As long as there has been a New England, there have been tiny summer cottages.
During the later 19th and mid 20th Centuries, summer get-away communities in the Berkshires, White Mountains and Green Mountains, lakeside, river and oceanside, grew like wildfire. They were unique in their construction (and being all wood built with few safety codes, many also went down in flames). They were built for seasonal living and if they're still standing, these 2x4 stick-built and log tiny cabins are still be enjoyed in MA, NH, ME, VT and upper NY State.
In past generations you didn't have to be rich for this seasonal home. Even people of modest means could buy a small piece of land and set a tiny cabin on it, often leaving the "landscaping" to nature. As all good [and bad things] this opportunity to escape the business of suburban or urban life has changed. This possibility is no longer as simple. Building codes now apply at least to some extent where they didn't in past decades (and rural inspections were, we might say, a little more challenging to keep up with when the "up country" towns' populations were in the 100's).
The idea of a tiny summer cottage appeals to you?
You have a few options. The ease of each will depend on the zoning where you would like to summer, and you'll have to discover that yourself through any given town's zoning bylaws and local building codes (usually online):
1. Purchase an existing seasonal cottage
2. Build a cottage that meets the codes (sometimes seasonal cottage codes are much more lax than yearround homes. Research the towns!)
3. Build or Purchase a tiny house cottage on wheels. Tiny House Northeast can design-build the perfect 12-32' CoyWolf Cabin suited for your particular situation; single, couple, roommates, disabilities, familes, with pets. Just skip the horse. We can build a shed for the horse. And a fancy chicken coop too!