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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
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4.99 out of 5 average rating, 318 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 57 reviews
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Guest suite in Healdsburg
Luxury One Bedroom Garden and Poolside Suite
1 bedroom, 1 king bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 50 reviews
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Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 167 reviews
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Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
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, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 219 reviews
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, 368 reviews
Superhost
Treehouse in Bodega Bay
Eagle's Nest Treehouse Farm Stay
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.94 out of 5 average rating, 234 reviews
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Cottage in Geyserville
Country Carriage House in Downtown Geyserville
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 178 reviews
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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, 263 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Hideaway
2 bedrooms, 2 beds, 1 bathroom
21–26 Aug
4.96 out of 5 average rating, 83 reviews
Top guest favourite
Guest suite in Forestville
Cozy & Sweet Redwood Retreat
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 88 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 bathroom
10–15 Sept
4.98 out of 5 average rating, 326 reviews
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Guest house in Healdsburg
The Roost - Sun Room
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 371 reviews
Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 480 reviews
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Home in Healdsburg
Healdsburg Garden House
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 655 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Plaza Pet-Friendly Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.99 out of 5 average rating, 72 reviews