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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

12–17 Oct

$1,812 SGD for 5 nights

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4.91 out of 5 average rating, 87 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

7–12 Aug

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

28 Sept – 3 Oct

$4,872 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Rooms in East Hampton

Two Lovely Private Rooms

2 bedrooms, 2 queen beds, 1 bathroom

7–12 Sept

$3,775 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 22 reviews

Home in East Marion

The Gathering House | North Fork Retreat

4 bedrooms, 5 beds, 3.5 bathrooms

31 Aug – 5 Sept

$9,556 SGD for 5 nights

New place to stay

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 6 Sept

Extended stay discount

Home in Amagansett

Lazy Point Gem w access to Private Beach

3 bedrooms, 3 beds, 1 bathroom

6–11 Aug

$5,501 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Superhost

Home in Sag Harbor

Sag Harbor New Construction

7 bedrooms, 9 beds, 8 bathrooms

10–15 Aug

$33,557 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Home in Old Saybrook

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace

3 bedrooms, 6 beds, 1.5 bathrooms

26–31 Aug

5.0 out of 5 average rating, 100 reviews

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed, 1 bathroom

6–11 Sept

$1,658 SGD for 5 nights

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

$9,587 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Mattituck

Lakehouse Getaway North Fork

3 bedrooms, 5 beds, 2 bathrooms

16–21 Aug

$7,851 SGD for 5 nights

5.0 out of 5 average rating, 46 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,544 SGD for 5 nights

4.95 out of 5 average rating, 55 reviews

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

30 Aug – 6 Sept

$20,231 SGD for 7 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 34 reviews

Top guest favourite

Home in East Hampton

Elegant Springs Retreat (New Construction)

4 bedrooms, 3.5 bathrooms

13–18 Sept

$8,372 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in East Marion

North Fork Coastal living in East Marion

4 bedrooms, 4 beds, 2.5 bathrooms

18–23 Aug

Pay $0 today

Free cancellation

4.88 out of 5 average rating, 99 reviews

Guest favourite

Home in Old Saybrook

Summertime in Old Saybrook on the Oyster River

5 bedrooms, 6 beds, 2.5 bathrooms

13–18 Sept

$6,558 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in Montauk

Dockside 2BR - Marina - Dining - Charter Access Un

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

$2,774 SGD for 5 nights

4.97 out of 5 average rating, 31 reviews

Guest favourite

Home in Greenport

Aqua Vista

2 bedrooms, 3 beds, 1 bathroom

28 Aug – 2 Sept

$3,548 SGD for 5 nights

4.95 out of 5 average rating, 265 reviews