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 473 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 488 reviews
Top guest favourite
Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
2 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
8–13 Jul
4.98 out of 5 average rating, 322 reviews
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Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.84 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Jul
4.99 out of 5 average rating, 75 reviews
Guest favourite
Home in Healdsburg
Wine Country Cottage in Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
5–10 Aug
4.88 out of 5 average rating, 418 reviews
Top guest favourite
Guest house in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.99 out of 5 average rating, 254 reviews
Guest favourite
Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
3 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
5.0 out of 5 average rating, 8 reviews