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Search results; Over 1,000 homes in Southold

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds, 2.5 bathrooms

24–29 Jul

$8,917 SGD for 5 nights

Home in Southold

Sunset Cottage

3 bedrooms, 4 beds, 2.5 bathrooms

21–28 Jul

$7,322 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds, 3 bathrooms

3–8 Aug

$7,418 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

20–25 Jul

$11,729 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed, 1 bathroom

26–31 Jul

$1,524 SGD for 5 nights

4.86 out of 5 average rating, 56 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

20–27 Jul

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

9–14 Aug

$10,085 SGD for 5 nights

4.95 out of 5 average rating, 40 reviews

Guest favourite

Home in Old Saybrook

Red Bird Waterfront Home. Dock available extra!

3 bedrooms, 3 beds, 2 bathrooms

26–31 Jul

$7,385 SGD for 5 nights

4.94 out of 5 average rating, 35 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,602 SGD for 5 nights

4.94 out of 5 average rating, 54 reviews

Superhost

Flat in Mattituck

Vineyard Views: Private Patio and BBQ, Farm Access

1 bedroom, 2 queen beds, 1 bathroom

20–25 Jul

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

$1,912 SGD for 5 nights

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

5.0 out of 5 average rating, 28 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

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

$4,008 SGD for 7 nights

5.0 out of 5 average rating, 12 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

4.99 out of 5 average rating, 74 reviews

Guest favourite

Guest house in Madison

Charming Cottage is 1 Mile from Town and Beach

1 bedroom, 1 double bed, 1 bathroom

13–18 Sept

$1,333 SGD for 5 nights

5.0 out of 5 average rating, 5 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

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

$6,172 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews