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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 325 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 257 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 119 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 86 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
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Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
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Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
1–6 Aug
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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 209 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
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Treehouse in Occidental
The Spectacular Spyglass Treehouse
4.98 out of 5 average rating, 360 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 68 reviews, 2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 257 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
4.84 out of 5 average rating, 90 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4.95 out of 5 average rating, 63 reviews, 4 bedrooms, 7 beds, 3 bathrooms
9–14 Aug
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
4.97 out of 5 average rating, 254 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
4.92 out of 5 average rating, 49 reviews, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug