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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 261 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 119 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed
23–28 Aug
5.0 out of 5 average rating, 215 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 254 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 129 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds
10–15 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 364 reviews
Guest favourite
Home in Santa Rosa
Titan: Theater, Heated Pool, Gym, Billiards
5 bedrooms, 8 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds
17–22 Aug
4.97 out of 5 average rating, 237 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds
10–15 Aug
4.96 out of 5 average rating, 83 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds
22–27 Aug
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Luxe Reserve for 8, pool, spa, firepit
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Santa Rosa
Sky View: Heated Pool & Hot Tub, 5 Acres
4 bedrooms, 5 beds
9–14 Sept
4.99 out of 5 average rating, 70 reviews
Top guest favourite
Home in Sebastopol
Refined Luxury, Vineyard Views close to Healdsburg
4 bedrooms, 5 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 17 reviews