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Search results; Over 1,000 homes in Healdsburg

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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
9–14 Nov
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4.95 out of 5 average rating, 225 reviews
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Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
29 Oct – 3 Nov
4.9 out of 5 average rating, 10 reviews
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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
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 2 beds, 1 bathroom
16–21 Nov
4.98 out of 5 average rating, 329 reviews
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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
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
11–16 Sept
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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
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
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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
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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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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
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
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Home in Healdsburg
Wine Country Cottage in Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
22–27 Oct
4.89 out of 5 average rating, 426 reviews
Superhost
Home in Healdsburg
Tranquil Retreat with Pool, Hot Tub, & Game Room
3 bedrooms, 3 beds, 3 bathrooms
11–16 Sept
New place to stay
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 9 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
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
Top guest favourite
Home in Healdsburg
Vineyard views, hot tub, sauna, cinema
2 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
4.98 out of 5 average rating, 124 reviews