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

Search results; Over 1,000 homes in Southold

Guest favourite

Cottage in Southold

Bordeaux meets Côte d’Azur—1763 Historic Farmhouse

3 bedrooms, 4 beds, 2 private bathrooms

15–22 Aug

,

4.92 out of 5 average rating, 66 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds

24–29 Jul

$8,827 SGD for 5 nights

Pay $0 today

Free cancellation

Home in Laurel

North Fork Luxury Retreat with Exceptional Comfort

5 bedrooms, 5 beds

3–8 Aug

$7,418 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

6–11 Sept

$10,085 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 40 reviews

Home in Southold

Sunset Cottage

3 bedrooms, 4 beds

22–29 Jul

$7,322 SGD for 7 nights

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Shelter Island

Shelter Island House: Peaceful Retreat

3 bedrooms, 3 beds

6–11 Aug

$8,035 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 28 reviews

Top guest favourite

Home in Branford

Adorable Beach House on LI Sound

1 bedroom, 2 beds

27 Sept – 2 Oct

$1,587 SGD for 5 nights

Pay $0 today

Free cancellation

4.98 out of 5 average rating, 100 reviews

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed

26–31 Jul

4.86 out of 5 average rating, 56 reviews

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds

30 Aug – 4 Sept

$6,602 SGD for 5 nights

4.94 out of 5 average rating, 54 reviews

Guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds

8–13 Aug

$1,912 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 28 reviews

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds

8–15 Sept

$4,008 SGD for 7 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 12 reviews

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 8 beds

30 Aug – 4 Sept

$9,521 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds

8–15 Aug

$4,227 SGD for 7 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 74 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds

28 Sept – 3 Oct

$4,012 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 65 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds

22–27 Sept

$6,172 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Guest house in Madison

Charming Cottage is 1 Mile from Town and Beach

1 bedroom, 1 double bed

13–18 Sept

$1,333 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Home in Sag Harbor

Charming house in Sag Harbor.

3 bedrooms, 3 beds

14–19 Sept

$4,646 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

20–25 Jul

$11,729 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Greenport

Aqua Vista

2 bedrooms, 3 beds

23–28 Aug

$2,400 SGD for 5 nights

4.95 out of 5 average rating, 263 reviews