Like another comment said, there aren’t many options for hotels besides a bed n breakfast here and there. Check out Airbnb. I would bet Torrington would have some options, but it’s def not the shining gem of NW corner if you catch my drift. Kent’s my home town and was an amazing place to hike around all my life. Also look in Sharon, Cornwall, Salisbury/lakeville, north Canaan and even Millerton or Amenia NY

Check out Lions head and Bear mtn in Salisbury, Mohawk State Park in Cornwall, Bulls Bridge, kent falls and Macedonia State Park in Kent. Just following the AT is an amazing experience (particularly between bulls bridge/10 Mile river in Kent and pine knob loop trail in Cornwall, but that’s hometown bias), it has plenty of views and goes from mountain tops to the Housatonic River and everything in between. Hope this helps and enjoy!