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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, 257 reviews
Guest favourite
Room in Healdsburg
Italian Room · Healdsburg Stay · Breakfast
5.0 out of 5 average rating, 10 reviews, 1 bed, 2 bathrooms
17–22 Aug
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
4.98 out of 5 average rating, 325 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Aug
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Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
4.97 out of 5 average rating, 254 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Place to stay in Healdsburg
Modern Vineyard Farmhouse - Zinfandel Room
4.98 out of 5 average rating, 41 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
4.96 out of 5 average rating, 491 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest house in Healdsburg
The Roost - Garden Studio
5.0 out of 5 average rating, 67 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Home in Healdsburg
Great outdoor space, fire pit & gourmet kitchen
1 bedroom, 1 bed, 1 bathroom
21–28 Nov
Guest favourite
Home in Healdsburg
Spacious Healdsburg Home - Walk to the Square!
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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Home in Healdsburg
Healdsburg Garden House
4.93 out of 5 average rating, 653 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
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Guest suite in Healdsburg
Jimtown Luxury Suite
5.0 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
5.0 out of 5 average rating, 49 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
4.92 out of 5 average rating, 257 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
4.98 out of 5 average rating, 82 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
4.84 out of 5 average rating, 90 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Healdsburg
Bucher Vineyard Studio
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
4.93 out of 5 average rating, 164 reviews, 1 queen bed, 1 bathroom
2–7 Aug