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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 256 reviews
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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, 256 reviews
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Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 253 reviews
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Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
4.98 out of 5 average rating, 56 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds, 5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 181 reviews
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Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
15–20 Aug
4.95 out of 5 average rating, 62 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 49 reviews
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Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Room in Santa Rosa
Golf Course Sanctuary-Designed for Travel Nurses
1 queen bed, 1 bathroom
1–6 Aug
New place to stay
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
New place to stay
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
4.97 out of 5 average rating, 117 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 368 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 109 reviews
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Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 72 reviews
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Home in Santa Rosa
Donner Dos Wine Country Retreat
2 bedrooms, 2 queen beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Healdsburg
Casa Chiquita - Coziest in town!
3 bedrooms, 3 beds, 3 bathrooms
20–25 Aug
4.97 out of 5 average rating, 104 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 66 reviews
Top guest favourite
Home in Geyserville
Historic Home; Walk to Cyrus, Diavola, Catelli's
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
4.98 out of 5 average rating, 117 reviews