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Tourism and second home is an age old yet booming phenomenon in many parts of the globalized and neo-liberal world. The motivation behind investment in second home may varies from work, leisure, retirement, etc. and yet what remains common is the ‘sense of belonging’ generated by it. The ‘sense of belonging’ refers to emotional attachment and identification that individuals have with a particular social group, or geography as in this case. While the contemporary scholarships have explored the relationship between second home and ‘sense of belonging’ issue in a manner where the host community are the one with disrupted sense of belongingness with the influx of tourists themselves or their investments. However there are limited studies which talks about the phenomenological rationale behind the tourists’ investment into sense of belonging via second home despite their primary residence from where they already draws their rootedness and identity. Hence the aim of the current paper is to explore this phenomenon and bring out multiple stances of such investment ranging from motivations behind second home purchase to the diffusion of identity from ‘being a tourist’ to ‘being a native’. The research is rooted in primary data collected from hills of Uttarakhand state of India which are famous for investments in second home and retirement home. The data collected includes observations, interviews and case study which are witness to this change. The current study proposes that however it is immensely necessary to maintain sustainability in tourism sector so much so that the touristic destination does not end up becoming what the tourist leave behind in their search for tranquility but there is also a need to relook at binary categories of work-leisure, tourist-native, without undermining the criticality of the phenomena rooted in privileges of one community over other.