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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 bed, 1 private bathroom
25–30 Aug
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5.0 out of 5 average rating, 167 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
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 42 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 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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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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Treehouse in Occidental
The Spectacular Spyglass Treehouse
4.98 out of 5 average rating, 359 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
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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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Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Superhost
Home in Healdsburg
The Grove on Alexander Valley
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
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Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 29 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
11–16 Aug
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Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
4.92 out of 5 average rating, 48 reviews, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
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
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Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4.95 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4 bathrooms
15–20 Aug
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Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
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
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4.86 out of 5 average rating, 156 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Aug
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Home in Healdsburg
Rivers Breeze - Wine Tastings Included
4.88 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
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Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 3 bathrooms
20–25 Oct
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Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept