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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

27 Jul – 1 Aug

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4.89 out of 5 average rating, 197 reviews

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds, 3.5 bathrooms

11–18 Jul

$11,538 SGD for 7 nights

5.0 out of 5 average rating, 26 reviews

Home in Amagansett

Unit 211: Cottage | Ocean View | Striper

2 bedrooms, 1 bathroom

20–25 Sept

$4,145 SGD for 5 nights

Free cancellation

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds, 2 bathrooms

8–15 Sept

$4,116 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in East Hampton

East Hampton Rental w/ Pool, Moments to Amenities

4 bedrooms, 5 beds, 3 bathrooms

1–6 Aug

$9,242 SGD for 5 nights

5.0 out of 5 average rating, 82 reviews

Top guest favourite

Home in East Hampton

Elegant Springs Retreat (New Construction)

4 bedrooms, 3.5 bathrooms

13–18 Sept

$7,375 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in East Marion

POOL + Beach Oasis! Winter deals 2+ nights!

5 bedrooms, 5 beds, 3 bathrooms

4–9 Oct

$6,250 SGD for 5 nights

4.97 out of 5 average rating, 29 reviews

Top guest favourite

Home in East Hampton

Water view with Exceptional Light

3 bedrooms, 3 beds, 2 bathrooms

18–23 Oct

$5,277 SGD for 5 nights

4.96 out of 5 average rating, 67 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

11–16 Jul

$12,803 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds, 3 bathrooms

2–7 Aug

$9,526 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds, 2 bathrooms

28 Sept – 3 Oct

$4,014 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 63 reviews

Guest favourite

Home in East Lyme

The Big Bohemian Beach Bungalow 5 Br 3.5 Bath

5 bedrooms, 12 beds, 3.5 bathrooms

23–28 Aug

$6,935 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Home in East Hampton

Bay Access Cottage + Pilates Gym

2 bedrooms, 4 beds, 1 bathroom

20–25 Sept

$2,210 SGD for 5 nights

5.0 out of 5 average rating, 65 reviews

Top guest favourite

Home in Sag Harbor

Sag Harbor Chic Mid-Century Retreat

3 bedrooms, 4 beds, 2 bathrooms

9–14 Aug

$6,116 SGD for 5 nights

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Home in Clinton

The Connecticut Cottage | Historic Modern Charm

2 bedrooms, 2 beds, 2 bathrooms

14–19 Aug

$2,935 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

9–14 Aug

$10,091 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 38 reviews

Guest favourite

Home in Sag Harbor

Sag Harbor Summer House

3 bedrooms, 4 beds, 2 bathrooms

4–9 Sept

$9,649 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Home in East Hampton

East Hampton Retreat - Steps from Sammy’s Beach

5 bedrooms, 6 beds, 2.5 bathrooms

7–12 Sept

$10,670 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

23–28 Jul

$7,088 SGD for 5 nights

4.91 out of 5 average rating, 93 reviews