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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 beds, 2 private bathrooms
13–18 Sept
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4.93 out of 5 average rating, 178 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, 263 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, 119 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
22–27 Aug
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 218 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds
13–18 Aug
4.97 out of 5 average rating, 110 reviews
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 254 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, 7 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
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
13–18 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 365 reviews
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 102 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds
31 Aug – 5 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds
7–12 Sept
4.97 out of 5 average rating, 237 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds
14–19 Nov
4.98 out of 5 average rating, 86 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds
13–18 Aug
Top guest favourite
Home in Sebastopol
Refined Luxury, Vineyard Views close to Healdsburg
4 bedrooms, 5 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 17 reviews