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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
The Wine Ranch
3 bedrooms, 5 beds, 2.5 private bathrooms
7–12 Sept
,
4.93 out of 5 average rating, 297 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 367 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
4.95 out of 5 average rating, 226 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Oct
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
4.96 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
4.99 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Luxe
Home in Sonoma
Luxury Modern Home w/ Infinity Pool - 3400 sq ft
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
27 Sept – 2 Oct
Superhost
Home in Healdsburg
The Grove on Alexander Valley
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
4.95 out of 5 average rating, 101 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
4.99 out of 5 average rating, 126 reviews, 3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
5–10 Oct