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 6

Guest favourite

Home in Southold

Le Petit Cottage, Southold, NY

2 bedrooms, 3 beds, 1 private bathroom

10–15 Oct

,

4.89 out of 5 average rating, 89 reviews

Photo 1 of 6

Home in East Hampton

East Hampton Beach House | Private Beach

4 bedrooms, 5 beds, 3 bathrooms

8–13 Sept

$4,766 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 6

Home in Greenport

Greenport Beachfront Home | Private Beach & Sunset

4 bedrooms, 7 beds, 2 bathrooms

6–11 Sept

$7,700 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Photo 1 of 6

Guest favourite

Home in East Hampton

Charming Home for a Perfect Escape

5 bedrooms, 7 beds, 3 bathrooms

27 Sept – 2 Oct

$6,892 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Photo 1 of 6

Top guest favourite

Home in Montauk

Oceanfront Home Downtown Montauk

3 bedrooms, 6 beds, 1.5 bathrooms

3–8 Nov

4.91 out of 5 average rating, 34 reviews

Photo 1 of 6

Home in Shelter Island

Waterfront Retreat | Spa Pool, Sauna & Dock

3 bedrooms, 3 beds, 3.5 bathrooms

13–18 Sept

$8,344 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 6

Top guest favourite

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

3 bedrooms, 5 beds, 2.5 bathrooms

18–23 Sept

$3,160 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 177 reviews

Photo 1 of 6

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

1–8 Sept

$18,964 SGD for 7 nights

Free cancellation

4.94 out of 5 average rating, 35 reviews

Photo 1 of 6

Top guest favourite

Home in East Hampton

Elegant Springs Retreat (New Construction)

4 bedrooms, 3.5 bathrooms

13–18 Sept

$9,194 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Photo 1 of 6

Top guest favourite

Home in Sag Harbor

Sag Harbor Summer House

3 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

5.0 out of 5 average rating, 15 reviews

Photo 1 of 6

Guest favourite

Home in Old Lyme

Make the "BlueBird" your new summer vacation home!

2 bedrooms, 2 beds, 2 bathrooms

28 Sept – 3 Oct

$1,564 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 5 reviews

Photo 1 of 6

Home in Cutchogue

Steps to Beach, Vineyards, Farm Stands & Village

3 bedrooms, 3 beds, 2 bathrooms

7–12 Sept

$5,084 SGD for 5 nights

New place to stay

Photo 1 of 6

Luxe

Villa in East Hampton

Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess

3 bedrooms, 3 beds, 3.5 bathrooms

13–18 Sept

$6,183 SGD for 5 nights

4.99 out of 5 average rating, 67 reviews

Photo 1 of 6

Superhost

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$5,190 SGD for 5 nights

4.97 out of 5 average rating, 129 reviews

Photo 1 of 6

Top guest favourite

Home in Greenport

Pennington House

3 bedrooms, 3 beds, 2.5 bathrooms

6–11 Sept

$5,909 SGD for 5 nights

5.0 out of 5 average rating, 33 reviews

Photo 1 of 6

Guest favourite

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

3 bedrooms, 4 beds, 2.5 bathrooms

13–18 Sept

4.91 out of 5 average rating, 201 reviews

Photo 1 of 6

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

7–14 Sept

Free cancellation

5.0 out of 5 average rating, 3 reviews

Photo 1 of 6

Top guest favourite

Home in East Marion

Bohemian Old Life Saving Station with Beach & Pool

6 bedrooms, 8 beds, 4 bathrooms

8–15 Sept

$16,108 SGD for 7 nights

4.97 out of 5 average rating, 114 reviews

Photo 1 of 6

Top guest favourite

Home in East Hampton

East Hampton Escape | Pool & Private Beach Access

4 bedrooms, 4 beds, 2 bathrooms

7–12 Sept

$5,656 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews