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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

$1,714 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, 2.5 bathrooms

24–29 Jul

$8,827 SGD for 5 nights

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Free cancellation

Home in Southold

Sunset Cottage

3 bedrooms, 4 beds, 2.5 bathrooms

22–29 Jul

$7,322 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

20–27 Jul

$7,011 SGD for 7 nights

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Free cancellation

Superhost

Tent in East Hampton

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

1 bedroom, 1 queen bed, 1 bathroom

26–31 Jul

Free cancellation

4.86 out of 5 average rating, 56 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,085 SGD for 5 nights

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Free cancellation

4.95 out of 5 average rating, 40 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

$6,093 SGD for 5 nights

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Free cancellation

4.88 out of 5 average rating, 99 reviews

Top guest favourite

Home in Branford

Adorable Beach House on LI Sound

1 bedroom, 2 beds, 1.5 bathrooms

27 Sept – 2 Oct

$1,587 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 100 reviews

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds, 2 bathrooms

8–15 Sept

$4,008 SGD for 7 nights

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Free cancellation

5.0 out of 5 average rating, 12 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds, 3 bathrooms

30 Aug – 4 Sept

$9,521 SGD for 5 nights

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5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds, 1 bathroom

8–13 Aug

$1,912 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 28 reviews

Guest favourite

Home in Shelter Island

Shelter Island House: Peaceful Retreat

3 bedrooms, 3 beds, 2 bathrooms

6–11 Aug

$8,035 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

8–15 Aug

$4,227 SGD for 7 nights

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Free cancellation

4.99 out of 5 average rating, 74 reviews

Guest favourite

Cottage in Old Lyme

The Solo Shore Cottage | Walk to Beach + Sun Porch

2 bedrooms, 4 beds, 1 bathroom

18–23 Aug

$3,522 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Old Saybrook

Best of both worlds!

3 bedrooms, 4 beds, 2 bathrooms

24–29 Aug

$2,107 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 111 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds, 2 bathrooms

29 Aug – 3 Sept

$9,673 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Home in Sag Harbor

Charming house in Sag Harbor.

3 bedrooms, 3 beds, 2 bathrooms

14–19 Sept

$4,646 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 10 reviews

Home in Sag Harbor

1 Acre Sag Harbor Gem

4 bedrooms, 5 beds, 3 bathrooms

23–30 Aug

$15,374 SGD for 7 nights

Guest favourite

Home in Greenport

Aqua Vista

2 bedrooms, 3 beds, 1 bathroom

23–28 Aug

$2,400 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 263 reviews