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Search results; Over 1,000 homes in Southold

Guest favourite

Guest house in Southold

Southold- Adorable 1 Bedroom Cottage

1 bedroom, 1 bed, 1 private bathroom

23–28 Aug

$1,713 SGD for 5 nights

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4.9 out of 5 average rating, 83 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds

24–29 Jul

Pay $0 today

Free cancellation

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

19–24 Jul

$11,723 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Shelter Island House: Peaceful Retreat

3 bedrooms, 3 beds

6–11 Aug

$8,031 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 28 reviews

Home in Southold

Sunset Cottage

3 bedrooms, 4 beds

20–27 Jul

$7,318 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds

3–8 Aug

$7,414 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Home in Old Saybrook

Red Bird Waterfront Home. Dock available extra!

3 bedrooms, 3 beds

26–31 Jul

$7,381 SGD for 5 nights

4.94 out of 5 average rating, 35 reviews

Superhost

Flat in Mattituck

Vineyard Views: Private Patio and BBQ, Farm Access

1 bedroom, 2 queen beds

19–24 Jul

$2,949 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds

19–26 Jul

$7,007 SGD for 7 nights

Pay $0 today

Free cancellation

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds

9–14 Aug

$6,598 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 54 reviews

Home in Amagansett

Unit 211: Cottage | Ocean View | Striper

2 bedrooms

20–25 Sept

$4,140 SGD for 5 nights

Pay $0 today

Free cancellation

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds

29 Aug – 3 Sept

$9,667 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds

8–13 Aug

$1,911 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 28 reviews

Home in Sag Harbor

Charming house in Sag Harbor.

3 bedrooms, 3 beds

14–19 Sept

$4,644 SGD for 5 nights

Pay $0 today

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

22–27 Sept

$6,169 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds

30 Aug – 4 Sept

$9,515 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Southampton

Towd Point Beach Cottage w heated pool

3 bedrooms, 4 beds

2–7 Aug

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Home in Sag Harbor

Sag Harbor Chic Mid-Century Retreat

3 bedrooms, 4 beds

20–25 Sept

$4,979 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 77 reviews

Top guest favourite

Home in Old Saybrook

Best of both worlds!

3 bedrooms, 4 beds

24–29 Aug

$2,135 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 111 reviews