Home > Travel > How to Afford a Vacation- Time Off and A Place To Stay

How to Afford a Vacation- Time Off and A Place To Stay

Coastal view from our summer vacation

Coastal view from our summer vacation

When you work full time, especially if you own a business, it might be hard to take a vacation. If you are in debt or living paycheck to paycheck, that makes it even harder. We recently took our longest vacation in over a decade. While a ten day vacation may not seem like long to world travelers, if you knew my work history, it’s nothing short of a miracle. If you are dreaming of sandy beaches and mai tais, but don’t feel like you have the time or can afford to take a vacation, maybe there is a way.

Work is Ruining all My Fun!

I think the biggest obstacle facing most would be vacationers is work. If you work for someone else, it’s hard to take extended time off. Even if you are the boss, it can be tough. You could find yourself ten years into a job and only taking a few consecutive days off here and there.

To be able to take time off, you have to make sure there is someone you can delegate your work load to, and you have to be able to have enough money to supplement your income if you are taking unpaid leave. There are tons of ways to earn more money or cut expenses you don’t need, like satellite TV. If you have to put a trip on credit because you don’t have money on hand to cover it, then don’t go.

Where Do I Stay?

Paying for hotel costs can certainly limit your vacation budget. Likewise, staying somewhere dirty or unsafe to save a few bucks can really dampen the traveling spirit as well. Luckily, there are several low cost ways to find accommodations while on vacation.

  • Use Credit Card Reward Points– This has become my personal favorite. It takes good credit, discipline, and knowing your limits, but if you do it right, you can get all kinds of free stays in some great hotels. 
  • Use AirBnB or VRBO. Pauline has much more experience with AirBnB, which would be a great option for single travelers or couples. Since we have a child, we don’t want to stay in a house with people we don’t know. For this recent trip, we rented a cottage on the Oregon coast for much less than the crappy shoreline motels in the area.The other benefit is laundry and a full kitchen, which saves tons on food expenses. Yes, you could get taken, but if there are enough reviews, you should be fine.
  • Swap Houses– I haven’t tried this one, but I would certainly consider it if we found the right family and location. Basically, you trade houses with someone in an area you want to visit with someone who wants to visit your area. It might be tough if you live on Skid Row, but if you live in a decent neighborhood close to attractions people come to see, why not?
  • Traveling Caretakers– You can actually stay for free in many places if you don’t mind taking care of someone’s property while they are away. Again, I’ve never tried it, but it might not be a bad way to see the world.
  • Camping- Camping might not be the luxury you are looking for, but it does provide a cheap and often relaxing way to travel. Some of our best trips have been had based out of campgrounds.

I guess you could also stay with family or friends, but family trips are often not really vacations. If you do need a vacation, finding how to take time off and securing a place to stay are two really big parts of the puzzle. Luckily, there are ways to make it happen if you want it bad enough.

What is the best place you have ever stayed on vacation and was it cheap or expensive?

About Kim Parr

Kim Parr is a private practice optometrist, freelance writer, and personal financial blogger. You can follow her journey to 20/20 financial vision at Eyes on the Dollar.


  1. The best place I’ve ever stayed on vacation was definitely a Sandals resort in Jamaica for my honeymoon. It wasn’t cheap, I can tell you that! Going to an all-inclusive was awesome, though, because we could eat and drink as much as we wanted and didn’t have to worry about additional expenses.

    • We did all inclusive for our honeymoon as well. I think I ate more that week than I ever have in my life. Nachos at 2AM? Why not?

  2. The best place we ever stayed is a toss-up between our honeymoon and the cruise we took for our 10th anniversary two years ago. The honeymoon was a blast because we stayed in B&B’s in Ireland, but having a suite on a cruise is pretty nice as well. 🙂

  3. The best place I’ve ever stayed was in a tree-house in Costa Rica for our honeymoon. That was definitely not cheap. If you’re trying to save money, I just think it helps to be open-minded and creative. There’s almost always a default option for whatever area you’re traveling to, but that default likely isn’t the most cost-effective. Thinking a little creatively can help you understand what your options really are.

  4. The best place I ever stayed on vacation was my brother in laws house believe it or not. I had never been to Oregon and, my fiance wanted to go. The good news is, her brother lived there and, we had a free stay as long as we wanted. The vacation was so great that we moved from Florida in a month to come back to this place. I absolutely love it. Now, the amenities weren’t exactly at the bro’s house…I mean, there was no continental breakfast but, it really was the best vacation ever!

    • After visiting Oregon this summer, I can certainly see the appeal. I’m just not sure if I could handle the rain.

      • You know, after living in Florida, I got all the sun I could handle I guess. The rain doesn’t really bother me because it’s the rains fault that I can look around and see such beautiful wilderness when I go up to Mt. Hood. It does definitely rain a lot though. Hey, would you mind stopping by my blog and joining the conversation? I just made some really big changes and, I’d love to know your thoughts. All the changes I made are in the most recent post!

        • You must have been sending me psychic signals. I just finished reading about your new design. Best of luck. It seems like a wonderful idea.

  5. One of the best places I stayed was in a large house (I shared a room with another single female traveler) when I went to the Big Island last year and found the deal through living social. Thankfully we had a great group of people (12 in all) and we had a cook the entire time and she made all our meals and packed our lunches when we went exploring. It was awesome not to have to think about that kind of stuff because it was all inclusive. I’m still considering doing some kind of house sitting gig when I travel overseas. Not sure where to start though so I need to look into that more.

    • I am really interested in housesitting at some point, especially if the whole Airstream idea falls apart. I know lots of people who do or have done caretaking in Telluride. They get an amazing place to live and have to hustle and be inconvenienced maybe for two weeks out of the year. Doesn’t sound so bad.

  6. I have never taken a long or extravagant vacation. I am going to make it a mission of mine to do next year though. After I save my emergency fund I want to start a vacation fund. I also want to look for great deals throughout the year. I have seen many cheap and desirable hotels on livingsocial.

    • I have no doubt you will hit that goal as well. One great thing about having small kids is that they like to go anywhere and you can make anything an adventure.

  7. One of my favorite vacations is staying at my father’s remote cabin with my extended family. There is no TV, no cell phone reception – just all of us together, hanging out. And I love it. On the other hand, I also really enjoy being pampered. 🙂 For pure relaxation, I’d say Turks and Caicos. We stayed an inclusive resort so we got treated like royalty. Spendy but worth it, until Taylor got an ear infection and couldn’t fly so we had to stay another two days. Because, you know, it’s horrible lounging around with people waiting to get you a fruity drink. 🙂

    • Shannon, I am the same way. I like to take camping and hiking trips where you get really dirty but feel like you earned you s’mores. I also like nice hotel rooms with jacuzzi tubs just as much.

  8. You know we be rockin’ them CC points! HOLLA!

    We are using VBRO for a family vacation with Mom and brothers and sisters though. Less than $2k for 10 days, full sized condo on the beach. Flights and car rental will be on points, though 🙂

    • If you have a group, the house is almost always the best option. It even worked out that way for our family of 3 for part of our vacation. The house was cheaper and much nicer than any of the hotels in that area.

  9. I can’t recommend camping enough. There are lots of great state campgrounds across this nation, many with cleaner bathrooms than cheap motels and you can often get a site with electric hookup so you can play some tunes while sitting by the fire. 🙂

    • I totally agree. Many of the KOA’s are almost like motels, but much cleaner and not smelly. Plus, you get to play with fire, and who doesn’t really want a legit excuse to build a fire?

  10. Thank you for the mention! You can rent full properties on Airbnb as well, Wimdu is another similar site. For less than 3 nights it is a bit of a hassle coordinating with the owner to get the keys, etc. Looks like I am off to a 2 months holiday next week haha it just came out of the blue, the more you take the more you want!

  11. My wife and I joined friends to visit the UK (England & Scotland ) by car nearly 30 years ago. By far, it was my favorite trip. We stayed in hotels, manor houses and a B & B. The B & B was one of my favorite although at the time, it was the cheapest ($20 per night for 2 people including breakfast)stay.

    • I have never done a B&B but should put in on my list if Jim and I ever get to take a trip alone. Not sure a small, loud child would go over well there.

  12. While many AirBnB places are single rooms, they aren’t all that way. I rented a full cottage on AirBnB for a family of four. It was a fine option for us and gave us an awesome place to stay.

  13. Thanks for the tips, it’s all about thinking outside the box! My biggest barrier is carving out some money for a vacation. I haven’t been off the continent in over ten years. Very depressing. Financially, things should start to shift soon!

    • A trip is a nice reward for reaching a financial goal. I don’t think it needs to be expensive, just something to give yourself a break for a job well done.

  14. I love all vacations- cheap or expensive. Some of my favorites are when we rent a condo in Florida and just play in the pool and ocean all week. It’s cheap and fun!

  15. I have been there with owning a company and never taking days off. Mostly because I did a horrible job hiring and didnt have anyone who could manage while I was gone for a few days. Being the boss is not as easy as everyone would like to imagine. That being sad the best places we have stayed have been at a all inclusive resort in Mexico(great place and time there) not cheap though. And we had a get little weekend getaway about 30 minutes from our home. Nice small boutique hotel and the wifey had a great time.

  16. I’ve been to so many places it’s hard to pick just one. I did like Thailand quite a bit. I am a planner so I make sure we save the cash first, I do research online and save as much as I can. I need a vacation now come to think of it lol. I’ll be going home soon.

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