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Search results; Over 1,000 homes in Healdsburg

Top guest favorite
Home in Healdsburg
Vineyard-surrounded cottage with high ceilings
1 bedroom, 1 bed, 1 private bath
Aug 30 – Sep 4
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4.96 out of 5 average rating, 492 reviews
Guest favorite
Home in Healdsburg
Farmhouse with pool and winery tastings
4.94 out of 5 average rating, 102 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 13 – 18
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 and a fire pit
4.96 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 2 baths
Nov 16 – 21
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
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 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
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
Home in Healdsburg
Vineyard views from Montage Healdsburg Resort
4 bedrooms, 4 beds, 4 baths
Aug 13 – 18
Top guest favorite
Home in Healdsburg
Pool, hot tub, and complimentary winery tastings
4.98 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2.5 baths
Aug 30 – Sep 4
Top guest favorite
Cottage in Geyserville
Remodeled 1950s tractor barn on 6 acres
4.99 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Room in Windsor
Wine Country home with a hot tub
4.93 out of 5 average rating, 167 reviews, 1 queen bed, 1 bath
Aug 16 – 21
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
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
Top guest favorite
Home in Healdsburg
Vineyard views, hot tub, and fire pit
5.0 out of 5 average rating, 72 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 13 – 18
Top guest favorite
Guesthouse in Healdsburg
1949 farmstead, walk to 3 wineries
4.99 out of 5 average rating, 256 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
Home in Healdsburg
Renovated cottage in vineyard-adjacent neighborhood
4.92 out of 5 average rating, 152 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in Healdsburg
Modern farmhouse with complimentary wine tastings
4.99 out of 5 average rating, 76 reviews, 3 bedrooms, 3 beds, 3.5 baths
Oct 26 – 31
Top guest favorite
Cottage in Healdsburg
Secluded modern retreat on Dry Creek
5.0 out of 5 average rating, 117 reviews, 2 bedrooms, 3 beds, 3 baths
Oct 16 – 23