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Search results; Over 1,000 homes in Healdsburg

Top guest favourite

Cottage in Healdsburg

Vineyard views close to town w/ free EV charger

1 bedroom, 1 bed, 1 private bathroom

21–26 Jul

$3,144 SGD for 5 nights

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4.96 out of 5 average rating, 68 reviews

Top guest favourite

Home in Healdsburg

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

2 bedrooms, 3 queen beds, 1.5 bathrooms

25–30 Oct

$3,072 SGD for 5 nights

5.0 out of 5 average rating, 254 reviews

Top guest favourite

Home in Healdsburg

Healdsburg House - Chiquita Road

3 bedrooms, 4 beds, 3 bathrooms

24–29 Aug

$5,933 SGD for 5 nights

5.0 out of 5 average rating, 118 reviews

Top guest favourite

Flat in Healdsburg

Downtown Healdsburg Perch

1 bedroom, 1 bed, 1 bathroom

21–26 Jul

$4,411 SGD for 5 nights

4.98 out of 5 average rating, 55 reviews

Top guest favourite

Home in Healdsburg

Wine Country Estate: Pool, Spa & Vineyard Views

4 bedrooms, 6 beds, 4 bathrooms

21–26 Oct

$7,588 SGD for 5 nights

4.98 out of 5 average rating, 85 reviews

Home in St. Helena

Hidden Hills Napa Retreat | St. Helena Gem

4 bedrooms, 6 beds, 5 bathrooms

20–25 Jul

New place to stay

Top guest favourite

Home in Healdsburg

Wake Up in Your Own Private Vineyard - Healdsburg

3 bedrooms, 4 beds, 2 bathrooms

17–22 Jul

$6,836 SGD for 5 nights

4.98 out of 5 average rating, 181 reviews

Superhost

Home in Healdsburg

Vineyard Daydream - Villa with Wine Tastings Inclu

4 bedrooms, 8 beds, 5 bathrooms

19–24 Jul

$15,103 SGD for 5 nights

New place to stay

Home in Windsor

The Gilded Bungalow • walk to town green • hot tub

3 bedrooms, 3 beds, 2.5 bathrooms

25–30 Jul

$4,218 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Healdsburg

Luxury Retreat w/ Pool, Hot Tub & Sauna

3 bedrooms, 4 beds, 3 bathrooms

10–15 Aug

$13,645 SGD for 5 nights

4.99 out of 5 average rating, 126 reviews

Top guest favourite

Home in Healdsburg

Vintage Retreat with Spa in Healdsburg

3 bedrooms, 3 queen beds, 2 bathrooms

23–28 Aug

$2,948 SGD for 5 nights

4.98 out of 5 average rating, 41 reviews

Guest favourite

Villa in Healdsburg

Hilltop Villa with Sweeping Views & Trail Access

2 bedrooms, 2 king beds, 2 bathrooms

19–24 Jul

$3,004 SGD for 5 nights

4.94 out of 5 average rating, 195 reviews

Top guest favourite

Home in Healdsburg

Vineyard Vista, Modern Farmhouse Cottage with Pool

3 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$4,524 SGD for 5 nights

4.92 out of 5 average rating, 131 reviews

Guest favourite

Home in Healdsburg

Casa Pavone, by Vinifera Homes

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$4,064 SGD for 5 nights

4.88 out of 5 average rating, 34 reviews

Luxe

Villa in Healdsburg

New! The Quails Crossing- Healdsburg Vineyard Home

4 bedrooms, 4 beds, 4.5 bathrooms

25–30 Aug

$14,660 SGD for 5 nights

5.0 out of 5 average rating, 94 reviews

Guest favourite

Home in Forestville

Somms Rest Designed Curated Peaceful

3 bedrooms, 3 beds, 2 bathrooms

3–8 Oct

$1,750 SGD for 5 nights

4.99 out of 5 average rating, 368 reviews

Top guest favourite

Home in Healdsburg

Private Oasis in Healdsburg: Pool, Spa & Views

6 bedrooms, 7 beds, 3.5 bathrooms

26–31 Jul

$9,680 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Guest favourite

Tiny home in Sebastopol

The Sonoma Spyglass | Incredible Views + Sauna

1 bedroom, 1 bed, 1 bathroom

23–28 Aug

5.0 out of 5 average rating, 206 reviews

Top guest favourite

Guest suite in Healdsburg

Jimtown Luxury Suite

1 bedroom, 1 king bed, 1 bathroom

17–22 Jul

$2,388 SGD for 5 nights

5.0 out of 5 average rating, 95 reviews