Flight
Closest airport to Woodstock is Albany International Airport (about and hour from Woodstock) Newark is two hours (you don't have to cross the George Washington Bridge) . JFK & LaGuardia Airports are two and half hours depending on traffic and time of day (could be three hours).
Train
This is an option for travelers that don't want to drive and are staying in the city. Amtrak is easy and comfortable. We don't have trains on our side of the Hudson River. However, the Rhinecliff station is about 30 minutes from the center of Woodstock. Rhinebeck is a cute town worth exploring!
Travel Note
Another option from Manhattan to Woodstock is taking the bus from Port Authority. I've taken it many times visiting Michael and it's easy, safe with convenient departure times. Trailways makes stops in Kingston, Woodstock and Phoenicia.
Hotel
There are lots of options to choose from and we've narrowed down to what feel is best for our guests. The Emerson Resort & Spa is the most traditional (picture shown at the top of this page). A full service hotel with a bar, restaurants, pool, spa and gym. Please call them to book (they're upgrading their online booking system) . Woodstock Way Hotel, a contemporary hotel in the heart of Woodstock. Airbnb; there a 600+ in a town with a population of 6,000!
Hotel