Hey Sompurna, Dharamshala and Dalhousie is an excellent choice for winters. You need around 3 days in Dharamshala and Mcleodganj. Day 1: You can explore Dharamshala on bikes or cabs. Visit HPCA stadium, Tea gardens and Kangra Fort.
Day 2: Go to Mcleodganj, you can visit places like the local market, Namgyal Monastery, St John's in the wilderness and Bhagsunaag. Day 3: Dont miss out the sunrise, Start your trek early. There are two routes to do Triund trek, opt the normal route as the other one is quiet difficult in winters. You would be at the peak in about 4-5 hours. Enjoy your time there and start for descend. Camping on Triund in winters is possible but I wont suggest but if you are looking for camping experience you really should go for it as it would be an breathtaking experience. Day 4: Go to Dalhousie, you can opt for visiting local market or a small trek to Kalatop or the Ganji Pahari,
Day 5: Khajjar has to be the top destination to visit in Dalhousie and boy in winters it looks like Switzerland for sure. Enjoy the heavy cloud layer of snow and a frozen lake in the winter. Hope, I answered all your answers and feel free if you need anything more.
HI Sompurna, You can travel to Mcleodganj and do the Triund Trek. Spend a day exploring Mcleodganj and then head off to Dalhousie. You'd need about 5 days in total to cover all of it, and if you have more days, nothing better than that! Here's a rough itinerary that you can follow - Day 1 - Reach Mcleodganj. Explore the town, visit the Dalai Lama monastery and Naddi sunset point etc. Day 2 - Go for Triund Trek and overnight Camping. Day 3 - Return back to Mcleod and travel to Dalhousie. Day 4 - Explore Dalhousie. Day 5 - Check out ad head back :)