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Search results; Over 1,000 places in Healdsburg

Guest favorite
Home in Healdsburg
Wine Country Cottage Walkable to River or Downtown
2 beds
Aug 4 – 9
4.96 out of 5 average rating, 146 reviews
Guest favorite
Home in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg
4 beds
Jun 30 – Jul 5
4.98 out of 5 average rating, 52 reviews
Guest favorite
Guesthouse in Healdsburg
Th Roost - Sun Room
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 288 reviews
Guest favorite
Home in Healdsburg
The Dragonfly Healdsburg
3 king beds
May 5 – 10
5.0 out of 5 average rating, 8 reviews
Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
Apr 19 – 24
4.98 out of 5 average rating, 177 reviews
Guest favorite
Home in Healdsburg
Healdsburg Garden House
3 beds
Apr 28 – May 3
4.93 out of 5 average rating, 526 reviews
Guest favorite
Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 king bed
Jul 9 – 14
5.0 out of 5 average rating, 242 reviews
Guest favorite
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bed
May 21 – 26
4.98 out of 5 average rating, 249 reviews
Guest favorite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 queen bed
May 5 – 10
4.92 out of 5 average rating, 411 reviews
Guest favorite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
Jul 29 – Aug 3
4.97 out of 5 average rating, 475 reviews
Guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
Apr 19 – 24
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Healdsburg
Healdsburg Plaza Gem
2 queen beds
Apr 22 – 27
4.9 out of 5 average rating, 62 reviews
Guest favorite
Home in Healdsburg
10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
3 beds
Jun 23 – 28
5.0 out of 5 average rating, 54 reviews
Guest favorite
Guesthouse in Healdsburg
Bucher Vineyard Cottage
1 queen bed
Jun 13 – 18
5.0 out of 5 average rating, 32 reviews
Guest favorite
Home in Healdsburg
Creekside Cottage
2 beds
May 19 – 24
5.0 out of 5 average rating, 18 reviews
Home in Healdsburg
Cypress House & Studio, Walk to Healdsburg Plaza
3 beds
May 12 – 17
4.9 out of 5 average rating, 21 reviews
Guest favorite
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 beds
Apr 21 – 26
5.0 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Healdsburg
Ultra-Modern 2 Bedroom Flat In Downtown Healdsburg
2 beds
Apr 19 – 24
4.98 out of 5 average rating, 66 reviews