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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 261 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 119 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 215 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
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, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 182 reviews
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 128 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
11–16 Aug
4.97 out of 5 average rating, 110 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 25 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
4.95 out of 5 average rating, 65 reviews
Guest favourite
Home in Santa Rosa
Sky View: Heated Pool & Hot Tub, 5 Acres
4 bedrooms, 5 beds, 4 bathrooms
9–14 Sept
4.99 out of 5 average rating, 70 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Guest favourite
Home in Santa Rosa
Titan: Theater, Heated Pool, Gym, Billiards
5 bedrooms, 8 beds, 4 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews