Search results; Over 1,000 places in Healdsburg

Prices include all fees
Top guest favorite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
Free cancellation
Oct 19 – 24
ﺩ.ﺇ8,769 for 5 nights
for 5 nights
5.0 out of 5 average rating, 162 reviews
Top guest favorite
Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
Free cancellation
Jul 25 – 30
ﺩ.ﺇ8,658 for 5 nights
for 5 nights
4.99 out of 5 average rating, 278 reviews
Top guest favorite
Guesthouse in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 king bed
Jun 1 – 6
ﺩ.ﺇ11,408 for 5 nights
for 5 nights
5.0 out of 5 average rating, 133 reviews
Top guest favorite
Home in Healdsburg
Healdsburg Plaza Charmer w/ Hot Tub
3 beds
Jun 14 – 19
ﺩ.ﺇ13,995 for 5 nights, originally ﺩ.ﺇ15,892
for 5 nights
5.0 out of 5 average rating, 29 reviews
Top guest favorite
Home in Healdsburg
Healdsburg House - Chiquita Road
Free cancellation
Jun 15 – 20
ﺩ.ﺇ18,162 for 5 nights, originally ﺩ.ﺇ21,949
for 5 nights
5.0 out of 5 average rating, 75 reviews
Top guest favorite
Home in Healdsburg
Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger
4 beds
Jun 7 – 12
ﺩ.ﺇ20,655 for 5 nights, originally ﺩ.ﺇ24,902
for 5 nights
4.99 out of 5 average rating, 94 reviews
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More stays available for your dates

Luxe
Home in Healdsburg
Mill Creek - AvantStay | Patio, Hot Tub, A+ Design
3 beds
Jun 9 – 14
ﺩ.ﺇ9,767 for 5 nights
for 5 nights
4.88 out of 5 average rating, 17 reviews
Top guest favorite
Cottage in Healdsburg
Bee Haven Cottage
1 queen bed
Jul 7 – 12
ﺩ.ﺇ6,801 for 5 nights
for 5 nights
5.0 out of 5 average rating, 194 reviews
Top guest favorite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 queen bed
Jun 15 – 20
ﺩ.ﺇ6,027 for 5 nights
for 5 nights
4.98 out of 5 average rating, 43 reviews
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
3 beds
Jun 28 – Jul 3
ﺩ.ﺇ9,741 for 5 nights, originally ﺩ.ﺇ10,900
for 5 nights
4.93 out of 5 average rating, 177 reviews
Guest favorite
Home in Healdsburg
Pet-Friendly Homestead w/ Pool & Hot Tub
4 beds
Jun 1 – 6
ﺩ.ﺇ14,658 for 5 nights, originally ﺩ.ﺇ19,682
for 5 nights
4.97 out of 5 average rating, 68 reviews
Top guest favorite
Home in Healdsburg
Healdsburg Vineyard Home - 3BD + Den, Spa, Bocce
4 beds
Jun 11 – 16
ﺩ.ﺇ13,118 for 5 nights, originally ﺩ.ﺇ15,004
for 5 nights
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Healdsburg
Private Vineyard Haven
2 king beds
Jun 14 – 19
ﺩ.ﺇ20,599 for 5 nights
for 5 nights
4.91 out of 5 average rating, 43 reviews
Superhost
Home in Healdsburg
Pet Friendly with Hot Tub. Pool Heat Avail!
4 beds
Jun 1 – 6
ﺩ.ﺇ15,003 for 5 nights
for 5 nights
4.88 out of 5 average rating, 16 reviews
Guest favorite
Home in Healdsburg
Vineyard views, stunning house & deck
3 beds
Jul 9 – 14
ﺩ.ﺇ10,753 for 5 nights, originally ﺩ.ﺇ13,615
for 5 nights
4.97 out of 5 average rating, 79 reviews
Top guest favorite
Guesthouse in Healdsburg
Private 1-bedroom guesthouse with great amenities
Free cancellation
Jun 1 – 6
ﺩ.ﺇ11,236 for 5 nights
for 5 nights
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Healdsburg
Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool
Free cancellation
Jun 30 – Jul 5
ﺩ.ﺇ13,194 for 5 nights, originally ﺩ.ﺇ18,148
for 5 nights
4.92 out of 5 average rating, 76 reviews
Superhost
Villa in Healdsburg
Hilltop Healdsburg Villa | Pool & Breakfast
Free cancellation
Jun 8 – 13
ﺩ.ﺇ17,960 for 5 nights
for 5 nights
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