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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Mediterranean Getaway with breakfast Healdsburg
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.95 out of 5 average rating, 227 reviews
Room in Healdsburg
three blocks to downtown plaza
1 bed, 1 bathroom
9–14 Jan
New place to stay
Featured hotel
Hotel in Healdsburg
Healdsburg interior king
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
4.9 out of 5 average rating, 10 reviews
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Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 71 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
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 6 reviews
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Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
20–25 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
15–20 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
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Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 85 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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Home in Healdsburg
Dry Creek Valley Cottage
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 495 reviews
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Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.94 out of 5 average rating, 102 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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Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 10 reviews
Home in Healdsburg
Luxe Healdsburg Estate | Pool, Pickleball, Views
4 bedrooms, 8 beds, 3.5 bathrooms
22–27 Sept
New place to stay
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, 74 reviews