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Search results; Over 1,000 homes in Healdsburg

Superhost
Cottage in Healdsburg
Riverfront Wine Country Cottage With Views and Spa
2 bedrooms, 3 beds, 1 private bathroom
21–26 Sept
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4.88 out of 5 average rating, 95 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
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds
4–9 Oct
5.0 out of 5 average rating, 8 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, 215 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, 362 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
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
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
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 63 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
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds
17–22 Aug
4.97 out of 5 average rating, 236 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, 44 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds
9–14 Aug
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Cottage in Healdsburg
Bee Haven Cottage
1 bedroom, 1 queen bed
17–22 Aug
5.0 out of 5 average rating, 227 reviews
Top guest favourite
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
22–27 Aug
4.95 out of 5 average rating, 64 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
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds
9–14 Aug
4.97 out of 5 average rating, 110 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, 128 reviews