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If I purchase a second Peloton bike, do I need a second subscription?

It depends. You may have two bikes on the same Peloton subscription, but they can not be ridden, or logged into, at the same time.

If you have two houses, a bike at each house, and there will never be overlap of people riding them, both bikes may share the same Peloton subscription.

If you have two bikes, either at the same house or at two houses but people may be on both at the same time, each bike will require its own subscription.

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