I was just up in that area a week ago .and am returning tomorow.
The leafs were at prime in someplaces but over everywhere. In the 2 weeks time your going I don't think everything will be over.....some areas may be--but I don't think everything will be gone and done at that time.
In the KENT area --cross overs are3422 toto343 / 41 to Route 22.But I'd travel farther South in Connecticut to BULLS BRIDGE and cross over in Gaylordsville Route 55 to Route 22 NY.
Crossing at the Danbury Area--brings you to the beginning of Route 22 NY ---so at that point you'd need to travel NORTH..The connections in Ct. would be via 84 or Route 6 along with many other small roads that cross over as well.
2 nights rooming can be taken in so many locations its hard to tell you where. It all depends on where you enter your foliage routes , whether you plan to be in Connecticut or New York at dinner / room time.
Danbury has a slew of offerings as far as hotels go...and the Kent area/Litchfield Areas have has B &B's as well as motels.
Roue 22 in new York at the base of 22 have some well known Hotels and Motels..and along the length you'll find several sorts of lodging in small motels / Hotels and B & B's.
So , to narrow this down--you need to make a basic driving plan and THEN try to set lodging most likely near to or at your dinner location.