Flight
You have a lot of airport options; none of them are great. The obvious choices are flying to NYC or Boston and then renting a car to drive up. If you can find good flights into Albany or Hartford, those will get you a bit closer. Hey thanks for making the trek!
Hotel
Here are some hotel options: Old Inn on the Green (charming, historic inn from the 1700s; books up quickly in the summer); Gedney Farm (farmhouse chic); the Red Lion Inn (fun little inn with a pool); Fairfield Inn and Suites (you know the deal here). Old Inn and Gedney are basically across the street from the wedding venue. There are other options in the area, so let us know if you have any questions. We'll keep you posted if we end up getting a room block at any hotel(s). There are a ton of awesome rental houses in the area, many of which have lake access or pools. Check out Airbnb and VRBO -- these places book up quickly in summer so we recommend booking now. We'd love for as many people as possible to get a place on or near Lake Buel, where we will be staying. It's an idyllic lake with beautiful water and we can swim together! FUN!
Train
From NYC: take the Metro North from Grand Central to Wassaic and then taxi or arrange pickup. If you want to take Amtrak: take it to Pittsfield and then taxi or arrange pickup. THERE IS NO UBER UP HERE SO PLAN ACCORDINGLY :)
Travel Note
Phone service in the Berkshires can be very unpredictable. If you are driving up, make sure that your map is preloaded. If you are taking the train, call and schedule your taxi pick up ahead of time. Emerald Express Taxi (518) 592-1074 Taxico (413) 528-0911