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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.93 out of 5 average rating, 478 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, 261 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
4–9 Aug
4.98 out of 5 average rating, 56 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds
20–25 Sept
4.88 out of 5 average rating, 68 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, 214 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
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 361 reviews
Top guest favourite
Guest house in Healdsburg
Bucher Vineyard Cottage
1 bedroom, 1 queen bed
25–30 Aug
4.99 out of 5 average rating, 133 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
9–14 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 4 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, 43 reviews
Top guest favourite
Home in Sebastopol
Refined Luxury, Vineyard Views close to Healdsburg
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
3 bedrooms, 4 beds
13–18 Aug
4.98 out of 5 average rating, 127 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
4–9 Aug
New place to stay
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds
23–28 Aug
4.97 out of 5 average rating, 117 reviews
Luxe
Home in Healdsburg
3 BR with Saltwater Pool | Pool House | Healdsburg
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 38 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 94 reviews