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3.
A low-budget hotel/motel that Sam and Dean Winchester of "Supernatural" would stay in. This kind of place may be rent by the hour, unkempt, even occupied by cockroaches.
That place was a total winchester. We are never staying there again
by stillaninnocent July 31, 2011
 
1.
The surname of characters from the CW hit show, Supernatural.

Winchester means family and family means nobody gets left behind.

Except Adam.
Adam: "You came back."
Dean: "You're family Winchester spirit GO"
by gagcaster January 20, 2013
 
2.
the last name of the hottest, sexiest, badass brothers on TV, Sam and Dean
Girl1: omg omg omg look
Girl2: OMG THEIR SHIRTLESS *drool*
Girl1. soo hott
Girl2 i know,i love sam and dean Winchester
by pogo_hammer June 25, 2011
 
4.
a lever-action rifle origanlly made in 1866. bassicly a musket that you could fire multiple times before reloding.the same company that made the winchester also made a lever-action shotgun.
the sherif cocked his winchester, adn shot the man in the head.
by pvy.takahashi September 02, 2008
 
5.
A town in Hampshire in which the presence of an expensive school means that students of said school think they are incredibly posh and residents not attending this school think they are from coal-mining families in South Shields when in fact most of them, students and non-students, are just varying degrees of middle-class
Winchester College student: "No, let's not go to McDonald's, all the chavs will have just finished school."

Non-student:"Don't you hate those posh twats from the College? They think they own the place just because they're upper-class."
by admiralsnackbar January 13, 2011
 
6.
A small city in Hampshire in the south of the UK. Famous for its cathedral, Winchester College, and was prevoiusly the capital of England, under King Alfred.

The rifle and the American town are named after Winchester
I live in Winchester.
by dcl211293 March 10, 2010
 
7.
A Winchester is a person who retells the same jokes over and over again. It started off as a nickname for a person (We'll call him Dev) who would repeat the same jokes on a regular basis, especially on a Jokes page on Facebook. The name comes from the lever-action rifle of that name - this was often called a 'Winchester Repeater'. The nickname stuck and even to repeat a joke now is met with claims of 'Winchester!'
Winchester! You told us that joke about 3 months ago.

That's a Winchester - heard it before.
by Grollope July 12, 2013