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Search results; Over 1,000 homes in Healdsburg

Luxe
Home in Healdsburg
Hilltop 360° views with pool and spa
4 bedrooms, 4 beds, 3.5 private baths
Aug 26 – 31
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5.0 out of 5 average rating, 17 reviews
Top guest favorite
Home in Healdsburg
10-acre vineyard with a hot tub
5.0 out of 5 average rating, 263 reviews, 2 bedrooms, 3 beds, 1.5 baths
Oct 25 – 30
Top guest favorite
Home in Healdsburg
Hot tub on 1.5 acres amid vineyards
5.0 out of 5 average rating, 119 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 24 – 29
Top guest favorite
Apartment in Healdsburg
Top-floor loft in a Quonset Hut
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bath
Sep 7 – 12
Top guest favorite
Home in Healdsburg
Vineyard views, 5-min walk to river
4.93 out of 5 average rating, 655 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Guest favorite
Home in Healdsburg
Vineyard views and alfresco dining
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 2 baths
Sep 7 – 12
Guest favorite
Treehouse in Bodega Bay
Redwood treehouse 30 feet up on a ranch
4.94 out of 5 average rating, 234 reviews, 1 bedroom, 1 bed, 1 bath
Nov 8 – 13
Top guest favorite
Home in Windsor
Bold, maximalist bungalow with a hot tub
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 16 – 21
Guest favorite
Vacation home in Healdsburg
Airy bohemian flat 2 blocks from Plaza
4.97 out of 5 average rating, 110 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
Home in Healdsburg
Private vineyard on 10 acres
4.98 out of 5 average rating, 183 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Top guest favorite
Guesthouse in Healdsburg
Gated cottage with a private hot tub
4.99 out of 5 average rating, 318 reviews, 1 bedroom, 1 bed, 1 bath
Aug 29 – Sep 3
Top guest favorite
Home in Healdsburg
Vineyard views with a private spa
4.98 out of 5 average rating, 123 reviews, 2 bedrooms, 4 beds, 3 baths
Aug 22 – 27
Guest favorite
Treehouse in Occidental
Redwood treehouse with sauna and hot tub
4.98 out of 5 average rating, 365 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Superhost
Cottage in Healdsburg
Vineyard views and a hot tub
4.91 out of 5 average rating, 259 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
Top guest favorite
Guesthouse in Healdsburg
Gourmet breakfast on a private patio
4.95 out of 5 average rating, 213 reviews, 1 bedroom, 1 bed, 1 bath
Oct 11 – 16
Top guest favorite
Home in Healdsburg
Vintage 50s home with vineyard views
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 20 – 25
Top guest favorite
Home in Healdsburg
A-frame with pool among towering redwoods
4.92 out of 5 average rating, 50 reviews, 5 bedrooms, 7 beds, 4 baths
Aug 23 – 28
Guest favorite
Home in Healdsburg
1880s cottage with hot tub and tastings
4.9 out of 5 average rating, 93 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 7 – 12
Top guest favorite
Farm stay in Healdsburg
Vineyard loft on the Miracle Mile
4.97 out of 5 average rating, 701 reviews, 1 bed, 1 bath
Nov 16 – 21