Travel
The Inn at Pine Plains is the only one in town. If you're looking to stay nearby and the Inn is booked, there are usually a number of houses available on Airbnb and VRBO (including one or two on a tiny island in the middle of the lake!).
Towns within 20 minutes of Pine Plains include: Ancram/Ancramdale, Clinton Corners, Milan, Millerton, and Stanfordville. Towns within 30 minutes include Hudson, Red Hook, Rhinebeck, and Sharon CT.
If you are flying in, closest airports are Westchester NY (HPN), Albany NY (ALB), and Bradley CT (BDL).
The closest MetroNorth train stop is Wassaic, the last stop on the Harlem line (~25 min from Pine Plains). The second closest is Poughkeepsie, the last stop on the Hudson line (~40 min from Pine Plains).
Hotel
The Inn at Pine Plains
3036 East Church Street, Pine Plains, NY 12567
Hotel
The Millerton Inn
53 Main Street, Millerton, NY 12546
Hotel
Beekman Arms Delamater Inn
6387 Mill Street, Rhinebeck, NY 12572
Hotel
Whistlewood Farm Bed and Breakfast
52 Pells Road, NY 12572
Hotel
Jenny's Country Manor Lodge
1639 New York 199, Stanfordville, NY 12581
For all the days along the way