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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

$1,798 SGD for 5 nights

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4.94 out of 5 average rating, 146 reviews

Flat in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

1 bedroom, 1 queen bed, 1 bathroom

5–10 Jul

$3,226 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Southold

Southold Sea'renity

3 bedrooms, 5 beds, 2 bathrooms

30 Jul – 4 Aug

$5,782 SGD for 5 nights

4.82 out of 5 average rating, 45 reviews

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

1–8 Jul

$10,427 SGD for 7 nights

Guest favourite

Home in Southold

Southold waterfront 4 bed, pool open til October

4 bedrooms, 5 beds, 3 bathrooms

24–29 Jul

$11,854 SGD for 5 nights

4.9 out of 5 average rating, 77 reviews

Top guest favourite

Home in Southold

NoFo Family Beach House — Walk To Private Beach

4 bedrooms, 4 beds, 2 bathrooms

13–20 Jul

$6,347 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 32 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,400 SGD for 5 nights

4.94 out of 5 average rating, 53 reviews

Guest favourite

Guest house in Southold

Southold- Adorable 1 Bedroom Cottage

1 bedroom, 1 queen bed, 1 bathroom

16–21 Jul

4.9 out of 5 average rating, 79 reviews

Guest favourite

Flat in Southold

Bright, Southold Studio Apt near beach & town

2 beds, 1 bathroom

12–17 Jul

$2,111 SGD for 5 nights

4.94 out of 5 average rating, 144 reviews

Top guest favourite

Cottage in Southold

Adorable Cottage

2 bedrooms, 4 queen beds, 1 bathroom

13–18 Sept

$3,021 SGD for 5 nights

4.95 out of 5 average rating, 75 reviews

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$10,783 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Southold

Southold Escape With Large Pool on Wine Trail

3 bedrooms, 3 double beds, 2.5 bathrooms

19–24 Jul

$8,030 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

13–20 Jul

$22,025 SGD for 7 nights

Free cancellation

4.94 out of 5 average rating, 32 reviews

Guest favourite

Home in Southold

Shelter Bay Cove Waterfront Escape

3 bedrooms, 3 queen beds, 2 bathrooms

5–12 Sept

$6,821 SGD for 7 nights

4.97 out of 5 average rating, 30 reviews

Home in Southold

Luxury North Fork Beachfront Escape Near Greenport

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$9,942 SGD for 5 nights

4.93 out of 5 average rating, 15 reviews

Guest favourite

Home in Southold

Le Petit Cottage, Southold, NY

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

$2,195 SGD for 5 nights

4.91 out of 5 average rating, 79 reviews

Top guest favourite

Home in Southold

Charming Ranch in North Fork

3 bedrooms, 5 beds, 1 bathroom

18–23 Jul

$3,925 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Home in Southold

Country Beach Home!

4 bedrooms, 8 beds, 2.5 bathrooms

14–19 Aug

$7,409 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

3 bedrooms, 5 beds, 2.5 bathrooms

1–7 Jul

5.0 out of 5 average rating, 45 reviews