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Search results; Over 1,000 homes in Healdsburg

Top guest favorite
This architect-designed Healdsburg home puts you on 10 acres with a vineyard
3 bedrooms, 4 beds, 2 private baths
Aug 22 – 27
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4.98 out of 5 average rating, 183 reviews
Guest favorite
This Dry Creek Valley farmhouse gives you a pool, hot tub, and winery tastings
4.94 out of 5 average rating, 102 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 13 – 18
Top guest favorite
Wake to vineyard views at this remodeled Sonoma countryside house with a fire pit
4.96 out of 5 average rating, 98 reviews, 2 bedrooms, 3 beds, 2 baths
Nov 16 – 21
Top guest favorite
Bold maximalist decor and a hot tub greet you at this Windsor bungalow
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 16 – 21
This Healdsburg house gives you Fitch Mountain views and full Montage Resort access
4 bedrooms, 4 beds, 4 baths
Aug 13 – 18
Top guest favorite
This top-floor Healdsburg apartment puts you above main street in an arched Quonset hut
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bath
Sep 7 – 12
Top guest favorite
This Healdsburg cottage sits you among 10 acres of vines, a hot tub, and bocce court
5.0 out of 5 average rating, 263 reviews, 2 bedrooms, 3 beds, 1.5 baths
Oct 25 – 30
Top guest favorite
Vineyard views, a pool, and complimentary tastings await you at this Healdsburg villa
4.98 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 2.5 baths
Aug 30 – Sep 4
Top guest favorite
This 1949 guesthouse puts you on a 3-acre Healdsburg farm near wineries
4.99 out of 5 average rating, 256 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Guest favorite
This sleek downtown Healdsburg home puts you 2 blocks from the Plaza
4.96 out of 5 average rating, 83 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 21 – 26
Top guest favorite
Vineyard views, a hot tub, and fire pit greet you at this Healdsburg home
5.0 out of 5 average rating, 72 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 13 – 18
Top guest favorite
This remodeled 1950s tractor barn gives you 6 acres in Geyserville wine country
4.99 out of 5 average rating, 178 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Vineyard and mountain views greet you at this Healdsburg house with a redwood deck
4.93 out of 5 average rating, 655 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Top guest favorite
This secluded Healdsburg cottage on Dry Creek gives you a huge deck and fire pit
5.0 out of 5 average rating, 117 reviews, 2 bedrooms, 3 beds, 3 baths
Oct 16 – 23
Top guest favorite
Vineyard views greet you from the wraparound porch of this Healdsburg farmhouse
4.99 out of 5 average rating, 76 reviews, 3 bedrooms, 3 beds, 3.5 baths
Oct 26 – 31
Top guest favorite
Vineyards surround you at this Windsor cottage with a fire pit and cedar pergola
4.85 out of 5 average rating, 91 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29
Guest favorite
This Bodega Bay treehouse nestles you 30 feet up in ancient redwoods
4.94 out of 5 average rating, 234 reviews, 1 bedroom, 1 bed, 1 bath
Nov 8 – 13
Top guest favorite
Wake to vineyard views at this Healdsburg house with a hot tub and game room
4.95 out of 5 average rating, 65 reviews, 4 bedrooms, 5 beds, 4 baths
Aug 15 – 20
Top guest favorite
Vineyards and oak trees surround you at this Healdsburg house on 1.5 private acres
5.0 out of 5 average rating, 119 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 24 – 29