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

Top guest favourite

Guest suite in Southold

Comfortable Suite, a walk to the beach

1 bedroom, 1 bed, 1 private bathroom

3–8 Oct

£893 total

,

4.94 out of 5 average rating, 159 reviews

Photo 1 of 15

Featured hotel

Hotel in Greenport

Oyster Estate, Classic king

1 bedroom, 1 king bed, 1 bathroom

4–9 Oct

£1,895 total

+£228 Airbnb credit

New place to stay

Photo 1 of 26

Featured hotel

Hotel in Bridgehampton

A Room at the Beach, Bay twin room

1 bedroom, 2 single beds, 1 bathroom

4–9 Oct

£1,578 total

+£186 Airbnb credit

Photo 1 of 29

Home in Southampton

Vogue Editors Home, Featured Hamptons Mag, Elle D.

4 bedrooms, 4 beds, 7.5 bathrooms

11–16 Oct

£2,743 total

5.0 out of 5 average rating, 7 reviews

Photo 1 of 29

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

1–6 Oct

£6,712 total

Free cancellation

4.96 out of 5 average rating, 45 reviews

Photo 1 of 18

Home in Sag Harbor

Striking Waterfront 3 Bedroom on Sag Harbor Cove

3 bedrooms, 4 beds, 3 bathrooms

17–22 Oct

£2,033 total

5.0 out of 5 average rating, 3 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

£7,892 total

4.99 out of 5 average rating, 148 reviews

Photo 1 of 29

Home in East Hampton

East Hamptons 3BR Private +Den Private Entrance

3 bedrooms, 2 queen beds, 2 bathrooms

1–6 Oct

£1,575 total

Free cancellation

5.0 out of 5 average rating, 3 reviews

Photo 1 of 20

Home in East Hampton

Remarkable East Hampton Getaway with Pool

3 bedrooms, 3 beds, 3 bathrooms

1–6 Oct

£1,492 total

5.0 out of 5 average rating, 3 reviews

Photo 1 of 29

Guest favourite

Home in Peconic

Provence on the North Fork

3 bedrooms, 3 beds, 3 bathrooms

1–8 Oct

£12,905 total

Free cancellation

4.95 out of 5 average rating, 37 reviews

Photo 1 of 29

Top guest favourite

Home in Clinton

The Connecticut Cottage | Historic Modern Charm

2 bedrooms, 2 beds, 2 bathrooms

11–16 Oct

£1,370 total

Free cancellation

4.97 out of 5 average rating, 32 reviews

Photo 1 of 29

Top guest favourite

Cottage in East Lyme

Beach Cottage!

2 bedrooms, 2 queen beds, 1 bathroom

25–30 Oct

£1,005 total

5.0 out of 5 average rating, 64 reviews

Photo 1 of 29

Luxe

Home in Montauk

Montauk modern 7-bedroom Heated Pool & hot tub

7 bedrooms, 10 beds, 5 bathrooms

1–6 Nov

£6,055 total

Free cancellation

5.0 out of 5 average rating, 42 reviews

Photo 1 of 18

Home in Orient

Brand new 4 bedrm 4.5 bath home with pool & beach

4 bedrooms, 5 beds, 4.5 bathrooms

6–11 Oct

£9,382 total

5.0 out of 5 average rating, 3 reviews

Photo 1 of 15

Top guest favourite

Home in Old Saybrook

Best of both worlds!

3 bedrooms, 4 beds, 2 bathrooms

12–17 Oct

£1,376 total

Free cancellation

4.92 out of 5 average rating, 119 reviews

Photo 1 of 29

Superhost

Home in Old Lyme

Connecticut Beach Home

Business host

10–15 Oct

New place to stay

Photo 1 of 24

Top guest favourite

Home in Montauk

Oceanfront Home Downtown Montauk

3 bedrooms, 6 beds, 1.5 bathrooms

25–30 Oct

£6,530 total

4.91 out of 5 average rating, 35 reviews

Photo 1 of 29

Top guest favourite

Home in Old Saybrook

Waterfront Oasis 4Bdr/2b

4 bedrooms, 4 beds, 2 bathrooms

19–24 Oct

£2,498 total

5.0 out of 5 average rating, 19 reviews

Photo 1 of 19

Guest favourite

Home in Greenport

Walk to Beach or to Town …

3 bedrooms, 4 beds, 2.5 bathrooms

4–9 Oct

£2,066 total

4.89 out of 5 average rating, 44 reviews