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Search results; Over 1,000 places in Healdsburg
Over 1,000 places in Healdsburg
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Th Roost - Sun Room
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$239
night
$239 per night
4.94 out of 5 average rating, 285 reviews
4.94 (285)
Guest favorite
Guest favorite
Home in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg
4 beds
4 beds
Jun 2 – 7
Jun 2 – 7
$805
night
$805 per night
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Bucher Vineyard Cottage
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$275
$235
night
$235 per night, originally $275
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Superhost
Superhost
Villa in Healdsburg
Hilltop Vista Villa
2 king beds
2 king beds
Apr 1 – 6
Apr 1 – 6
$365
night
$365 per night
4.94 out of 5 average rating, 108 reviews
4.94 (108)
Guest favorite
Guest favorite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
1 king bed
Jun 8 – 13
Jun 8 – 13
$244
night
$244 per night
4.97 out of 5 average rating, 470 reviews
4.97 (470)
Guest favorite
Guest favorite
Home in Healdsburg
Vineyard views, stunning house & deck
2 beds
2 beds
May 5 – 10
May 5 – 10
$523
$392
night
$392 per night, originally $523
5.0 out of 5 average rating, 36 reviews
5.0 (36)
Guest favorite
Guest favorite
Home in Healdsburg
10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
3 beds
3 beds
Jun 23 – 28
Jun 23 – 28
$426
night
$426 per night
5.0 out of 5 average rating, 49 reviews
5.0 (49)
Guest favorite
Guest favorite
Home in Healdsburg
Vineyard Modern Barn House - Dry Creek Valley
2 king beds
2 king beds
Apr 6 – 11
Apr 6 – 11
$455
night
$455 per night
4.98 out of 5 average rating, 393 reviews
4.98 (393)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$406
night
$406 per night
4.98 out of 5 average rating, 177 reviews
4.98 (177)
Guest favorite
Guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
1 bed
1 bed
Apr 8 – 13
Apr 8 – 13
$550
night
$550 per night
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favorite
Guest favorite
Home in Healdsburg
The Dragonfly Healdsburg
3 king beds
3 king beds
May 5 – 10
May 5 – 10
$705
night
$705 per night
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favorite
Guest favorite
Home in Healdsburg
Creekside Cottage
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$251
night
$251 per night
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Guest favorite
Guest favorite
Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 king bed
1 king bed
Jul 3 – 8
Jul 3 – 8
$396
night
$396 per night
5.0 out of 5 average rating, 241 reviews
5.0 (241)
Guest favorite
Guest favorite
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
3 king beds
3 king beds
Apr 1 – 6
Apr 1 – 6
$665
$531
night
$531 per night, originally $665
5.0 out of 5 average rating, 75 reviews
5.0 (75)
Guest favorite
Guest favorite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$856
$710
night
$710 per night, originally $856
5.0 out of 5 average rating, 45 reviews
5.0 (45)
Guest favorite
Guest favorite
Home in Healdsburg
Vineyard View Retreat 8 Minutes to Healdsburg
6 beds
6 beds
Apr 15 – 20
Apr 15 – 20
$675
night
$675 per night
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favorite
Guest favorite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
4 beds
4 beds
Apr 13 – 18
Apr 13 – 18
$1,095
night
$1,095 per night
5.0 out of 5 average rating, 31 reviews
5.0 (31)
Guest favorite
Guest favorite
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$1,645
$1,316
night
$1,316 per night, originally $1,645
5.0 out of 5 average rating, 45 reviews
5.0 (45)
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