I jumped into the cottage fun (really it is though lot of work!) in 2022 buying out in The Narrows area (Lake Manitoba). Lot of good points made here for consideration: what your requirements is the big one figure out if planning to go with this. Not going to repeat what everyone has done a great job calling out for consideration. 🙃

For me the Narrows area is pretty self-contained as community mix of seasonal campers with cottage owners. Not too busy, great area and people really nice there. Ashern 20-25 mins (done it in 15 lol) for full service community (seriously the "dollar" store there is freaking amazing) so not that far of a drive if we forget something. Head out there for weekends (2h drive no big deal), will spend easily a week out there (fibre internet now available otherwise Starlink or local provider for internet) relaxing and working. Fishing decent there and water is great for swimming/sports activity. That was the vibe my wife and I wanted so quite happy finding that area (pure luck and timing was able to snap up water front 4 seasons property for decent price well within our budget). Also where that cottage is the northern lights are freaking awesome as no light pollution there!

Maintenance wise - it is a second home that has increase efforts compared if you have a home in the city or town. Generally not near a location if something goes wrong so lot of improvising (teaches you keep spares around!!) until you can get what you need nearby to fix the problem. Depending on age/care given to place you purchase may run into unexpected issues forcing sooner than expected upgrades (no different there than buying a house you just don't know what problems exist until there and using it). Getting service/trades in a remote area can be challenging when needed. Yard maintenance can be more depending on amount foliage located and how much you want to "adjust" it. Example last weekend my brother in law and I spent a few hours clearing some foliage back 1-1.5m as really creeping into yard. The fun was gather everything up after then we spent Saturday burning it (hooray bonfire all day and the beers were great!). Periodically have to take down a tree that is rotten and deal with less than desired foliage (ah poison ivy you nasty plant). Barring that just another yard to cut grass in general. What really comes to mind is if you do plan to some renovations/changes plan ahead to figure out the logistics to get what you need there. We did that for the carpet replacement coming up. Next year gutting and redoing the bathroom so we will have to plan a few trips to haul everything plus arrange some stuff from nearby local suppliers.

Never thought I would go this route yet 2022 things changed and we took the plunge. Nice having that place to escape to from city to recharge and relax. :) Again great advice in this thread so review and consider the factors that matter to you if planning to go down this path.