Search results; 745 places in Healdsburg

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