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

Guest house in Southold

Southold- Adorable 1 Bedroom Cottage

1 bedroom, 1 bed, 1 private bathroom

4–9 Oct

$1,814 SGD for 5 nights

,

4.91 out of 5 average rating, 86 reviews

Superhost

Home in Clinton

The Blue Mermaid

3 bedrooms, 3 beds

3–8 Aug

$7,119 SGD for 5 nights

Free cancellation

Top guest favourite

Home in Branford

Adorable Beach House on LI Sound

1 bedroom, 2 beds

27 Sept – 2 Oct

$1,566 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 104 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds

7–12 Aug

$12,547 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Superhost

Tent in East Hampton

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

1 bedroom, 1 queen bed

23–28 Aug

$1,512 SGD for 5 nights

4.86 out of 5 average rating, 56 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds

9–14 Aug

$5,934 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Superhost

Home in Montauk

Sea Ranch At Ditch Plains - Welcome To The Beach

4 bedrooms, 5 beds

31 Aug – 6 Sept

Extended stay discount

Home in East Hampton

Eauclaire Street cozy cottage

3 bedrooms, 3 beds

2–7 Aug

$6,348 SGD for 5 nights

Free cancellation

New place to stay

Top guest favourite

Guest suite in East Hampton

Hamptons Dream Suite

1 bedroom, 3 beds

2–7 Aug

Free cancellation

4.98 out of 5 average rating, 160 reviews

Top guest favourite

Home in East Hampton

Hamptons Beach House

4 bedrooms, 5 beds

22–27 Sept

$5,558 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Home in Greenport

The North Star: Greenport Waterview Beach Getaway

3 bedrooms, 4 beds

28 Sept – 3 Oct

$3,981 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 65 reviews

Top guest favourite

Home in Old Saybrook

The Saybrook Point Bungalow, Stroll to Downtown

2 bedrooms, 3 beds

7–12 Sept

$1,951 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 22 reviews

Top guest favourite

Cottage in Sag Harbor

Charming Cottage in Historic Sag Harbor

1 bedroom, 1 king bed

20–25 Sept

$2,464 SGD for 5 nights

5.0 out of 5 average rating, 69 reviews

Home in East Hampton

5 bedroom waterfront on Gardiner's Bay

5 bedrooms, 10 beds

29 Aug – 3 Sept

$9,599 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Superhost

Villa in Southampton

US Golf Open & Ocean View Retreat, Walk to Event

4 bedrooms, 4 beds

15–20 Oct

$2,371 SGD for 5 nights

Free cancellation

4.83 out of 5 average rating, 6 reviews

Top guest favourite

Rooms in Greenport

Chestnut View Room own private bathroom

2 bedrooms, 3 queen beds

6–11 Sept

$2,136 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 95 reviews

Top guest favourite

Holiday home in Hampton Bays

Hamptons house -ultra-private backyard, near beach

3 bedrooms, 4 beds

20–25 Sept

$3,477 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds

6–11 Sept

$9,952 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 41 reviews

Guest favourite

Home in Old Saybrook

Summertime in Old Saybrook on the Oyster River

5 bedrooms, 6 beds

9–14 Nov

$5,829 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews