Take Your Vacation or Cash Out the Vacation?

Updated on August 23, 2021

Whenever you change jobs, there’s always some vacation days left over that you can either take or cash out (some employers won’t give you an option, this is for those who do have a choice). For me, the choice has often been pretty clear: take the days off. You’ll be paid for both but by taking vacation you get a few more benefits.

The only argument I can think of in favour of cashing out vacation is one where you want to start work at your new job ASAP and you’ve signed some sort of non-compete agreement with your former company. In that scenario, you would be in violation of that agreement if you worked for your new employer while still on the payroll of the former one. Outside of that scenario, unless you all can think of one, that’s the only argument for cashing out vacation. (There is one more, if you have a lot of vacation and you want to be paid in the current pay cycle rather in the next one… but that’s even rarer than the first scenario)

Here are reasons to take the vacation:

Medical Insurance

If you take the vacation days, you still get medical coverage for the time you’re on vacation. If you get paid out for those days, your medical insurance ends on your final day. This may not be a big deal if you start your new job immediately. If you want a few days off in between employers, it pays to “take vacation” and have medical coverage.

One thing I never understood was why my medical insurance expired on the last day of employment yet I continued to pay, out of payroll deductions, for medical for the entire month.

Accrued Benefits

Depending on how your benefits math is calculated, you may want to schedule your final day during the beginning of a month. At my last employer, our vacation days were accrued on a monthly basis. When I left on February 28th, I didn’t get the vacation days I had accrued for the month of February (ouch). This may be the case for the accrual of other benefits as well, such as pensions, so you might want to take a few vacation days to pull you into the next month.


If you’re a few days away from a holiday, it’s better to take the vacation and get paid for those holidays (duh). I knew someone who switched jobs around Thanksgiving. Using his vacation from his first employer, he was able to stretch is last day past Thanksgiving. He also started at his new job on the Monday before Thanksgiving. End result was that he was paid by two employers for that nice two-day holiday… very clever!

One thing to be aware of is whether you signed any sort of non-compete agreement (as mentioned earlier) while you were employed with your former company. In the case of my Thanksgiving friend, there was no non-compete agreement in place (not that the first employer knew) and so he could technically be employed at the two companies simultaneously so all was okay.

Of course, this requires some delicate discussion with your HR department or your direct manager. I’ve found that people are reasonable, will appreciate some forewarning, and won’t mind you taking vacation. If your HR or your manager doesn’t seem reasonable (and everyone who has an unreasonable HR and/or manager knows they’re unreasonable), give the least amount of notice possible. It’s all business.

Start saving now for your vacation

Unfortunately, a summer vacation can get a little expensive. Whether you drive or fly, you need to come up with the funds to pay for your excursion. You shouldn’t go into debt for your summer vacation, though. You should come up with a plan to save up enough money for a summer vacation.

What Do You Want to Do?

Your first step is to figure out where you want to go, and what you want to do. You also need to decide how you’re going to get there. For a larger family, it is sometimes more cost-efficient to go on a road trip.

No matter what you decide, though, you need to estimate the costs. Research vacation packages and airfare online. If you are going on a road trip, AAA has a calculator that can help you estimate fuel costs for your car, depending on the gas prices in the areas you plan to travel.

Consider food, lodging, and other costs that you might incur as you get ready to go on vacation. When my family took a three-week road trip while I was growing up, my parents had to factor in the cost of doing laundry on top of other costs.

Put together a list of what needs to happen, as well as a list of things you can do to reduce your costs. Look for discounts on everything from admissions to attractions to hotels. Consider that you can save by bringing some of your own food, or by getting accommodations with cooking facilities (and then shopping at a local grocery).

Now that you know how much you will need to go on vacation, it’s time to create a savings plan.

Can You Save Enough for Your Summer Vacation?

You will need to develop a short-term savings plan if you want to save for a summer vacation. Once you know how much it will cost, you need to divide the total cost by how long you have to save until you need to head out the door.

There are companies offering short term loans just for this reason, a quick search brings up a slew of online lenders all vying to offer you cash for just such a reason. One I found Simple PayDay offering short term loans of up to $1000 to use just for this reason. One large reason to avoid this, however, is the extortionate interest rate and large repayment you’ll have to make when you return, undoubtedly putting a dampener on the holiday you’ve just returned from.

Start saving

If you figure that your vacation will cost $2,000, and you have four months, you will need to save $500 a month to make it happen. For those who want to go on a bigger vacation, it might make sense to keep this year’s “vacation” to camping and other inexpensive, short-term trips and then save up for a year. I know a family that goes on a big vacation every other summer. In between, they save up for 24 months to get the money needed.

Time to get saving

Determine the time frame that makes sense for you, and then get everyone involved in the savings effort. Many children are happy to contribute a portion of their earnings/allowance to help fund the trip. Keep the money in a high-yield savings account to help the money grow a little faster. You can talk about cutting back on unnecessary expenses to make the vacation happen, or you can look at ways to earn extra money.

A great way to save on your holiday would be to avoid a costly hotel. But don’t worry I am not expecting you to sleep on the beach, what I am proposing is using a short-term holiday let, like those found on AirBnB.

Why Skip the hotel and rent a private home

  1. It’s cheaper. It’s exceptionally cheap when you go during the off-season, usually almost 50% off the peak rates. The vacation homes are usually very large so when you finally calculate the cost per person, it’s quite affordable.
  2. It’s negotiable. Hotels are not very good at negotiation, unless you’re a savvy customer or use something like Priceline, the price is whatever you can get through a travel search site. Demand for vacation homes, especially in this recession, is down and you can use it to your advantage.
  3. You have kitchens and grills to cook yourself. Most hotels, unless it’s suites, won’t have any type of kitchen or even a microwave. You can continue to save money on your vacation if you take advantage of the kitchen and the grills usually made available in vacation homes.
  4. A pool of your own! If you’re in a vacation home usually frequented in the summer, chances are it has a pool that you can use all to yourself.
  5. Plenty of communal space. If you want to play board games or yard games, it’s pretty much impossible in a hotel. With your own vacation home, you have living rooms and other communal spaces you can take advantage of.
  6. Parking aplenty. If you go to a hotel in a resort area, usually you can park one or two cars a room in the hotel parking lot. With a vacation home, no one is monitoring so you can pack in as many as you want.
  7. Free Wi-Fi. The last home we stayed in had free Wi-fi, which was a great perk. While paying $9 a day at a hotel isn’t horrible, I don’t plan on being tethered to a computer so $9 to check my email is a bit much (I know there are lots of hotels with free Wi-Fi, but many still charge!).
  8. More likely to be pet friendly. A vacation home is more likely to be pet-friendly, which means you can save on kennelling costs. Hotels? Forget about it, you have no chance.

It is not without negatives though. First, you’ll usually have to rent the vacation home or condo for an entire week, even if you’re only staying for a long weekend. My recommendation is that you split the cost evenly across the number of people, rather than the number of days people are staying.

Second, you’ll need a lot of people to fill the beds in a house to make it worthwhile. When we went to the Outer Banks, there were close to fifteen beds. We had enough people and the cost of the home was ridiculously cheap, but if you don’t know enough people then it may not be worth it.

Despite the two negatives, which are potential deal-breakers, renting a vacation home beats a hotel in my book.

Phew, I need a vacation after that!

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The Editorial Team at Healthcare Business Today is made up of skilled healthcare writers and experts, led by our managing editor, Daniel Casciato, who has over 25 years of experience in healthcare writing. Since 1998, we have produced compelling and informative content for numerous publications, establishing ourselves as a trusted resource for health and wellness information. We offer readers access to fresh health, medicine, science, and technology developments and the latest in patient news, emphasizing how these developments affect our lives.