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Search results; Over 1,000 homes in Healdsburg

Top guest favourite

Guest house in Healdsburg

Luxe Guest Suite in Dry Creek 5 mins From Town!

1 bedroom, 1 bed, 1 private bathroom

25–30 Aug

$4,180 SGD for 5 nights

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5.0 out of 5 average rating, 167 reviews

Guest favourite

Home in Healdsburg

Spacious Healdsburg Home - Walk to the Square!

3 bedrooms, 3 beds

1–6 Aug

$2,921 SGD for 5 nights

5.0 out of 5 average rating, 53 reviews

Top guest favourite

Guest house in Healdsburg

Alexander Valley: Wine Lover and Cycling Paradise

1 bedroom, 3 beds

19–24 Aug

4.98 out of 5 average rating, 324 reviews

Guest favourite

Place to stay in Healdsburg

Modern Vineyard Farmhouse - Zinfandel Room

1 bedroom, 1 bed

1–6 Aug

$2,014 SGD for 5 nights

4.98 out of 5 average rating, 41 reviews

Top guest favourite

Flat in Healdsburg

Downtown Healdsburg Perch

1 bedroom, 1 bed

3–8 Aug

$4,435 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 56 reviews

Guest favourite

Room in Healdsburg

Italian Room · Healdsburg Stay · Breakfast

1 bed

17–22 Aug

$1,844 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Guest house in Healdsburg

Designer Cottage | Garden Oasis | Walk to Plaza

1 bedroom, 1 queen bed

23–28 Aug

$2,361 SGD for 5 nights

Book early to save

4.97 out of 5 average rating, 253 reviews

Top guest favourite

Home in Healdsburg

Dry Creek Valley Cottage

1 bedroom, 1 queen bed

30 Aug – 4 Sept

$1,419 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 490 reviews

Top guest favourite

Guest house in Healdsburg

The Roost - Garden Studio

1 bedroom, 1 bed

2–7 Aug

$1,969 SGD for 5 nights

5.0 out of 5 average rating, 67 reviews

Home in Healdsburg

Great outdoor space, fire pit & gourmet kitchen

1 bedroom, 1 queen bed

21–28 Nov

$3,078 SGD for 7 nights

Top guest favourite

Home in Healdsburg

Vineyard views, hot tub, sauna, cinema

2 bedrooms, 4 beds

1–6 Aug

Extended stay discount

4.98 out of 5 average rating, 121 reviews

Top guest favourite

Guest suite in Healdsburg

Jimtown Luxury Suite

1 bedroom, 1 king bed

27 Aug – 1 Sept

$2,615 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 95 reviews

Top guest favourite

Holiday home in Healdsburg

Downtown Healdsburg Hideaway

2 bedrooms, 2 beds

8–13 Aug

$3,800 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 82 reviews

Top guest favourite

Home in Healdsburg

Vintage Retreat with Spa in Healdsburg

3 bedrooms, 3 queen beds

23–28 Aug

$2,939 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 42 reviews

Top guest favourite

Guest suite in Healdsburg

Luxury One Bedroom Garden and Poolside Suite

1 bedroom, 1 king bed

1–6 Aug

$2,702 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 49 reviews

Top guest favourite

Home in Healdsburg

Healdsburg Garden House

3 bedrooms, 4 beds

2–7 Aug

4.93 out of 5 average rating, 653 reviews

Top guest favourite

Flat in Healdsburg

Bucher Vineyard Studio

1 bedroom, 1 queen bed

9–14 Aug

$1,475 SGD for 5 nights

4.99 out of 5 average rating, 129 reviews

Guest favourite

Farm stay in Healdsburg

Eco Modern Casita in the Vineyards

1 bedroom, 1 queen bed

10–15 Aug

$1,786 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 100 reviews

Top guest favourite

Guest suite in Healdsburg

Pony Ranch Vineyard Estate with Pool

1 bedroom, 1 queen bed

16–21 Aug

$1,544 SGD for 5 nights

4.93 out of 5 average rating, 475 reviews