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Search results; Over 1,000 homes in Southold

Top guest favourite

Home in East Marion

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

3 bedrooms, 3 beds

10–15 Aug

5.0 out of 5 average rating, 27 reviews

Guest favourite

Flat in Greenport

Greenport Harbor Apartment

3 bedrooms, 4 beds

2–7 Aug

4.96 out of 5 average rating, 97 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds

9–14 Aug

$5,974 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Home in East Hampton

The Springs House

4 bedrooms, 5 beds

11–18 Aug

$7,567 SGD for 7 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds

22–27 Sept

$6,167 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds

29 Aug – 3 Sept

$9,665 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Flat in Greenport

Greenport Condo with Stunning Views & Beach Access

2 bedrooms, 4 beds

30 Aug – 4 Sept

$4,335 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Home in Madison

Fabulous pool in beach town!

4 bedrooms, 4 beds

21–26 Aug

$5,778 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

Home in Southold

The Shorecrest Beach House

4 bedrooms, 6 beds

14–19 Oct

$5,785 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed

1–6 Aug

$1,671 SGD for 5 nights

4.86 out of 5 average rating, 56 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

1–6 Aug

$12,937 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds

1–6 Aug

Free cancellation

Home in East Hampton

Eauclaire Street cozy cottage

3 bedrooms, 3 beds

2–7 Aug

$6,391 SGD for 5 nights

Free cancellation

New place to stay

Home in East Hampton

Tranquil Springs Cottage

2 bedrooms, 2 queen beds

23–28 Aug

$4,132 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Home in Amagansett

Unit 211: Cottage | Ocean View | Striper

2 bedrooms

2–7 Oct

$4,291 SGD for 5 nights

Free cancellation

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds

30 Aug – 6 Sept

$20,394 SGD for 7 nights

Free cancellation

4.94 out of 5 average rating, 34 reviews

Guest favourite

Home in Sag Harbor

Hamptons Retreat | Pool, Hot Tub, Built-in BBQ

4 bedrooms, 5 beds

17–24 Aug

Weekly discount

Free cancellation

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds

28 Sept – 3 Oct

$4,008 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 65 reviews