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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.97 out of 5 average rating, 690 reviews
Top guest favourite
Home in Healdsburg
10-acre vineyard with a hot tub
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 254 reviews
Top guest favourite
Home in Healdsburg
Architect-designed home on a private vineyard
3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.98 out of 5 average rating, 180 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
New place to stay
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 251 reviews
Top guest favourite
Guest house in Healdsburg
Gourmet breakfast on a private patio
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.95 out of 5 average rating, 205 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Guest house in Healdsburg
Wine country farmette with mountain views
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.98 out of 5 average rating, 323 reviews
Top guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 475 reviews
Top guest favourite
Home in Healdsburg
Vineyard-surrounded cottage with high ceilings
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 489 reviews
Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 314 reviews
Guest favourite
Room in Healdsburg
Tuscan-inspired suite with sweeping hill views
1 bed, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Farm stay in Healdsburg
Eco Modern Casita in the Vineyards
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.92 out of 5 average rating, 100 reviews
Guest favourite
Home in Healdsburg
Vintage 3BR Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
4.88 out of 5 average rating, 57 reviews
Top guest favourite
Home in Healdsburg
Hot tub on 1.5 acres amid vineyards
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Vineyard views from a 2-acre farmhouse
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.92 out of 5 average rating, 131 reviews
Guest favourite
Home in Healdsburg
1880s cottage with hot tub and tastings
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Jul
4.9 out of 5 average rating, 91 reviews
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 210 reviews
Guest favourite
Home in Healdsburg
Vineyard views and a pool in wine country
3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 reviews