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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

5–10 Sept

$5,584 SGD for 5 nights

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4.97 out of 5 average rating, 31 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 6 Sept

Extended stay discount

Guest favourite

Rooms in East Hampton

Two Lovely Private Rooms

2 bedrooms, 2 queen beds, 1 bathroom

7–12 Sept

$3,783 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

9–14 Aug

$5,939 SGD for 5 nights

4.92 out of 5 average rating, 13 reviews

Home in East Marion

The Gathering House | North Fork Retreat

4 bedrooms, 5 beds, 3.5 bathrooms

31 Aug – 5 Sept

$9,577 SGD for 5 nights

New place to stay

Guest favourite

Home in Mattituck

Lakehouse Getaway North Fork

3 bedrooms, 5 beds, 2 bathrooms

16–21 Aug

$7,868 SGD for 5 nights

5.0 out of 5 average rating, 46 reviews

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

30 Aug – 6 Sept

$20,274 SGD for 7 nights

4.94 out of 5 average rating, 34 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds, 2 bathrooms

29 Aug – 3 Sept

$9,608 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in East Hampton

Elegant Springs Retreat (New Construction)

4 bedrooms, 3.5 bathrooms

13–18 Sept

$8,383 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Greenport

Aqua Vista

2 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

$2,799 SGD for 5 nights

4.95 out of 5 average rating, 265 reviews

Top guest favourite

Home in Montauk

Dockside 2BR - Marina - Dining - Charter Access Un

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

$2,776 SGD for 5 nights

4.97 out of 5 average rating, 31 reviews

Home in Amagansett

Lazy Point Gem w access to Private Beach

3 bedrooms, 3 beds, 1 bathroom

17–22 Aug

$5,256 SGD for 5 nights

New place to stay

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

7–12 Aug

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in East Marion

North Fork Coastal living in East Marion

4 bedrooms, 4 beds, 2.5 bathrooms

18–23 Aug

4.88 out of 5 average rating, 99 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,558 SGD for 5 nights

4.95 out of 5 average rating, 55 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

7–14 Aug

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Old Saybrook

Desirable Fenwood Beach-walk to beach-dogs allowed

3 bedrooms, 3 beds, 1.5 bathrooms

22–27 Sept

$3,064 SGD for 5 nights

5.0 out of 5 average rating, 15 reviews

Guest favourite

Home in Old Saybrook

Summertime in Old Saybrook on the Oyster River

5 bedrooms, 6 beds, 2.5 bathrooms

13–18 Sept

$6,572 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Home in Southold

The Shorecrest Beach House

4 bedrooms, 6 beds, 2 bathrooms

19–24 Oct

$5,327 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews