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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, 146 reviews

Flat in Southold

1BR Apartment - Beach Access - Wineries, Vineyards

1 bedroom, 1 queen bed, 1 bathroom

5–10 Jul

$2,346 SGD for 5 nights

New place to stay

Flat in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

1 bedroom, 1 queen bed, 1 bathroom

20–25 Jul

$3,973 SGD for 5 nights

5.0 out of 5 average rating, 4 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

Top guest favourite

Home in Southold

NoFo Family Beach House — Walk To Private Beach

4 bedrooms, 4 beds, 2 bathrooms

13–20 Jul

$6,246 SGD for 7 nights

5.0 out of 5 average rating, 32 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

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

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

1–8 Jul

$10,388 SGD for 7 nights

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

Top guest favourite

Home in Southold

Dockside Getaway in Southold NY

3 bedrooms, 5 beds, 3 bathrooms

3–8 Jul

$8,703 SGD for 5 nights

4.95 out of 5 average rating, 40 reviews

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

13–20 Jul

$21,942 SGD for 7 nights

Free cancellation

4.94 out of 5 average rating, 32 reviews

Guest favourite

Home in Southold

Southold Sea'renity

3 bedrooms, 5 beds, 2 bathrooms

30 Jul – 4 Aug

$5,760 SGD for 5 nights

4.82 out of 5 average rating, 45 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, 77 reviews

Top guest favourite

Home in Southold

Charming Ranch in North Fork

3 bedrooms, 5 beds, 1 bathroom

18–23 Jul

$3,911 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Home in Southold

Luxury North Fork Beachfront Escape Near Greenport

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$9,905 SGD for 5 nights

4.93 out of 5 average rating, 15 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

Guest favourite

Home in Southold

Peconic Pearl Cottage

4 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,770 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Southold

Waterfront Beach House with Plunge Pool & Hot Tub

4 bedrooms, 7 beds, 4.5 bathrooms

19–26 Jul

4.97 out of 5 average rating, 39 reviews

Guest favourite

Home in Southold

Shelter Bay Cove Waterfront Escape

3 bedrooms, 3 queen beds, 2 bathrooms

5–12 Sept

$6,796 SGD for 7 nights

4.97 out of 5 average rating, 30 reviews