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Search results; Over 1,000 homes in Healdsburg

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 private bathroom
27 Jul – 1 Aug
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4.97 out of 5 average rating, 251 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
Hot tub on 1.5 acres amid vineyards
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
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Healdsburg
Top-floor loft in a Quonset Hut
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Luxe
Home in Healdsburg
Dry Creek Wonderland | Private Farm Estate in Wine
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Superhost
Home in Healdsburg
Vineyard villa with pool and wine tastings
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
19–24 Jul
Top guest favourite
Tiny home in Sebastopol
Wine country views with a barrel sauna
5.0 out of 5 average rating, 205 reviews, 1 bedroom, 1 bed, 1 bathroom
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
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
Home in Geyserville
Vineyard home with a spa in Dry Creek
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Guest favourite
Villa in Healdsburg
Heated pool and vineyard views near downtown
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Luxe
Home in Healdsburg
Luxurious 3-Bedroom Home in Healdsburg
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Healdsburg
Private vineyard with complimentary winery tastings
4.88 out of 5 average rating, 66 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
Guest favourite
Home in Healdsburg
Pool, hot tub, and pizza oven in wine country
4.88 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Treehouse in Bodega Bay
Redwood treehouse 30 feet up on a ranch
4.96 out of 5 average rating, 225 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Oct
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
4.97 out of 5 average rating, 690 reviews, 1 bed, 1 bathroom
27 Oct – 1 Nov