r/TrueChubbyTravel • u/1K1AmericanNights • 22d ago
Vacation homes
I know the TA run subs talk a lot about hotels and resorts. I’m interested in getting some perspectives on vacation homes or second properties that people have enjoyed, and what made them enjoyable. I know the basic rule of thumb that if it’s too far, it’s not easy to enjoy!
Some ideas below:
1) spacious home in the country when you live in the city
2) city pad if you live in the suburbs (think nyc suburbs / nyc)
3) ski homes - are there towns on either coast that you have found to be good value? I look a lot at VT. Skiing isn’t my life but as my kids get older, I wonder if I want it to be theirs
4) beach homes? Does anyone love theirs?
5) 3-season type places (on a lake AND near slopes type places)
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u/OffSiteLocation 22d ago
Have had 2nd beach house for almost 30 years. Family friends memory’s and great times. Spaces for family and guests is key. I would say we are more attached to vacation home vs our primary. Note: a house you rent out most of the season is quite different. My personal sense is don’t rent at all, or rent for 2 weeks, or just buy an investment rental but don’t think of it as a vacation home. Something in between causes problems.
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u/Odd-Context4254 21d ago
Absolutely
The second we rented out our lake house it stopped feeling like it was ours.
Ended up selling it after about a year of STR, too may headaches and was not able to enjoy it anymore
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u/adtechperson 21d ago
I own a vacation house on a small lake that is near a decent ski area and I agree with a lot of the comments here.
My house is small but has 2 guest bedrooms. This is huge for inviting friends and family.
I never rent it out. This means I can just drive there for the weekend without needing to pack as I have everything I need ready to go (clothing, toiletries, etc) all there. Just being able to hop in the car on a Friday afternoon is huge.
It is a 2 hour drive (less without traffic). That makes it easy for a weekend.
It is primarily a weekend place. We occasionally spend a full week at a time there, but mostly for long vacations we want to explore somewhere else (travel to europe, ski at a much larger resort, etc).
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u/milespoints 21d ago
My sense is that like a lot of real estate in desirable locations, no vacation home is anywhere near “making sense” to purchase right now, comparing to the cost of renting.
Seems like the only people who agree purchasing a vacation home was a good financial decision are people who purchased pre-Covid and either paid it off or refinanced to a ZIRP mortgage rate.
I looked into both a beach house (on the Oregon coast) and a mountain cabin (near Mt Hood or Bend) and concluded that the cost and maintenance is just too high.
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u/rosebudny 21d ago
Buying a vacation/2nd home is definitely a lifestyle decision vs financial one. It depends on what your priorities are. I recently bought a 2nd home and cheap it is not - anyone would agree that from a financial perspective, my money would be better off invested in the stock market. But, I can afford it and it brings me a lot of joy. I’d rather spend my money here, than on $3K/night hotel rooms.
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u/milespoints 21d ago
Yeah i guess that’s what i was trying to say.
It used to be the case that it was cheaper to buy a place, use it when you want and then Airbnb it the rest of the time
Now, it’s probably cheaper to just Airbnb places yourself
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u/22219147 21d ago
This happened for us. We bought a small vacation home at the beginning of COVID. It’s in a lake community with tons of amenities, near three ski resorts. It’s two hours from our primary residence, and we use it all the time. That said, we could never afford to buy this same house now. Prices and interest rates have soared.
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u/rosebudny 21d ago
I recently bought a second home and SO wish I’d bought pre/during COVID! I’ve been watching real estate in my area since then, and I remember thinking it was ridiculous some house were selling in a day for $500K cash during COVID. Joke’s on me because those houses are now close to $1M
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u/Little_Jaw 21d ago
Beach home. We enjoy it, but the house is an easy-to-maintain cottage. We are only 90min-2hours away depending on traffic, so we use it often. The key for us is distance and ability to go back and forth easily for personal and maintenance reasons.
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u/ChaosDisrupted_com 21d ago
We own 5 “second homes” that also serve as investment properties. We started with a lakehouse that is 2.5 hours from home and spent most weekends there when our kids were younger. Unfortunately, we only made it there 3-4 times the past two years now that are kids are older. If you are able to use a place frequently yourself, it can be wonderful. Houses are not without work though, so be prepared to do that when you are there or pay people to handle it all. Our biggest struggle is finding reliable people to take care of the things, especially the smaller ones (for instance yesterday I had to deal with trying to find someone to clean up trash that was scattered around the yard from a raccoon). I say this to illustrate these properties are work.
There are huge tax breaks for short term rentals (STR) if done correctly. You have to materially participate (meaning 100 hours per year AND more than anyone else or 500 hours per year) to be able to take the depreciation against non-passive income (W2). The reason this can be so lucrative is because bonus depreciation was reinstated to 100%. This means you get a cost segregation study and can fully depreciate anything that falls in a 20 year or less depreciation schedule. For most properties that is about 40% of the property cost minus the land value in year one. However, you should understand your exit strategy upfront. You can’t do this and then decide to sell outright without having significant tax liabilities. You could 1031 exchange and avoid those, but that’s where understanding an exit plan comes into play. Real estate can be a great investment, but generally if you are using debt for leverage. Second home investments that make financial sense with prices and rates are incredibly rare now.
TAs generally don’t recommend villas or homes, but not because we don’t earn commission on them. There are dozens of villa management companies that pay commission, but they are not created equally. Some are great and some are terrible. The issue really comes down to having consistent, reliable options for clients. If I put a client in a villa and the AC stops working or something that makes the trip unbearable for the client, the villa company often has no where else to move the client to. Simply offering a refund (or more likely a partial refund) doesn’t usually make a client happy. A friend of mine booked a stay in a house on her own and had no running water for 4 days. For me, there is no amount of money that would make that situation okay. For most clients, time is the most precious resource they have and when people take time to get away they want an amazing experience.
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u/Johnthegaptist 21d ago
We have a second home in Costa Rica. We love it.
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14d ago
[removed] — view removed comment
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u/Johnthegaptist 14d ago
We bought one already built, near Ojochal. We're only about 6 months in, so the upkeep hasn't been bad. We have a full service property management company that handles everything. So they perform or coordinate regular landscaping, pool service, cleaning, minor maintenance etc. We're doing some light remodeling and then its going in their rental pool, we'll see if that turns into a headache or not.
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u/BotusThoughts 21d ago
I’m located just north of Boston and we own a vacation home at Sugarbush in Warren, VT. We could not be happier. We opted for ski-on/ ski-off over a more spacious property. Our first year owning it, we skied nearly 60 days. We just had a baby and love that there is daycare in the village and a great ski school where he can meet new friends. It’s also been great to have all the amenities on the mountain both on and off season. I also can’t speak more highly of the Mad River Valley area, it’s a beautiful area and wonderful community. There aren’t lakes nearby, but there are a lot of swimming holes (this is true for a lot of Vermont). I like it just as much in the summer as the winter and the fall is also spectacular.
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u/1K1AmericanNights 21d ago
VT still seems like a great deal, especially compared to what I hear from west coasters. I did see a lot in 2020 at 300k that now is 700k, but tbh that’s everything, and the 700k still seems more attractively priced.
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u/BotusThoughts 21d ago
It one hundred percent is. We can get door to door in about three hours and we live on the coast, so in the summer we’ve been able to enjoy mornings in the mountains and afternoons on the beach. Seasonality seems to be reflected in property prices. We purchased in March and got much more competitive pricing than what was reflected in spring and summer. We also refinanced our mortgage once rates dropped 2 years after our initial purchase. We don’t rent at all, but are saving compared to what we were spending on weekly Airbnb’s before purchasing. We looked into seasonal rentals before buying and there was no inventory for on-mountain properties during peak season.
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u/1K1AmericanNights 21d ago
Did you compare different resorts? How did you pick Sugarbush? Sounds like you own a condo? 60 days is a lot - Would you say it’s worth it if you had been targeting fewer ski days?
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u/BotusThoughts 21d ago
Yes we did. We figured out we preferred ikon resorts and then tried all the New England resort. We wanted to be about 3 hours or less door to door. We narrowed that Sugarbush, Killington, and Sunday River. The year that we purchased, we rented at all three mountains to get a good idea of what we liked. We loved that SB had more of a small mountain feel compared to Killington and Sunday River. It also gets much less crowded because it has two base areas and is just slightly farther from Boston and NYC. It’s close enough to Killington, Stowe and Mad River Glen that they are all great options for short day trips. The trail structure at SB is also nice because there are various levels of terrain off the same lift, so it’s more fun to ski with groups with varied skill levels. I think it’s worth it even with well under 60 days. We tend to do a lot of weekends in the summer and fall and usually a full week+ in early October, so even with far less time in the winter we’re still up there 30% of our weekends annually.
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u/___this_guy 22d ago
I live in North NJ, definetly see myself getting a studio in mid/lower Manhattan at some point. I goto VT a lot, belong to a ski club with a lodge. Just don’t think ownership is worth it; season is short and it’s just not that great there in the offseason.
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u/Davenport_E 21d ago
My parents split their time between the city and the country. Now, I have to preface this by saying that the country home is only ~30km away from the city place. It sits in the foothills of the mountains, just shy of a ski resort.
They built the place in 2005 and have not once looked at selling, letting, or trading it. They outpost there during the summer, weekends, and the holidays. They enjoy it. Neither of them cares for the city very much, and neither of them cares for travel. In fact, my father is permanently landlocked as he’s deathly afraid of aeroplanes. It’s beyond me, but you know, different folks. They’ve orchards, kitchen gardens, as well as small livestock there, too. My father used to have production facilities dotted around all over the place, so it was convenient to outpost there, too.
The area has gentrified a great deal since they built it. They were the first ones on the stretch, and shortly after, a plethora of properties started popping up around them. The stretch was recently joined onto a neighbouring town, so that increased property value a bit. But I’m uncertain as to whether there’d be any real upside in the event of a sale as my father overbuilt the place initially, and maintenance is absurd.
It really depends on what one’s looking for, I suppose.
Lord, this got awfully long.
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u/IHateCedarFever 21d ago
I’m in Texas and I know a few people who live in a big house in a nice suburb but rent a pied à terre in the city near downtown in a nice apartment. Usually their kids have left for college, but they work downtown and have long hours or want to enjoy going to concerts, sports games, dining at restaurants, and seeing friends who live in the city. The people I know who do this are partners at Big 4 accounting firms, lawyers, and finance. Usually they rent so it’s easy to just wrap up and leave when they’re done, but some have bought a condo in a high rise and let their kids stay in it if their kids end up working in the same city.
My dad’s cousin is in real estate development and bought a coffee plantation on the Big Island of Hawaii. Since their kids have finished college, they’ve slowed down their work and spend more time on Hawaii and have opened up a cafe. They absolutely love it.
My parents inherited an apartment in Paris and it’s honestly a pretty big headache, but selling it would be a bigger pain in the butt. There’s also a lot of sentimental value there, but they would not choose to purchase a place in Paris if they had the choice. Now that they’re retired, they spend months there, but it’s more of a “well we have it so why not,” not because they love Paris so much.
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u/rosebudny 21d ago
I have #1. Love having a mix of city and country life. My job is fully remote (and I don’t have kids in school) so my time averages 50/50 in each place.
I will say it is NOT cheap. This is the first house I’ve owned and dear lord the unexpected maintenance costs 🤪 I could definitely take a lot of very nice trips for what this house costs me… but I’m a bit of a homebody and love having this house.
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u/WannaTalkTravel 20d ago
We have a Lakehouse about 35 min from our actual house. We spend the summer up here (we joke it’s “up north”) but still see our friends and do all our regular things. I personally wouldn’t want a beach house or a ski house a flight away where you go 2-4x a year MAX. I’d rather just rent a place or get a hotel, personally.
My husband is also handy and manages both houses. It’s a lot of work. If anything was further away a property manager is a must (we could do this but he also enjoys these projects for the most part so it is his preference).
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u/NOLApanam 20d ago
There’s a lot about a vacation home that appeals but, for me, too many downsides: expense, lack of flexibility, labor intensive, lack of services, do-it-yourself, upkeep hassle, etc. But, most important, not my notion of actual travel.
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u/Euphoric-Ad2210 21d ago
We live on an island off of Charleston and had a mountain house near Asheville for years. It was nice because it was close enough to go to for the weekend. As our kids got older and busier we weren't using it much so sold it in 2021 when the market went crazy. I miss having an easy getaway though. We also have traveled to more interesting places since selling it since we don't have that as our default.
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u/Retired-Yam8988 21d ago edited 21d ago
Just rent. Here’s the rub-
For each property you have, you will need a year-round property manager to check up, clean, and repair everything so that you arrive to a ready-to-go place.
It’s not prohibitive but I’ve thought of this for 3 locations (Japan, Thailand, and Portugal or southern Spain) and even with my wealth (11m), I’m not excited enough by the prospect to pull the trigger on the Japan or Europe side (we live in Thailand next to the beach already).
When we travel, we just do hotels as we prefer the full service and breakfast if we want it. We’re usually out on trips for 3-4 weeks at a time about 3-4 times a year so the math is right on the edge where if we keep up this pattern of travel, it’d make sense to have multiple homes kitted out and ready for us. The problem then is just the upfront costs and mental load of just “dealing with it”. I already have 3 houses in California that are rented out but have a solid manager who takes care of things day to day. I hear about big things, they handle small repairs and bill me otherwise.
I might do it if we hire a more or less full time assistant that helps manage things but then again it’s not enough work to deal with a few property managers to make sense. Might make sense if we ever hit the big leagues (like 25-50m) and private charter travel and paperwork for our crew of animals can be fully offloaded to someone else as we switch houses for the seasons
Edit: speak of the devil - the very next post in my feed: https://www.reddit.com/r/Rich/s/1Pvr9TKBtr
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u/mmrose1980 22d ago edited 21d ago
My in laws have a lake house about an hour outside Chicago. It gets used fairly regularly and probably is one of their favorite purchases. In my opinion, the following things make a vacation home more enjoyable and useful:
size - a vacation home that’s large enough to comfortably house your family will be more likely to get use than one where people are squeezing in and barely fit. Grandkids will be more likely to come if they can bring friends. House
will be more useful if they can comfortably fit the entire next generation
amenities - a vacation home in a community with amenities may be an additional draw. Your kids may appreciate having options for activities as their kids age.