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Search results; Over 1,000 homes in Southold

Top guest favourite

Guest suite in Southold

Comfortable Suite, a walk to the beach

1 bedroom, 1 bed, 1 private bathroom

5–10 Jul

$1,791 SGD for 5 nights

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4.94 out of 5 average rating, 148 reviews

Guest favourite

Flat in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

1 bedroom, 1 queen bed, 1 bathroom

20–25 Jul

$3,994 SGD for 5 nights

4.83 out of 5 average rating, 6 reviews

Top guest favourite

Cottage in Southold

Adorable Cottage

2 bedrooms, 4 queen beds, 1 bathroom

13–18 Sept

$3,010 SGD for 5 nights

4.95 out of 5 average rating, 78 reviews

Top guest favourite

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

3 bedrooms, 5 beds, 2.5 bathrooms

5–11 Jul

5.0 out of 5 average rating, 45 reviews

Guest favourite

Home in Southold

Family and Dog Friendly Private Beach

3 bedrooms, 3 queen beds, 2 bathrooms

25–30 Jul

$5,022 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,376 SGD for 5 nights

4.94 out of 5 average rating, 53 reviews

Guest favourite

Home in Southold

Southold waterfront 4 bed, pool open til October

4 bedrooms, 5 beds, 3 bathrooms

24–29 Jul

$11,810 SGD for 5 nights

4.9 out of 5 average rating, 77 reviews

Guest favourite

Home in Southold

Charming Ranch in North Fork

3 bedrooms, 5 beds, 1 bathroom

27 Jul – 1 Aug

$3,911 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Guest favourite

Flat in Southold

Bright, Southold Studio Apt near beach & town

2 beds, 1 bathroom

12–17 Jul

$2,103 SGD for 5 nights

4.94 out of 5 average rating, 144 reviews

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

4–11 Jul

$10,020 SGD for 7 nights

Guest favourite

Home in Southold

Shelter Bay Cove Waterfront Escape

3 bedrooms, 3 queen beds, 2 bathrooms

5–10 Sept

$5,624 SGD for 5 nights

4.97 out of 5 average rating, 30 reviews

Top guest favourite

Home in Southold

NoFo Family Beach House — Walk To Private Beach

4 bedrooms, 4 beds, 2 bathrooms

16–23 Aug

$6,647 SGD for 7 nights

5.0 out of 5 average rating, 32 reviews

Superhost

Home in Southold

Sunset Cottage

3 bedrooms, 4 beds, 2.5 bathrooms

14–21 Jul

$8,986 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Southold

Dockside Getaway in Southold NY

3 bedrooms, 5 beds, 3 bathrooms

6–11 Jul

$7,883 SGD for 5 nights

4.95 out of 5 average rating, 40 reviews

Guest favourite

Cottage in Southold

Cozy Cottage on the Great Pond near beach.

2 bedrooms, 3 beds, 1.5 bathrooms

27 Jul – 1 Aug

$2,618 SGD for 5 nights

4.9 out of 5 average rating, 196 reviews

Guest favourite

Home in Southold

Southold Sea'renity

3 bedrooms, 5 beds, 2 bathrooms

30 Jul – 4 Aug

$5,761 SGD for 5 nights

4.82 out of 5 average rating, 45 reviews

Top guest favourite

Home in Southold

Private Waterfront home with Dock!

4 bedrooms, 5 beds, 2.5 bathrooms

10–15 Jul

$8,039 SGD for 5 nights

5.0 out of 5 average rating, 18 reviews

Superhost

Flat in Cutchogue

Cozy North Fork Hideaway

1 bedroom, 1 bed, 1 bathroom

5–10 Jul

$2,430 SGD for 5 nights

New place to stay

Top guest favourite

Home in East Marion

Private North Fork Cottage- Walk to Beach!

3 bedrooms, 4 beds, 2 bathrooms

16–21 Jul

$3,917 SGD for 5 nights

4.9 out of 5 average rating, 41 reviews