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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
28 Sept – 3 Oct
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4.97 out of 5 average rating, 688 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 248 reviews
Guest favourite
Guest house in Healdsburg
Walk to Wine Country | Parking | Pilates
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 249 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
Farm stay in Geyserville
Country Barn in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.93 out of 5 average rating, 473 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 180 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, 200 reviews
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 486 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 48 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
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
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
5–10 Jul
4.97 out of 5 average rating, 116 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
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
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
Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 64 reviews