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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Fitch Mountain
3 bedrooms, 3 beds, 3 shared bathrooms
5–10 Aug
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5.0 out of 5 average rating, 24 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
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
5–10 Aug
4.98 out of 5 average rating, 56 reviews
Top guest favourite
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, 214 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 118 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.98 out of 5 average rating, 182 reviews
Top 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, 361 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
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, 4 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, 43 reviews
Guest favourite
Home in Healdsburg
Bermudes Family Vineyard View Healdsburg House
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.85 out of 5 average rating, 91 reviews
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
4.98 out of 5 average rating, 127 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
9–14 Aug
New place to stay
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Sebastopol
Refined Luxury, Vineyard Views close to Healdsburg
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
2 bedrooms, 2 queen beds, 3 bathrooms
20–25 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Healdsburg
Modern Healdsburg Retreat • Hot Tub, Bocce & Views
3 bedrooms, 3 king beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 177 reviews