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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
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, 254 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
9-acre estate with pool and vineyard views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 85 reviews
Guest favourite
Home in Forestville
Midcentury-modern with 14-foot vaulted ceilings
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 367 reviews
Top guest favourite
Home in Healdsburg
Architect-designed home on a private vineyard
3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 180 reviews
Home in Windsor
Maximalist bungalow with a hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Healdsburg
Vineyard views from a private redwood deck
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Tiny home in Sebastopol
Wine country views with a barrel sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 205 reviews
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Aug
4.88 out of 5 average rating, 66 reviews
Top guest favourite
Guest house in Healdsburg
Vineyard cottage with Russian River views
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 129 reviews
Guest favourite
Home in Healdsburg
Homestead with Pool Hot Tub and Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 100 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 97 reviews
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
Guest house in Healdsburg
Vineyard views and a private hot tub
1 bedroom, 1 king bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 164 reviews
Top guest favourite
Home in Healdsburg
A-frame with pool among towering redwoods
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Farm stay in Healdsburg
Vineyard loft on the Miracle Mile
1 king bed, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 690 reviews
Guest favourite
Home in Healdsburg
Hilltop vineyard views with saltwater pool
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Healdsburg
Vineyard views and a hot tub
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 255 reviews