I am trying to plan a 3 day wedding weekend on the east coast. Looking for a venue that can host about 150-200 people depending on how far away it is, with on site accommodations for about 100 people and a pool. Very flexible on location we live in CT but also playing with the idea of destination wedding like Maryland, Virginia or really any where that would be a cheap flight and an affordable venue.
Re: Wedding weekend venues
We got married at Mohonk Mountain House in NY. I can't recommend it enough.
From there, start to look at locations that work with the budgets and schedules of your guests.
I've been to a lot of conventions in the Nashua/Boston area. Cheap flight into Manchester and there are tons of venues. I'd recommend looking at Convention venues in the area for 150-200 attendees then start picking up the phone. Check the Barnum Museum in Connecticut as I believe they hire out for events though lodging wouldn't be on-site...
FWIW as a CT native I'd stick to what I know in state. If most of your guests are here then the next benefit is that they don't have to book hotels if they don't want to and then they can pick and choose what things to attend.