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Search results; Over 1,000 homes in Southold

Guest favourite

Cottage in Southold

Cozy Cottage on the Great Pond near beach.

2 bedrooms, 3 beds, 1.5 private bathrooms

11–16 Oct

$2,244 SGD for 5 nights

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4.89 out of 5 average rating, 197 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds, 2.5 bathrooms

24–29 Jul

$8,818 SGD for 5 nights

Free cancellation

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds, 3 bathrooms

3–8 Aug

$7,410 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in East Hampton

Private East Hampton Oasis

3 bedrooms, 3 beds, 3.5 bathrooms

21–27 Jul

$10,424 SGD for 6 nights

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

28 Jul – 2 Aug

$6,087 SGD for 5 nights

4.88 out of 5 average rating, 99 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

5–12 Aug

$9,587 SGD for 7 nights

Free cancellation

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,075 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 40 reviews

Home in Sag Harbor

Charming house in Sag Harbor.

3 bedrooms, 3 beds, 2 bathrooms

14–19 Sept

$4,642 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds, 3 bathrooms

22–27 Sept

$6,166 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Superhost

Cabin in East Hampton

Modern Cabin near the Beach

3 bedrooms, 6 beds, 3 bathrooms

10–15 Aug

$7,229 SGD for 5 nights

Guest favourite

Home in Shelter Island

Shelter Island House: Peaceful Retreat

3 bedrooms, 3 beds, 2 bathrooms

6–11 Aug

$8,028 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 28 reviews

Superhost

Flat in Mattituck

Vineyard Views: Private Patio and BBQ, Farm Access

1 bedroom, 2 queen beds, 1 bathroom

26–31 Jul

$2,895 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds, 1 bathroom

8–13 Aug

$1,910 SGD for 5 nights

5.0 out of 5 average rating, 28 reviews

Guest favourite

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds, 3 bathrooms

30 Aug – 4 Sept

$9,511 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds, 2 bathrooms

8–15 Sept

$4,004 SGD for 7 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Cottage in Southampton

Towd Point Beach Cottage w heated pool

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

4.98 out of 5 average rating, 48 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

21–26 Jul

$11,718 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in Clinton

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

4 bedrooms, 5 beds, 3 bathrooms

26–31 Jul

4.95 out of 5 average rating, 85 reviews

Top guest favourite

Home in Old Saybrook

Desirable Fenwood Beach-walk to beach-dogs allowed

3 bedrooms, 3 beds, 1.5 bathrooms

13–18 Sept

$2,968 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews