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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 254 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
13–18 Jul
New place to stay
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Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
4.98 out of 5 average rating, 180 reviews
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Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 205 reviews
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Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 323 reviews
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Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 37 reviews
Superhost
Room in Healdsburg
Healdsburg Room at the Best Villa + Views
1 bed, 2 bathrooms
2–7 Aug
Guest favourite
Home in Healdsburg
New! Healdsburg Poolside Orchard Getaway
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 reviews
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Guest house in Healdsburg
Walk to Wine Country | Parking | Pilates
1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 251 reviews
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Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 65 reviews
Guest favourite
Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
4.88 out of 5 average rating, 56 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 117 reviews
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Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 314 reviews
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Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Jul
4.99 out of 5 average rating, 89 reviews
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 489 reviews
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Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.92 out of 5 average rating, 131 reviews
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.88 out of 5 average rating, 51 reviews