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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.96 out of 5 average rating, 495 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 71 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
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, 272 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
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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
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, 266 reviews
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 167 reviews
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Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.99 out of 5 average rating, 139 reviews
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Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 259 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
Guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 133 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
11–16 Sept
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
14–19 Nov
4.93 out of 5 average rating, 180 reviews
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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, 260 reviews
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Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 107 reviews
Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds, 3 bathrooms
22–27 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.99 out of 5 average rating, 130 reviews