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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 255 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 254 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds
20–25 Jul
New place to stay
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
16–21 Jul
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
21–26 Jul
4.98 out of 5 average rating, 55 reviews
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms, 8 beds
19–24 Jul
New place to stay
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 bedroom, 1 king bed
25–30 Aug
5.0 out of 5 average rating, 164 reviews
Superhost
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 205 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds
25–30 Oct
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds
19–24 Aug
4.88 out of 5 average rating, 66 reviews
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
3 bedrooms, 3 beds
3–8 Oct
4.99 out of 5 average rating, 367 reviews
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds
19–24 Jul
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
27 Oct – 1 Nov
4.97 out of 5 average rating, 690 reviews
Guest favourite
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
1 bedroom, 1 queen bed
10–15 Oct
4.95 out of 5 average rating, 226 reviews