Still On My Bucket List
Best to use www.tripadvisor.com to find deals! If you have points through travel you can book directly through the hotel itself. Some of these places are great for summer road trips, others are great during school break in the dead of winter! I always look for the biggest bang for my buck. And a nice hotel that offers a great breakfast and an indoor pool when I'm traveling in the winter. Always make sure you filter your search to get what best fits your needs.
Boston, MA (Perhaps can go in the summer. Spend two nights here and two nights in Cape Cod. Kill two birds with one stone.)
Montreal and Quebec City
Camelback Resort or Kalahari (check www.groupon.com for occasional deals)
Cape Cod, MA (Perhaps can go in the summer. Spend two nights here and two nights in Boston. Kill two birds with one stone.)
Lake George, NY (Sagamore, Surfside on the Lake Hotel & Suites, Comfort Suites, Marine Village Resort) (Worth doing this and Montreal in one trip)
Lake Placid, NY (Definitely worth doing this and Montreal in one trip. Also some nearby waterfalls you can swim in)
Newport, RI (I've been told it's nice during Christmas. Much less crowded and less expensive. Mansions all have Christmas decorations. But it's definitely the nicest during fall foliage the peak of which is the last two weeks of October)
Washington DC (best time is Spring during Cherry Blossoms)