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Search results; Over 1,000 homes in Southold

Guest favourite

Flat in Southold

Bright, Southold Studio Apt near beach & town

Studio, 2 beds, 1 private bathroom

12–17 Jul

$2,101 SGD for 5 nights

,

4.94 out of 5 average rating, 144 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Aug

$5,975 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 12 reviews

Superhost

Home in Sag Harbor

Sag Harbor retreat with pool

3 bedrooms, 4 beds, 1.5 bathrooms

6–11 Jul

$7,619 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

5–10 Jul

$12,939 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Home in Southold

Waterfront North Fork Retreat • Sunset & Vineyards

4 bedrooms, 5 beds, 3 bathrooms

19–26 Jul

$9,129 SGD for 7 nights

Guest favourite

Home in Southold

Le Petit Cottage, Southold, NY

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

$2,185 SGD for 5 nights

4.91 out of 5 average rating, 81 reviews

Top guest favourite

Place to stay in Cutchogue

Sunset Suite - walk to vineyards, beaches, & more

1 bedroom, 1 king bed, 1 bathroom

4–9 Oct

$1,317 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 177 reviews

Top guest favourite

Cottage in Southampton

10 mins from US OPEN Cottage w heated pool

3 bedrooms, 4 beds, 2 bathrooms

5–10 Jul

$13,061 SGD for 5 nights

4.98 out of 5 average rating, 47 reviews

Top guest favourite

Home in Southold

Greenport walk to beach & vineyard! Brand new home

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Jul

5.0 out of 5 average rating, 76 reviews

Guest favourite

Home in Southold

Family and Dog Friendly Private Beach

3 bedrooms, 3 queen beds, 2 bathrooms

25–30 Jul

$5,016 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Loft in Greenport

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

2 bedrooms, 3 beds, 2 bathrooms

5–10 Jul

4.97 out of 5 average rating, 35 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds, 2 bathrooms

4–9 Aug

$4,403 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 63 reviews

Top guest favourite

Home in East Marion

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

3 bedrooms, 3 beds, 3.5 bathrooms

10–17 Jul

$11,523 SGD for 7 nights

5.0 out of 5 average rating, 25 reviews

Top guest favourite

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

3 bedrooms, 5 beds, 2.5 bathrooms

6–12 Jul

$5,984 SGD for 6 nights

5.0 out of 5 average rating, 45 reviews

Guest favourite

Home in Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

2 bedrooms, 3 beds, 1 bathroom

7–12 Sept

$2,124 SGD for 5 nights

4.92 out of 5 average rating, 506 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

12–17 Sept

$3,083 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 73 reviews

Top guest favourite

Flat in Sag Harbor

Sag Harbor / Noyack Pad - private STUDIO apartment

2 beds, 1 bathroom

8–13 Jul

$2,086 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 181 reviews

Top guest favourite

Room in Southampton

Private suite at Pine Springs, Southampton, NY

2 beds, 1 bathroom

23–28 Jul

$2,855 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 18 reviews

Guest favourite

Home in Southold

Cottage by the beach

2 bedrooms, 2 beds, 1.5 bathrooms

9–14 Aug

$3,958 SGD for 5 nights

4.89 out of 5 average rating, 18 reviews