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Hi divya, winter season is best to visit pondicherry. If you are travelling from chennai then avoid rainy season of july and august as it is a flood prone area. For itinerary, you can go through the following post.
https://www.tripoto.com/trip/8-days-backpacking-trip-from-delhi-mahabalipuram-pondicherry-allepy-kochi-delhi-595a41883e084
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Hi Divya, you can consider visiting in the month of Oct or Nov, You can find lot of budget and premium resorts to stay. You can choose a sea facing cottage. You can stay around auroville, Don't miss to stay near the French Colony, Also try the wood fire pizza there.. Hope this helps a bit.
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