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Search results; Over 1,000 homes in Southold

Guest favourite

Home in Southold

Shelter Bay Cove Waterfront Escape

3 bedrooms, 3 beds, 2 private bathrooms

5–12 Sept

$6,806 SGD for 7 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

13–20 Jul

$6,255 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

$6,385 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 53 reviews

Top guest favourite

Home in Southold

Charming Ranch in North Fork

3 bedrooms, 5 beds, 1 bathroom

18–23 Jul

$3,916 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Home in Southold

Dockside Getaway in Southold NY

3 bedrooms, 5 beds, 3 bathrooms

2–7 Jul

$10,218 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 40 reviews

Flat in Southold

1BR Apartment - Beach Access - Wineries, Vineyards

1 bedroom, 1 queen bed, 1 bathroom

5–10 Jul

$2,541 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in Southold

Southold waterfront 4 bed, pool open til October

4 bedrooms, 5 beds, 3 bathrooms

24–29 Jul

$11,827 SGD for 5 nights

4.9 out of 5 average rating, 77 reviews

Home in Southold

Family and Dog Friendly Private Beach

3 bedrooms, 3 queen beds, 2 bathrooms

25 Jul – 1 Aug

$7,360 SGD for 7 nights

Free cancellation

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

Free cancellation

5.0 out of 5 average rating, 45 reviews

Home in Southold

Luxury North Fork Beachfront Escape Near Greenport

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$9,919 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 15 reviews

Guest favourite

Cottage in Southold

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

3 bedrooms, 4 beds, 2 bathrooms

8–15 Jul

Free cancellation

4.92 out of 5 average rating, 64 reviews

Top guest favourite

Home in Southold

Country Beach Home!

4 bedrooms, 8 beds, 2.5 bathrooms

30 Aug – 4 Sept

$7,163 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 16 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

$2,640 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 195 reviews

Guest favourite

Home in Southold

Southold Sea'renity

3 bedrooms, 5 beds, 2 bathrooms

30 Jul – 4 Aug

$5,769 SGD for 5 nights

Free cancellation

4.82 out of 5 average rating, 45 reviews

Top guest favourite

Home in Southold

Beach Front House

4 bedrooms, 4 beds, 2 bathrooms

19–24 Jul

$10,758 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

1–8 Jul

$10,403 SGD for 7 nights

Free cancellation

Guest favourite

Guest house in Southold

Southold- Adorable 1 Bedroom Cottage

1 bedroom, 1 queen bed, 1 bathroom

23–28 Aug

$1,717 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 80 reviews

Guest favourite

Home in Southold

Le Petit Cottage, Southold, NY

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

$2,190 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 79 reviews

Guest favourite

Home in Southold

Peconic Pearl Cottage

4 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$4,807 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews