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Search results; Over 1,000 places in Healdsburg

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
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
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
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
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
Alexander Valley: Wine Lover and Cycling Paradise
1 bed
May 21 – 26
4.98 out of 5 average rating, 249 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
Home in Healdsburg
10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
3 beds
Jun 23 – 28
5.0 out of 5 average rating, 55 reviews
Guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
Apr 19 – 24
5.0 out of 5 average rating, 15 reviews
Superhost
Villa in Healdsburg
Hilltop Vista Villa
2 king beds
May 6 – 11
4.94 out of 5 average rating, 112 reviews
Guest favorite
Home in Healdsburg
Vineyard views, stunning house & deck
2 beds
May 8 – 13
5.0 out of 5 average rating, 37 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
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 beds
Apr 19 – 24
5.0 out of 5 average rating, 45 reviews
Superhost
Home in Healdsburg
Private Vineyard Haven
3 beds
May 27 – Jun 1
4.9 out of 5 average rating, 29 reviews
Guest favorite
Guesthouse in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 king bed
May 8 – 13
5.0 out of 5 average rating, 102 reviews
Guest favorite
Home in Healdsburg
Vineyards Edge - Pool, Spa, Bikes- 1mi to Downtown
4 beds
May 19 – 24
4.96 out of 5 average rating, 28 reviews
Guest favorite
Home in Healdsburg
Healdsburg House - Chiquita Road
4 beds
Apr 21 – 26
5.0 out of 5 average rating, 39 reviews