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

Flat in Southold

Bright, Southold Studio Apt near beach & town

Studio, 2 beds, 1 private bathroom

16–21 Aug

$2,029 SGD for 5 nights

,

4.95 out of 5 average rating, 154 reviews

Superhost

Home in Sag Harbor

Sag Harbor New Construction

7 bedrooms, 9 beds, 8 bathrooms

16–21 Aug

$33,225 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Flat in Mattituck

Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines

2 bedrooms, 2 queen beds, 1 bathroom

16–21 Aug

5.0 out of 5 average rating, 8 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 6 Sept

Extended stay discount

Top guest favourite

Home in Southold

Luxury by the Sea!!

3 bedrooms, 4 beds, 2.5 bathrooms

30 Aug – 4 Sept

$6,541 SGD for 5 nights

4.95 out of 5 average rating, 55 reviews

Guest favourite

Home in Mattituck

Lakehouse Getaway North Fork

3 bedrooms, 5 beds, 2 bathrooms

16–21 Aug

5.0 out of 5 average rating, 47 reviews

Guest favourite

Cottage in Old Lyme

The Solo Shore Cottage | Walk to Beach + Sun Porch

2 bedrooms, 4 beds, 1 bathroom

23–28 Aug

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

30 Aug – 6 Sept

$20,224 SGD for 7 nights

Free cancellation

4.94 out of 5 average rating, 34 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

30 Aug – 4 Sept

$12,602 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

30 Aug – 4 Sept

$5,924 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Guest favourite

Home in Sag Harbor

9 Acre Luxury Compound in Sag Harbor NY

7 bedrooms, 10 beds, 8.5 bathrooms

11–16 Oct

$11,999 SGD for 5 nights

4.99 out of 5 average rating, 146 reviews

Guest favourite

Home in East Marion

Charming North Fork escape by the beach

3 bedrooms, 4 beds, 2 bathrooms

8–15 Sept

$3,886 SGD for 7 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Old Lyme

Casa Swan

3 bedrooms, 4 beds, 1 bathroom

24–29 Aug

$1,772 SGD for 5 nights

5.0 out of 5 average rating, 32 reviews

Guest house in Hampton Bays

Tiana Hideaway - Private Hamptons Studio Retreat

1 bathroom

30 Aug – 4 Sept

$2,139 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Home in Wainscott

Charming Wainscott Cottage

2 bedrooms, 3 beds, 1.5 bathrooms

31 Aug – 5 Sept

$4,251 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in Old Lyme

Cozy Beach Cottage with short walk to the beach

4 bedrooms, 5 beds, 1.5 bathrooms

23–28 Aug

$4,075 SGD for 5 nights

4.97 out of 5 average rating, 198 reviews

Home in East Hampton

The Springs House

4 bedrooms, 5 beds, 2.5 bathrooms

8–13 Sept

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Home in East Hampton

Elegant Springs Retreat (New Construction)

4 bedrooms, 3.5 bathrooms

13–18 Sept

$8,326 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Guest suite in East Hampton

Hamptons Dream Suite

1 bedroom, 3 beds, 1 bathroom

23–28 Aug

$2,800 SGD for 5 nights

4.98 out of 5 average rating, 161 reviews