How to Book an Amazing Cheap Vacation Package

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Sometimes planning a vacation is as fun as taking the vacation. But sometimes you want someone else to do all the work for you and just book a vacation package. Because, let's face it, sorting through hotels, itineraries, and flights can be a daunting task when you just want to get away. Plus, you can often find better deals when you book a package. (See also: The 5 Best Travel Reward Credit Cards)

Personally, I've booked multiple cheap vacation packages over the years. One time, I went to Toronto, Canada for a last-minute long weekend where we stayed in a 3-star hotel and got a nonstop, round-trip plane ticket for $300 — less than the cost of any multi-stop ticket without the hotel.

Another time, I traveled to Vienna, Austria for a week by booking a cheap vacation package — we stayed in a fancy 4-star hotel (they had a bowl of free mini-Toblerone chocolates in the lobby!) and got flights on a stellar foreign airline for about $500.

Perhaps the best deal of all the vacation packages I've purchased was a round-trip ticket to Hurghada, Egypt (a resort town on the red sea) plus a week in a 3-star resort, with two meals a day for $330.

How did I do this? Here are my cardinal rules for how to book a cheap vacation package, followed by an easy three-step process.

Tips for Booking a Cheap Vacation Package

For the greatest savings on your vacation package, use these nine tips to guide you through the booking process.

1. Be Flexible on Place

You're going to get the cheapest vacation package if you are completely open to any destination. I recommend either choosing an activity that you're looking for (e.g., beach, skiing, museums) or a general destination (e.g., Europe or South America) and then looking for vacation packages that meet this more general criteria. When you're more flexible on place, you're going to get a better deal. (See also: Affordable International Vacation Destinations)

2. Plan Far in Advance or Book Last Minute

The best vacation deals I've found have always been last-minute trips. However, my trip to Vienna was planned about nine months in advance. You are best off planning more than three months in advance (four for summer travel) or less than two weeks. Planning a trip in only two weeks may sound scary — but you can block off the dates now and choose the destination later!

3. Be Flexible on Time

Just like with flexibility on destination, travelers who are flexible with when they go are going to get better deals. "Time" includes days that you travel, how long you stay, and even time of day for flights. The more flexibility you have, the cheaper vacation package you'll snag. (If you're unsure of how to search based on flexibility, start by checking out my favorite search engines for flexible travel.)

4. Be Flexible on Amenities

Most vacation packages typically include flights and hotel. Some also include a rental car, admission passes to a nearby attraction, or all-inclusive meals. It's best to be flexible on the amenities you want — you can always opt to not use the tickets or to find a rental car on your own.

5. Bring a Friend (or Two)

The majority of vacation packages are priced per person for two people. If you are traveling by yourself, you'll likely see a surcharge. Some packages charge less per person when there are three or four people all booking together (usually sharing one room).

6. Know That You Can Extend Your Dates

A vacation package frequently has certain dates or number of days set in stone. For example, a long weekend package might begin on a Friday and go until Monday. Don't feel confined by these dates — many of the vacation packages will allow you to extend the dates for several more dollars. And if they won't let you extend your trip, consider finding your own way home. One time, for example, a vacation package I found was such a good deal that I booked it, but I wasn't able to extend the trip through the company. So once at my destination I found different lodging for the duration of the trip and bought a one-way ticket home. (See also: Hotels vs. Hostels)

7. Travel From a Major Airport Hub

The best vacation packages are priced from major airport hubs like LA, NYC, DC, and Chicago. Some companies will only let you book from these hubs. Other companies will add a surcharge for smaller airports. If you're getting a surcharge added for your airport, consider booking this flight separately by checking to see if you could get a better price on your own. Just be forewarned that if something goes wrong with your first flight to the hub, you may be left in a lurch. So plan to arrive extra early or buy travel insurance.

8. Travel From a Foreign Country

The $330 steal to Egypt that I snagged? That was flying round-trip from Moscow. (Hurghada happens to be a hotspot for Russians.) When I traveled in Germany I noticed some amazing prices on vacation packages to foreign countries. So, if you're lucky enough to have the flexibility to spend more time traveling — once you get to your first foreign destination, head to a travel agency and ask where the best vacation packages are to determine your next stop.

9. Splurge: Spend the Money to Upgrade

Usually with vacation packages, you'll have a cheaper option for the package, then you'll be given an option to upgrade to a fancier hotel. If you upgrade, you'll get a much better hotel in a much better location. Every time I've upgraded, it's been more than worth the cost (e.g. the Toblerone hotel in Vienna). And every time I've passed I've regretted it. (The Egypt hotel had a barely functioning shower. For $50 more we could have stayed at a 5-star resort with swimming pools with swim-up bars. But at the time we had little money and didn't see the value of the better hotel — until we arrived.) (See also: How to Negotiate Your Hotel Deal)

How to Find a Cheap Vacation Package in Three Steps

Now that you know the tips, you're ready to start actually searching for a vacation package.

1. Make Some Decisions

First, look through the tips above and make some decisions about dates, places, people, budget, etc. As I mentioned, the more flexible you are the cheaper vacation package you'll get; but note that you'll also spend more time searching for packages.

2. Determine What's a Good Deal

Before you know that you're getting a cheap vacation package, you need to get a baseline price to compare the vacation package to. I recommend choosing you favorite travel search engine (I like Kayak) and entering a flexible date search for your city to the location you're considering and first get a baseline sense of what airline tickets cost. Next, use the search engine's hotel function and see the approximate cost of a hotel for a stay of your length. For instance, if the cheapest fares you are finding are $500, and the hotel for a week's stay is $600, you'll know that a vacation package that's less than $1100 is a good deal.

3. Search and Book

How to you actually search for a deal? Here are the best places to look:

For Last-Minute Trips

• Lastminute.com (I've used Lastminute.com and liked it)
• Hotwire
• Priceline

For Flexible Locations

• Go-today has the easiest browsing and good deals for travel abroad. (I've used Go-today for several trips that have been outstanding.)
   
• Priceline allows you to be flexible on location — just look under the "theme vacation ideas" box. (Here's a good post with general Priceline Bidding Tips that will help you further understand the Priceline process.)
   
• CheapTickets similarly has packages based on theme and destination.

For All Packages

• Pick up the travel section of your local paper — as some of the best deals on packages from your local airport will be listed in your local paper with a local travel agent.
   
• Try Groupon Getaways. Groupon for travel is new, and I haven't tried it, but based on what I've seen there are some great deals through a partnership with Expedia.
   
• Finally, the traditional online travel agencies Orbitz, Expedia, and Travelocity all have good deals, though the sites are easier to navigate if you have a set location and dates.

Lastly, don't forget Wise Bread's awesome list of Travel Resources.

Have you ever booked a vacation package? What was your experience?

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