We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Southold

Photo 1 of 29

Cottage in Southold

Cozy & Chic Beach Cottage!

2 bedrooms, 3 beds, 0.5 private bathroom

18–23 Oct

$2,088 SGD for 5 nights

,

4.74 out of 5 average rating, 203 reviews

Photo 1 of 29

Home in Shelter Island

NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

5 bedrooms, 8 beds, 4.5 bathrooms

30 Sept – 7 Oct

Photo 1 of 23

Home in East Hampton

East Hampton Beach House | Private Beach

4 bedrooms, 5 beds, 3 bathrooms

20–25 Sept

$4,466 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Photo 1 of 29

Top guest favourite

Home in Greenport

Greenport Beachfront Home | Private Beach & Sunset

4 bedrooms, 7 beds, 2 bathrooms

19–24 Sept

5.0 out of 5 average rating, 8 reviews

Photo 1 of 29

Top guest favourite

Home in East Hampton

Beautiful east hampton cottage by the bay

4 bedrooms, 2 queen beds, 2.5 bathrooms

5–10 Oct

Free cancellation

5.0 out of 5 average rating, 16 reviews

Photo 1 of 29

Home in Cutchogue

Steps to Beach, Vineyards, Farm Stands & Village

3 bedrooms, 3 beds, 2 bathrooms

20–25 Sept

$5,104 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Photo 1 of 23

Guest favourite

Home in Orient

Luxury Escape - Saltwater Pool

4 bedrooms, 7 beds, 2.5 bathrooms

20–25 Sept

$5,314 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Photo 1 of 29

Guest favourite

Home in Orient

Orient Point Family Waterfront Home

5 bedrooms, 9 beds, 3.5 bathrooms

3–8 Oct

$9,512 SGD for 5 nights

4.96 out of 5 average rating, 27 reviews

Photo 1 of 6

Top guest favourite

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds, No bathroom

10–15 Nov

$2,170 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 104 reviews

Photo 1 of 29

Guest favourite

Home in Sag Harbor

9 Acre Luxury Compound in Sag Harbor NY

7 bedrooms, 10 beds, 8.5 bathrooms

11–16 Oct

$11,643 SGD for 5 nights

4.99 out of 5 average rating, 148 reviews

Photo 1 of 29

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

20–25 Sept

$6,266 SGD for 5 nights

4.95 out of 5 average rating, 44 reviews

Photo 1 of 29

Top guest favourite

Home in Amagansett

Bliss by the Ocean!

6 bedrooms, 7 beds, 5.5 bathrooms

12–17 Oct

4.94 out of 5 average rating, 71 reviews

Photo 1 of 29

Guest favourite

Home in Southampton

Vogue Editors Home, Featured Hamptons Mag, Elle D.

4 bedrooms, 4 beds, 7.5 bathrooms

11–16 Oct

5.0 out of 5 average rating, 6 reviews

Photo 1 of 27

Top guest favourite

Home in Shelter Island

Light, spacious 3bdr home steps to Wades Beach

3 bedrooms, 4 beds, 2.5 bathrooms

22–27 Sept

4.93 out of 5 average rating, 45 reviews

Photo 1 of 29

Luxe

Home in Montauk

Montauk modern 7-bedroom Heated Pool & hot tub

7 bedrooms, 10 beds, 5 bathrooms

25–30 Oct

Free cancellation

5.0 out of 5 average rating, 40 reviews

Photo 1 of 15

Superhost

Home in Old Lyme

Surf Cottage (1 Minute Walk to Private Beach)

2 bedrooms, 3 beds, 1 bathroom

26 Sept – 1 Oct

$1,647 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 10

Top guest favourite

Home in Sag Harbor

Sag Harbor home away from home

2 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$3,481 SGD for 5 nights

4.98 out of 5 average rating, 237 reviews

Photo 1 of 29

Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

21–26 Sept

New place to stay

Photo 1 of 29

Top guest favourite

Home in East Marion

Long Island home with pool 1 mile from Greenport

3 bedrooms, 3 beds, 2 bathrooms

13–18 Oct

5.0 out of 5 average rating, 24 reviews