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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 21 – 26
Apr 21 – 26
$296
$225
night
$225 per night, originally $296
4.94 out of 5 average rating, 288 reviews
4.94 (288)
Guest favorite
Guest favorite
Home in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg
4 beds
4 beds
Jun 30 – Jul 5
Jun 30 – Jul 5
$1,094
night
$1,094 per night
4.98 out of 5 average rating, 52 reviews
4.98 (52)
Guest favorite
Guest favorite
Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 beds
2 beds
May 19 – 24
May 19 – 24
$255
night
$255 per night
4.94 out of 5 average rating, 72 reviews
4.94 (72)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
$393
$348
night
$348 per night, originally $393
4.98 out of 5 average rating, 177 reviews
4.98 (177)
Guest favorite
Guest favorite
Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 king bed
1 king bed
Jul 9 – 14
Jul 9 – 14
$351
night
$351 per night
5.0 out of 5 average rating, 242 reviews
5.0 (242)
Guest favorite
Guest favorite
Home in Healdsburg
Healdsburg Garden House
3 beds
3 beds
Apr 28 – May 3
Apr 28 – May 3
$179
night
$179 per night
4.93 out of 5 average rating, 526 reviews
4.93 (526)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Bucher Vineyard Cottage
1 queen bed
1 queen bed
Jun 13 – 18
Jun 13 – 18
$268
night
$268 per night
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Guest favorite
Guest favorite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 queen bed
1 queen bed
May 5 – 10
May 5 – 10
$199
night
$199 per night
4.92 out of 5 average rating, 411 reviews
4.92 (411)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bed
1 bed
Jun 27 – Jul 2
Jun 27 – Jul 2
$195
night
$195 per night
4.98 out of 5 average rating, 249 reviews
4.98 (249)
Guest favorite
Guest favorite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
1 king bed
Jul 29 – Aug 3
Jul 29 – Aug 3
$288
night
$288 per night
4.97 out of 5 average rating, 475 reviews
4.97 (475)
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, 55 reviews
5.0 (55)
Guest favorite
Guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
Apr 20 – 25
Apr 20 – 25
$550
night
$550 per night
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Guest favorite
Guest favorite
Home in Healdsburg
Dry Creek Valley Cottage
1 queen bed
1 queen bed
Apr 29 – May 4
Apr 29 – May 4
$185
night
$185 per night
4.96 out of 5 average rating, 430 reviews
4.96 (430)
Guest favorite
Guest favorite
Home in Healdsburg
The Dragonfly Healdsburg
3 king beds
3 king beds
May 5 – 10
May 5 – 10
$656
$552
night
$552 per night, originally $656
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
May 19 – 24
May 19 – 24
$253
night
$253 per night
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Guest favorite
Guest favorite
Home in Healdsburg
Vineyards Edge - Pool, Spa, Bikes- 1mi to Downtown
4 beds
4 beds
May 19 – 24
May 19 – 24
$721
$614
night
$614 per night, originally $721
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Guest favorite
Guest favorite
Vacation home in Healdsburg
Downtown Healdsburg Nest
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$455
night
$455 per night
4.97 out of 5 average rating, 65 reviews
4.97 (65)
Guest favorite
Guest favorite
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$1,316
$1,026
night
$1,026 per night, originally $1,316
5.0 out of 5 average rating, 49 reviews
5.0 (49)
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