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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

$2,246 SGD for 5 nights

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4.89 out of 5 average rating, 197 reviews

Home in East Hampton

East Hamptons 3BR Private +Den Private Entrance

3 bedrooms, 2 queen beds, 2 bathrooms

1–6 Aug

$7,917 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Flat in Greenport

Greenport Harbor Apartment

3 bedrooms, 4 beds, 2 bathrooms

2–7 Aug

Free cancellation

4.96 out of 5 average rating, 97 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

1–6 Aug

$12,946 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

3–8 Aug

$5,978 SGD for 5 nights

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Home in East Hampton

Private East Hampton Oasis

3 bedrooms, 3 beds, 3.5 bathrooms

25–31 Aug

Book early to save

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds, 3 bathrooms

22–27 Sept

$6,171 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

1–8 Aug

$4,227 SGD for 7 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 74 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

6–11 Dec

$3,529 SGD for 5 nights

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed, 1 bathroom

1–6 Aug

$1,672 SGD for 5 nights

Free cancellation

4.86 out of 5 average rating, 56 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds, 2 bathrooms

29 Aug – 3 Sept

$9,671 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Superhost

Cabin in East Hampton

Modern Cabin near the Beach

3 bedrooms, 6 beds, 3 bathrooms

10–15 Aug

$7,235 SGD for 5 nights

Free cancellation

Guest favourite

Home in Madison

Fabulous pool in beach town!

4 bedrooms, 4 beds, 2.5 bathrooms

21–26 Aug

$5,782 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 22 reviews

Home in East Hampton

Tranquil Springs Cottage

2 bedrooms, 2 queen beds, 1 bathroom

23–28 Aug

$4,135 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Flat in Greenport

Greenport Condo with Stunning Views & Beach Access

2 bedrooms, 4 beds, 2 bathrooms

30 Aug – 4 Sept

$4,338 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds, 2 bathrooms

28 Sept – 3 Oct

$4,011 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 65 reviews

Top guest favourite

Boat in Old Lyme

Sunny Daze

1 bedroom, 1 queen bed, 1 bathroom

1–6 Aug

$2,079 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 103 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds, 2.5 bathrooms

1–6 Aug

Pay $0 today

Free cancellation

Top guest favourite

Home in East Lyme

Charming Cottage in Private Oak Grove Beach

3 bedrooms, 6 beds, 1 bathroom

8–13 Nov

$1,312 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 72 reviews