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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 private bathrooms
6–11 Sept
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4.92 out of 5 average rating, 255 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
5.0 out of 5 average rating, 254 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
5.0 out of 5 average rating, 118 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4.98 out of 5 average rating, 85 reviews, 4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Aug
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Healdsburg
Architect-designed home on a private vineyard
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Superhost
Home in Geyserville
Vineyard estate with pool and winery tastings
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
5.0 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Guest house in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
5.0 out of 5 average rating, 164 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Guest house in Healdsburg
Vineyard cottage with Russian River views
4.99 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Healdsburg
Casa Pavone, by Vinifera Homes
4.88 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Healdsburg
Haven with Pool, Hot Tub and Tastings Included
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
Superhost
Home in Healdsburg
The Grove on Alexander Valley
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
Luxe
Home in Healdsburg
New 2024 build with a saltwater pool
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
Home in Windsor
Maximalist bungalow with a hot tub
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul