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Search results; Over 1,000 homes in Healdsburg

Top guest favorite
Wake to vineyard views at this remodeled Sonoma countryside house with a fire pit
2 bedrooms, 3 beds, 2 private baths
Nov 16 – 21
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4.96 out of 5 average rating, 98 reviews
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
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
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
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
Guest favorite
Dine overlooking a private vineyard at this Healdsburg house with a piano
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 4 beds, 2 baths
Sep 7 – 12
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
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
Guest favorite
This airy Healdsburg home puts you 2 blocks from the Plaza with a patio
4.97 out of 5 average rating, 110 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
This architect-designed Healdsburg home puts you on 10 acres with a vineyard
4.98 out of 5 average rating, 183 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Top guest favorite
Nestled in the trees, this Healdsburg guesthouse gives you a private hot tub and wooded views
4.99 out of 5 average rating, 318 reviews, 1 bedroom, 1 bed, 1 bath
Aug 29 – Sep 3
Top guest favorite
Soak in Dry Creek Valley vineyard views from this house’s hot tub and sauna
4.98 out of 5 average rating, 123 reviews, 2 bedrooms, 4 beds, 3 baths
Aug 22 – 27
Guest favorite
This Sonoma County treehouse puts you in the redwoods with a sauna and cedar hot tub
4.98 out of 5 average rating, 365 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Superhost
Soak in vineyard views from the hot tub at this Healdsburg cottage
4.91 out of 5 average rating, 259 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
Top guest favorite
Wake to gourmet breakfast on your private patio at this 1930s Healdsburg guesthouse
4.95 out of 5 average rating, 213 reviews, 1 bedroom, 1 bed, 1 bath
Oct 11 – 16
Top guest favorite
Soak in vineyard views from the private redwood deck at this 1950s Healdsburg house
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 20 – 25
Top guest favorite
This A-frame in Healdsburg gives you valley views, a hot tub, and a redwood pool
4.92 out of 5 average rating, 50 reviews, 5 bedrooms, 7 beds, 4 baths
Aug 23 – 28
Guest favorite
Soak in the hot tub at this 1880s Healdsburg cottage, 2 blocks from the Plaza
4.9 out of 5 average rating, 93 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 7 – 12
Top guest favorite
This Healdsburg estate gives you 9 acres, vineyard views, and a pool and spa
4.98 out of 5 average rating, 86 reviews, 4 bedrooms, 6 beds, 4 baths
Nov 14 – 19