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Search results; Over 1,000 homes in Southold

Descriptions are based on details hosts provide

Home in Southold

The Shorecrest Beach House

4 bedrooms, 6 beds, 2 private bathrooms

14–19 Oct

$5,784 SGD for 5 nights

,

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Shelter Island

New build with pool and beach access

3 bedrooms, 5 beds, 3 bathrooms

15–20 Jul

$12,173 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Superhost

Home in Old Saybrook

Beachfront Home with Amazing Views | 5BR Sleeps 11

5 bedrooms, 7 beds, 2 bathrooms

15–20 Aug

$9,836 SGD for 5 nights

New place to stay

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds, 2.5 bathrooms

24–29 Jul

Free cancellation

Top guest favourite

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds, No bathroom

9–14 Aug

$2,298 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 92 reviews

Home in Shelter Island Heights

Century-old shingle house on the creek

4 bedrooms, 5 beds, 3.5 bathrooms

15–22 Jul

$7,004 SGD for 7 nights

Free cancellation

Guest favourite

Flat in Mattituck

Open-concept layout, deck, and nearby vineyards

2 bedrooms, 2 queen beds, 1 bathroom

19–24 Jul

$3,308 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds, 3 bathrooms

3–8 Aug

$7,410 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in Greenport

Bayview house with salt water pool & private chef

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,820 SGD for 5 nights

4.9 out of 5 average rating, 10 reviews

Top guest favourite

Cottage in Old Lyme

Fire pit, outdoor shower, walk to beach

2 bedrooms, 4 beds, 1 bathroom

2–7 Aug

$3,389 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in East Marion

Private beach on Peconic Bay

3 bedrooms, 4 beds, 1.5 bathrooms

1–8 Aug

Weekly discount

4.88 out of 5 average rating, 42 reviews

Home in East Hampton

Tranquil Springs Cottage

2 bedrooms, 2 queen beds, 1 bathroom

23–28 Aug

$4,131 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Southampton

10 mins from US OPEN Cottage w heated pool

3 bedrooms, 4 beds, 2 bathrooms

16–21 Jul

$14,426 SGD for 5 nights

4.98 out of 5 average rating, 48 reviews

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds, 3.5 bathrooms

16–23 Jul

$11,519 SGD for 7 nights

5.0 out of 5 average rating, 26 reviews

Home in East Hampton

Architect-designed beach house on Gardiner’s Bay

5 bedrooms, 10 beds, 2 bathrooms

29 Aug – 3 Sept

$9,663 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Home in Westhampton Beach

Westhampton Beach Oasis

7 bedrooms, 8 beds, 5 bathrooms

26–31 Jul

$21,182 SGD for 5 nights

New place to stay

Top guest favourite

Home in Southold

Exclusive beach access and sunset views

4 bedrooms, 4 beds, 2 bathrooms

21–26 Jul

$11,451 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Home in Sag Harbor

Sun-Filled, Custom-Designed 5-bedroom Sag Harbor

5 bedrooms, 7 beds, 3 bathrooms

20–25 Jul

$30,380 SGD for 5 nights

New place to stay

Home in East Hampton

Finished basement, fire pit, and private backyard

5 bedrooms, 8 beds, 3 bathrooms

30 Aug – 4 Sept

$9,511 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews