We are living in our vacation home that we bought when we had a mortgage on our first home and 4 kids in college. Yes, there were days that we called this place a money pit, but so glad we were able to move here when DH retired!

We bought this knowing we would move into it when kids all done with college. Bought in 1998 and moved into it in December of 2006. Hardest part was selling the old place, that was when prices were dropping. Now this place is paid off. We have put on 2 roofs, 2 A/C's, 2 furnaces, redid the bathroom and kitchen too. Added on a 3 season room and an extra 2 car garage (needed place to put the toys, pontoon, jet ski, etc.) Next is new windows.

We are both happy here. The one thing to look at if this is the place you plan on moving to for retirement is medical. Are there hospitals and doctors available? We have several specialists that we have to drive 2 hours to see, but have a great PC that is only 5 miles away. That is the biggest trade off.

My vacation home is in a Covid hotspot ;-) Aside from that, no regrets. I doubt we would move to our vacation home in retirement, but who knows, though my husband is unlikely to ever truly retire. He loves his work too much. At any rate the ski house is near a major city (SLC) with plenty of amenities, so we could theoretically.

We built a nice cabin but have not been there for about 4 years. I told son to sell it but with covid, it's still ours. Son goes and cuts the grass.

We bought a camp up north this summer. 2 hour drive from us. We spend the weekdays at camp and the weekends at home. So far no regrets.

Not buyers remorse, but remodelers remorse, after putting on an addition that about doubled the space. I wish we had torn the whole thing down and built all new.

I’d rather rent a place and let the owner worry about upkeep and expenses. However I can see the appeal of being able to pick up and go there any time you want, sleep in a bed that is just for you and be surrounded by your own things.

I'd much prefer to put all my energy and resources into one home. A vacation home is no vacation. It's just another place to cook and clean. Unfortunately, my husband has a "weekend" home that he bought about 12 years before we met. We used to come up here maybe one or two nights every month or two. Whenever he asked my preference, I'd always choose to stay in the city. But we moved up here mid-March and now he wants to stay here until there is a vaccine. I'll be so happy when this "vacation" is over and I can go back home! And if he said, "Let's go back sooner," I'd be packing before he got the words out.

I agree with dedtired if the place was far away I would rent and families sometimes just don't have the time to use a second home. I have a friend that has 3 homes. 2 are within 2 hours of each other and the 3rd is a beach condo in SC where she has to fly. She bought the condo to mostly winter over in. Personally I would rent a place in a warm weather state for 3-4 months than own and have it sit empty the remainder of the time. We thought off and on for years about getting a 2nd place, but the timing was never right. When the kids were at home between school and weekend activities we wouldn't have had the time to use it. Then after they flew the coop we were both still working full time and again wouldn't have had the time to use it. Now was the right time since we are both retired and have the time to use and enjoy it.

Dedtired, I totally agree with your on offloading the upkeep, otherwise there is nothing vacation like about the house! We don't have to take care of our place at all. There is a managment company we hired for that, however, there is no room service, and that folks is a big part of what a vacation is for me.

When the kids were at home between school and weekend activities we wouldn't have had the time to use it

This is the reason we bought the ski house. When my children were little, an woman whose children were already in high school and college said that having a place away from the usual activities was the key to getting to spend time with your kiddos during break times. Otherwise, she said, the children get busy with all kinds of stuff and no time is spent as a family. She suggested making sure you had a beach or ski type family trip every year to ensure plenty of togetherness. That has been sage advice for us. I am so glad I listened to her ( no need for your own place to follow her advice.)

We bought a vacation house in Cathedral City (Palm Springs adjacent) and had intended to rent it out through AirBnB or VRBO, but the city put a moratorium on new STVRs two weeks after we closed, and now the city is not even allowing renewals of old STVRs, thereby phasing them out completely. We should have bought in Palm Springs, but we were able to get a bigger house with a bigger pool in Cathedral City, and it is only 10 minutes from Palm Springs.

We renovated the bathrooms (no regrets there) and resurfaced the pool so that it is like new, but now we have no income from the property, and I am going to have to find another way of getting additional income.

Since we cannot rent it temporarily and do not want long term renters, we are spending about half of our time there now, which has worked out well for the pandemic, since Kevin is working from home now, and he can just as easily work in one house as the other. The bad thing is that utilities are expensive, and then there is also the property tax.

When we first bought our vacation home 20+ years ago, we used it almost every weekend. It was a great place for our children, extended family and friends. As time has passed, we work more and use it far less though we do have a great group of friends who own proerty near us.

Our original intent was to split our retirement time between this vacation home and travel. The major issue is medical. The closest hospital is an hour away and over the years our experiences with that hospital have been less than stellar.

We have made the decision to age in place rather than move to the vacation home. At some point, we will probably sell the vacation home but we aren't there yet. I still love going up there for the tranquility.

One thing I will point out is we have used our vacation home as a sort of refuge. Immediately following he 911 attacks, we packed up the kids and headed north passports in hand. Our vacation home is very close to the Canadian border so we were ready to visit relatives in Canada if things got bad here. With Covid, the house has given us a place to go to relax and get away. We pack all our groceries and do not venture into town or interact with other folks. We stay at the house contained and hike our own property. It has been a mental health booster.

I bought a house in a beach town about 5 years ago now. We plan to retire to that town in a few years, so I wanted to test the waters to see if we'd really like it there full time.

I don't regret it. However somehow it always costs more than you expected. Between the expected ongoing carrying costs, and the eleventy- million UNexpected costs it can be a expensive endeavor.

If I know then what I know now, I likely wouldn't have bought what we did, and when we did it. But that's part of the fun of 20/20 hindsight too.

In 2001 we were building a new home north of Chicago when a rental property we'd had on the market for ages...sold. We invested in a 1 BR 2 Bath Ocean View condo in South Maui in a complex where we'd vacationed the previous year. Bought it sight-unseen. The owner agreed to update the then-10 y.o. condo -- put in tile flooring, new appliances, water heater, some new BR furnishings. We flew out in February, closed on the condo and vacationed in it. (Now we've replaced everything all over again, both here and there. Home ownership...it never ends!)

Now we're selling the condo. It was *lovely* and great fun, but we aren't interested in continuing to rent it (Vrbo), and due to my health, Hawaii isn't as good a fit as *home*. If we don't get a good-enough price, we can rent it to one tenant for a year and wait until Covid says bye-bye.

Wanna buy a vacation home on Maui? You can still buy *direct* for a few more weeks! haha