Things to Think About Before Buying a Vacation Home

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If planning vacations are stressful for you, maybe it’d be better if you bought a vacation home, a little place to get away from it all. Some considerations.


It’s the season for vacations. From cross-country road-trips to backpacking with the family, there’ll be vacations of every kind popping up in your Facebook feed for months now.

Just recently, I’ve enjoyed watching friends of mine buy a cottage on a little island, followed by a boat. With two young boys, I’m sure they see years of fun ahead of them as they take family weekends and summer holidays over on their little island. A tire swing has already been hung, so I’d say they’re well on their way.

If you’re looking for an investment that can add real value to your family as well as your portfolio, you might want to consider a vacation house. We’re not talking extravagance here. This is about getting a nice, small place off the beaten path a couple hours from home.

Here are some things to think about if you’ve had a vacation home in mind:

Know the area

Vacation homes can take longer to sell for the very fact that they’re often not in live/work areas, so it’s important to know you’ll enjoy committing a considerable chunk of your future leisure time there. Do you like the surroundings? Is getting there easy enough? Because I guarantee you, if it takes more than two hours to get there, you’ll have excuses to avoid it.

Beyond that, have you looked into development plans nearby in the coming years? Does it jive with what you’re in search of?

A vacation spot should fill you up and prime you for a return to work and life. It needs to be restful, beautiful, and practical for reaching. Make sure the region fits those bills.

Be hip to the bucks

Purchasing a vacay home is almost the same as a normal home purchase — you’ve got closing fees, immediate maintenance, and all that. If it’s in a remote area, your moving costs will be higher than you expect, likely. If it’s on an island like my friends, can you afford boat trips or better yet, buying a boat? When you’re not around, there’s the risk of crime — since where better to rob than vacant vacation homes?

You’ll likely need security monitoring, good insurance, maybe a property manager to take care of things when you’re not coming by for weeks or months on end. Maybe you want to make some money in the off-season and list it on AirBNB for short-term stays, in which case you’ve got to spend money to make money with the help of a trusty caretaker.

It ain’t a hotel

Unless you’ve got a local cleaning lady you can pay to drop by before you arrive for your vacation stays, you can expect housecleaning when you show up. And then it’ll be wise also to keep a list of the little things you’re noticing when you’re there. Loose roof shingles? A low-hanging branch making you wary? Leaky pipes? These are all things you need to deal with when you see them, because being absent when things go awry means it can spiral into a much bigger problem before your return.

Those loose shingles blow off in a big storm, the rain comes pounding down, maybe you go from just having an afternoon of shingle-fixing right into a full-blown roof-patching and water-damage repair inside — after a month or two months of not coming back for visits, which means mold sets in.

It’s an investment, it takes work, and it’s important to know that before you commit. But if that’s the kind of work you enjoy when you have the time to do it, then it’s part of the vacation home charm. Ownership is fun, for some of us.

A great life, if you want it

A vacation home is a big investment that can save you a lot over the coming years, all while building your family fun factor up. Trips abroad might give you amazing experiences, but it’s money spent you’ll never get back. The time and investment in a family vacation home will always come back to you — and it can be something wonderful you leave your children long in the future.

The greatest vacations of my childhood were always when we stayed in a cottage someplace for a couple weeks. There’s something about a home-away-from-home with nature and the good life just outside the door. It’s a magical place for children and a wonderful family time, and for kids, it’s often gold.

It comes down to the kind of person you are, what you consider relaxing, and how much you really want to just “be” with your family and nothing else. Maybe this is the summer you find the vacation home of your family’s dream.

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