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Search results; Over 1,000 homes in Healdsburg

Luxe
Home in Healdsburg
Chalk Hill 360°
4 bedrooms, 4 beds, 3.5 private baths
Aug 26 – 31
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5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 baths
Sep 13 – 18
4.94 out of 5 average rating, 102 reviews
Top guest favorite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 baths
Nov 16 – 21
4.96 out of 5 average rating, 98 reviews
Top guest favorite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 7 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 baths
Aug 13 – 18
Top guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bath
Sep 7 – 12
4.98 out of 5 average rating, 56 reviews
Top guest favorite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
4.98 out of 5 average rating, 183 reviews
Top guest favorite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 baths
Oct 25 – 30
5.0 out of 5 average rating, 263 reviews
Top guest favorite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 baths
Aug 30 – Sep 4
4.98 out of 5 average rating, 64 reviews
Top guest favorite
Guesthouse in Healdsburg
Bunkhouse at Side Road Farm
1 bedroom, 1 queen bed, 1 bath
Aug 30 – Sep 4
4.99 out of 5 average rating, 256 reviews
Guest favorite
Vacation home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bath
Aug 21 – 26
4.96 out of 5 average rating, 83 reviews
Top guest favorite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 baths
Sep 13 – 18
5.0 out of 5 average rating, 72 reviews
Top guest favorite
Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bath
Aug 23 – 28
4.99 out of 5 average rating, 178 reviews
Top guest favorite
Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
4.93 out of 5 average rating, 655 reviews
Top guest favorite
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
2 bedrooms, 3 king beds, 3 baths
Oct 16 – 23
5.0 out of 5 average rating, 117 reviews
Top guest favorite
Home in Healdsburg
Vineyard Vue - Wine Tastings Included
3 bedrooms, 3 beds, 3.5 baths
Oct 26 – 31
4.99 out of 5 average rating, 76 reviews
Top guest favorite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 bath
Aug 24 – 29
4.85 out of 5 average rating, 91 reviews
Guest favorite
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
1 bedroom, 1 queen bed, 1 bath
Nov 8 – 13
4.94 out of 5 average rating, 234 reviews
Top guest favorite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 baths
Aug 15 – 20
4.95 out of 5 average rating, 65 reviews