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Search results; 745 places in Healdsburg
745 places in Healdsburg
Top guest favorite
Guest favorite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
Free cancellation
Free cancellation
Aug 31 – Sep 5
Aug 31 – Sep 5
ﺩ.ﺇ9,277
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ﺩ.ﺇ9,277 for 5 nights
for 5 nights
5.0 out of 5 average rating, 157 reviews
5.0 (157)
Top guest favorite
Guest favorite
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
1 queen bed
1 queen bed
May 18 – 23
May 18 – 23
ﺩ.ﺇ6,178
ﺩ.ﺇ5,304
Show price breakdown
ﺩ.ﺇ5,304 for 5 nights, originally ﺩ.ﺇ6,178
for 5 nights
4.93 out of 5 average rating, 332 reviews
4.93 (332)
Top guest favorite
Guest favorite
Guesthouse in Healdsburg
Bucher Vineyard Cottage
1 queen bed
1 queen bed
Jun 21 – 26
Jun 21 – 26
ﺩ.ﺇ6,160
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ﺩ.ﺇ6,160 for 5 nights
for 5 nights
4.99 out of 5 average rating, 85 reviews
4.99 (85)
Luxe
Luxe
Home in Healdsburg
Mill Creek - AvantStay | Patio, Hot Tub, A+ Design
3 beds
3 beds
May 18 – 23
May 18 – 23
ﺩ.ﺇ7,739
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ﺩ.ﺇ7,739 for 5 nights
for 5 nights
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Top guest favorite
Guest favorite
Home in Healdsburg
Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger
4 beds
4 beds
May 12 – 17
May 12 – 17
ﺩ.ﺇ21,737
ﺩ.ﺇ16,983
Show price breakdown
ﺩ.ﺇ16,983 for 5 nights, originally ﺩ.ﺇ21,737
for 5 nights
4.99 out of 5 average rating, 92 reviews
4.99 (92)
Guest favorite
Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
1 queen bed
May 11 – 16
May 11 – 16
ﺩ.ﺇ8,524
ﺩ.ﺇ7,547
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ﺩ.ﺇ7,547 for 5 nights, originally ﺩ.ﺇ8,524
for 5 nights
4.97 out of 5 average rating, 202 reviews
4.97 (202)
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Top guest favorite
Guest favorite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
1 king bed
Jun 11 – 16
Jun 11 – 16
ﺩ.ﺇ5,261
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ﺩ.ﺇ5,261 for 5 nights
for 5 nights
4.97 out of 5 average rating, 575 reviews
4.97 (575)
Top guest favorite
Guest favorite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
Free cancellation
Free cancellation
May 26 – 31
May 26 – 31
ﺩ.ﺇ10,298
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ﺩ.ﺇ10,298 for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
3 beds
3 beds
May 18 – 23
May 18 – 23
ﺩ.ﺇ5,993
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ﺩ.ﺇ5,993 for 5 nights
for 5 nights
4.93 out of 5 average rating, 176 reviews
4.93 (176)
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Guest favorite
Guest favorite
Home in Healdsburg
Healdsburg Plaza Charmer w/ Hot Tub
3 beds
3 beds
Jun 1 – 6
Jun 1 – 6
ﺩ.ﺇ14,043
ﺩ.ﺇ11,748
Show price breakdown
ﺩ.ﺇ11,748 for 5 nights, originally ﺩ.ﺇ14,043
for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favorite
Guest favorite
Guesthouse in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 king bed
1 king bed
May 27 – Jun 1
May 27 – Jun 1
ﺩ.ﺇ11,839
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ﺩ.ﺇ11,839 for 5 nights
for 5 nights
5.0 out of 5 average rating, 132 reviews
5.0 (132)
Guest favorite
Guest favorite
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
3 king beds
3 king beds
May 27 – Jun 1
May 27 – Jun 1
ﺩ.ﺇ17,865
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ﺩ.ﺇ17,865 for 5 nights
for 5 nights
5.0 out of 5 average rating, 90 reviews
5.0 (90)
Top guest favorite
Guest favorite
Home in Healdsburg
The Dragonfly Healdsburg
3 king beds
3 king beds
May 12 – 17
May 12 – 17
ﺩ.ﺇ16,764
ﺩ.ﺇ14,246
Show price breakdown
ﺩ.ﺇ14,246 for 5 nights, originally ﺩ.ﺇ16,764
for 5 nights
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Guest favorite
Guest favorite
Home in Healdsburg
Vineyards Edge: Pool, Spa, 1G, Bikes- 1m to town
4 beds
4 beds
May 18 – 23
May 18 – 23
ﺩ.ﺇ14,227
ﺩ.ﺇ9,820
Show price breakdown
ﺩ.ﺇ9,820 for 5 nights, originally ﺩ.ﺇ14,227
for 5 nights
4.94 out of 5 average rating, 86 reviews
4.94 (86)
Top guest favorite
Guest favorite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 beds
4 beds
May 26 – 31
May 26 – 31
ﺩ.ﺇ13,483
ﺩ.ﺇ10,701
Show price breakdown
ﺩ.ﺇ10,701 for 5 nights, originally ﺩ.ﺇ13,483
for 5 nights
4.84 out of 5 average rating, 117 reviews
4.84 (117)
Top guest favorite
Guest favorite
Home in Healdsburg
Healdsburg Vineyard Home - 3BD + Den, Spa, Bocce
4 beds
4 beds
Jun 11 – 16
Jun 11 – 16
ﺩ.ﺇ15,611
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ﺩ.ﺇ15,611 for 5 nights
for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Superhost
Superhost
Home in Healdsburg
Private Vineyard Haven
2 king beds
2 king beds
May 24 – 29
May 24 – 29
ﺩ.ﺇ19,682
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ﺩ.ﺇ19,682 for 5 nights
for 5 nights
4.91 out of 5 average rating, 43 reviews
4.91 (43)
Guest favorite
Guest favorite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy - Views-Hot Tub
4 beds
4 beds
May 11 – 16
May 11 – 16
ﺩ.ﺇ21,200
ﺩ.ﺇ18,012
Show price breakdown
ﺩ.ﺇ18,012 for 5 nights, originally ﺩ.ﺇ21,200
for 5 nights
4.8 out of 5 average rating, 15 reviews
4.8 (15)
Guest favorite
Guest favorite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
4 beds
4 beds
May 19 – 24
May 19 – 24
ﺩ.ﺇ29,811
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ﺩ.ﺇ29,811 for 5 nights
for 5 nights
5.0 out of 5 average rating, 51 reviews
5.0 (51)
Superhost
Superhost
Home in Healdsburg
Peaceful location, hot tub, fire pit, game room!
Free cancellation
Free cancellation
May 27 – Jun 1
May 27 – Jun 1
ﺩ.ﺇ10,999
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ﺩ.ﺇ10,999 for 5 nights
for 5 nights
4.89 out of 5 average rating, 325 reviews
4.89 (325)
Guest favorite
Guest favorite
Home in Healdsburg
The Wine Ranch
Free cancellation
Free cancellation
Jul 5 – 10
Jul 5 – 10
ﺩ.ﺇ10,117
Show price breakdown
ﺩ.ﺇ10,117 for 5 nights
for 5 nights
4.92 out of 5 average rating, 260 reviews
4.92 (260)
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