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Hakone - where to stay for two nights

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We will probably be coming from Matsumoto to the Hakone area (this is not confirmed yet as I had planned to go to Takayama from Tsumogo, but am running into the festival in Takayama for the nights we wanted). Even after reading trip reports, etc. am still a little confused about where to stay for two nights. Most people seem to come for the day or one night.

From what I've read, Gora seems more relaxing. We're coming for the scenery and walking/hiking rather than nightlife. Should we stay at the same place in Gora for both nights?

Also, do you have recommendations for a ryokan or inn in Gora? We hope to spend $350 (about 40.000 yen) or less for a room with dinner. Can see that Hakone area is very expensive, so we can stretch that for the right place.

We should buy the Hakone Pass, I think. Where can you buy it in Hakone?

Any other advice will be very welcome!

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