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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
19–24 Aug
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4.98 out of 5 average rating, 323 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
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
9-acre estate with pool and vineyard views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.98 out of 5 average rating, 180 reviews
Superhost
Home in Healdsburg
Vineyard Daydream - Villa with Wine Tastings Inclu
4 bedrooms, 8 beds, 5 bathrooms
19–24 Jul
New place to stay
Luxe
Home in Healdsburg
Honey farm with a hot tub and pool
4 bedrooms, 4 king beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Healdsburg
Vineyard views from a private redwood deck
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Tiny home in Sebastopol
Wine country views with a barrel sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 205 reviews
Top guest favourite
Guest house in Healdsburg
Vineyard views and a private hot tub
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 164 reviews
Top guest favourite
Guest house in Healdsburg
Vineyard cottage with Russian River views
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 129 reviews
Guest favourite
Home in Healdsburg
Private vineyard with complimentary winery tastings
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Aug
4.88 out of 5 average rating, 66 reviews
Top guest favourite
Home in Geyserville
Vineyard home with a spa in Dry Creek
3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Healdsburg
Pool, hot tub, and pizza oven in wine country
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.88 out of 5 average rating, 33 reviews
Superhost
Home in Healdsburg
Vineyard estate with pool and fire pit
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
Home in Healdsburg
Vineyard views from Montage Healdsburg Resort
4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
New place to stay
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Farm stay in Healdsburg
Vineyard loft on the Miracle Mile
1 king bed, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 690 reviews