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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 private bathroom
12–17 Sept
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4.96 out of 5 average rating, 85 reviews
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.98 out of 5 average rating, 183 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Sept
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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
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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, 272 reviews
Place to stay in Healdsburg
three blocks to downtown plaza
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
New place to stay
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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
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
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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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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 321 reviews
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Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Oct
4.99 out of 5 average rating, 72 reviews
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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
12–17 Sept
4.99 out of 5 average rating, 89 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
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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, 140 reviews
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 227 reviews
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Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.93 out of 5 average rating, 482 reviews
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 176 reviews
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Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
3–8 Oct
4.92 out of 5 average rating, 52 reviews
Top guest favourite
Home in Geyserville
Healdsburg Wine Country Oasis, Hot Tub & Bocce
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 86 reviews