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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 bed, 1 private bathroom
18–23 Aug
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4.99 out of 5 average rating, 318 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 261 reviews
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Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 119 reviews
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Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 215 reviews
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Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 51 reviews
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Home in Healdsburg
Healdsburg Luxe Reserve for 8, pool, spa, firepit
3 bedrooms, 4 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
12–17 Aug
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 129 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 363 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in Healdsburg
Wine Country Retreat - Modern Luxury Estate
4 bedrooms, 4 beds, 3.5 bathrooms
26–31 Oct
4.94 out of 5 average rating, 31 reviews
Guest favourite
Home in Santa Rosa
Titan: Theater, Heated Pool, Gym, Billiards
5 bedrooms, 8 beds, 4 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
4.95 out of 5 average rating, 65 reviews
Guest favourite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 bedrooms, 2 beds, 1 bathroom
5–10 Sept
4.92 out of 5 average rating, 132 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 110 reviews