It’s been said that some people spend more time planning their vacations than thinking about how they will save for retirement. It shouldn’t be that way.
A decent amount of forethought can lead to better savings and loads of fun — not to mention less stress.
Whether you’re an obsessive planner or just looking for a pre-fab itinerary, we’ve got you covered. We’ve rounded up the best travel booking sites to help you to figure out where you want to go, what you should do while you’re there, and how to save money on every detail of your trip.
Because you don’t need a stash of airline miles and hotel points to travel on the cheap (though it’s an enormous help).
Best booking sites for flights & transportation
There are dozens (hundreds?) of sites that sell airfare. The prices are pretty consistent, and most sites are pretty forgettable. However, there are a few that stand out.
Read more: When is the best time to book a flight?
Google Flights is the most comprehensive tool in existence for booking impossibly cheap airfare. It’s super handy for finding inexpensive routes between your origin and destination, and it’s even helpful for award flights (but that’s a whole other post).
Google Flights pairs unique search filters with super visual search results that make it easy to find good deals almost instantly.
For starters, you can enter up to five origin airports and five destination airports. You can also view dates two months at a time.
Those who are flexible with routes and dates will most easily find the bargains. If you’re willing to drive to airports other than the one nearest to your home (and nearest to your vacation spot), this can be a huge money-saver. For example, if you live in Cleveland and you want to visit Venice, you could enter Cleveland, Chicago, Detroit, and Columbus as your origin — and Venice, Milan, Rome, Florence, and Naples as your destination. You’re guaranteed to find a steal. I’m currently seeing several of those routes for under $400 round-trip in economy.
Google Flights also lets you not enter a destination. If you just leave the “Where to?” search box empty, you’ll see an interactive map after clicking the search button.
As you can see, Google offers lots of search parameters, such as price, number of stops, airline alliances, flight duration, and more. I like to leave my destination blank and then lower the price filter to under $500. It’s fun to see how far you can go for peanuts.
Read more: How to find a cheap airline ticket
Similar to Google Flights, SkyScanner allows you to leave your destination box blank and search “Everywhere.” But it’s got a few things Google doesn’t.
First, it’s got a button that says, “Cheapest month,” giving you the ability to immediately view the cheapest flights available to every conceivable destination.
Second, it’s got a very user-friendly list — in ascending order — of the cheapest destinations. You’ll see it after clicking the “Search flights” button. Scan the list until you find the country you’d like to visit. Once you click on it, you can then select the specific airport you want to fly into.
Below is a calendar of flights to Germany using the “cheapest month” feature. As you can see, round-trip economy prices from JFK appear at just above $300. That’s… incredible. In some situations, it could even be worth flying to New York to catch this cheap flight if you’re not nearby.
Momondo has a few similar features to SkyScanner and Google Flights. But there is one spectacular thing about Momondo. Of all the sites I’ve used to book flights (and I’ve used a ton), Momondo most often gets prices wrong — in a good way. These are called mistake fares, and they can be hundreds or thousands of dollars cheaper than the intended price of a flight.
For example, I once booked a round-trip economy flight between Washington, DC, and South Africa for under $350 on Momondo.
Momondo also allows you to keep the destination blank and search all over the world at once. You can search in monthly increments, and the site will instantly refresh its list of cheapest destinations under the interactive map. It’ll also tell you which specific dates you’ll need to book to get those super cheap fares.
Best booking sites for accommodations
Again, there are tons of sites dedicated to helping you find hotels. Most of them will get the job done, but we’ve picked sites that have something special about them.
Airbnb allows you to rent houses, apartments, villas, cabins, and even single rooms owned by other people. I’ve used it more times than I can count, and I’ve never had a bad experience.
Airbnb is superior to hotels in a few ways:
- Airbnb has more than 7 million listings. It’s estimated that there are just 187,000 hotels worldwide.
- You can often get double or triple the amount of living space as a hotel room for cheaper than you’d pay at a hotel.
- There are plenty of unique properties at which you can stay that you will never find at a hotel. I once stayed in a massive treehouse in Barbados and to date it’s still one of my favorite trips.
You can find Airbnb locations in tons of places where hotels don’t exist for hundreds of miles. It’s a great option for anyone whose travel takes them off the beaten path. If you want a bit of Alaskan wildlife, you’re sure to find a yurt available in the middle of nowhere.
Airbnb is also ideal for families or anyone booking an extended stay. You’ll almost certainly have a full kitchen, washer and dryer, and other amenities of home that hotel rooms usually omit. Plus, when you book in weekly or monthly increments, some hosts give a BIG discount — even 50% or more.
Check out the below discount for a month’s stay at a quaint cottage in Ireland. That’s a 73% discount. In other words, it’s cheaper to rent 30 days than it is to rent eight days! That’s wild.
However, there are a few downsides to Airbnb that are worth noting and which might compel you to choose a hotel instead:
- Airbnb doesn’t have a loyalty program. You can’t earn and redeem points for stays in the same way that you can with a hotel — and there are no elite status benefits.
- There isn’t any real quality control. You can read reviews from other travelers, but depending on the location you book, you may find its standards below your expectations. Alternately, most hotels are kept to a certain standard. I’ve never booked a Hyatt hotel that I thought was remotely unkept.
Read more: Hotels vs. Airbnb: How much can you save?
Google Hotels is another great tool that works similarly to Google Flights. Its most straightforward use is to enter the city or location in which you’re looking for a hotel, and Google will give you a digestible map of the area with prices.
But Google comes in again with some hard-hitting filters, including:
- Hotel class
- Property type (hostels, B&Bs, beach hotels, apartments, etc.)
- Hotel brands (Hyatt, Marriott, Hilton, IHG, etc.)
Best of all, you can zoom out of whichever location you searched to find hotel prices worldwide. This is a great tool for planning your vacation — especially when you pair it with the price filter. You can find some mega-cheap four- and five-star hotels in all sorts of fun locations.
Below is a search for Europe hotels under $42 per night. The closer you zoom in, the more results you get.
Google is also excellent at finding less publicized hotels. Most locations on the map have a bubble containing the nightly rate. But if you look closely, there are many more hotels.
Here’s a look at rural northern Thailand. When we zoom in, we can see small dots sprinkled around the map. These are hotels that you often can’t book online (though sometimes you can). You can simply roll over the dots with your mouse to see what they are, as I’ve done with the Royal Inn Hotel.
Roomer Travel is too fun not to mention. If you’re flexible with dates and destinations, you could have the vacation of a lifetime for pennies on the dollar.
Roomer Travel is a place where people can sell their hotel reservations. This often comes in handy when someone has purchased nonrefundable travel and can no longer take their trip — they’d prefer to sell it to someone else, even for a fraction of the price.
Of course, this means you’re hostage to both the dates and the room type of the original booking. But you can filter your search by hotel class, TripAdvisor rating, and free amenities. You can also sort your results by the size of the discount, which is your best strategy if you’re simply looking for some crazy deals that are worth booking airfare to take advantage of.
You’ll notice the discount percentage at the top of each listing. The highest discount at the moment is 85%.
Roomer might sound a bit sketchy, but it’s not. It serves as a secure middleperson between you and whoever is selling the reservation.
Best booking sites for travel packages
For the most part, I’m violently opposed to travel packages. Occasionally you’ll find a good value, but if you’ve got the patience, you can almost always piece together a cheaper vacation by yourself.
One exception is Costco Travel. Occasionally, Costco Travel will drop a travel package promotion so generous I can hardly believe it. The last Costco Travel package I booked included the following for just north of $1,800:
- Five nights in an ocean view suite at the ridiculously expensive Ritz-Carlton Kapalua in Maui
- $150 per day in resort credits
- Resort fee waived
- Free car rental
- Free daily breakfast for two
Had I booked this trip outside of Costco Travel, I’d have spent more than $6,000 for the same experience.
Costco Travel packages can be legit, particularly if they’re having a promotion. Still, I wouldn’t recommend booking them with regularity. With some points and miles know-how, you could book a nearly free vacation that’s much more fun than what any travel package will offer you.
Read more: How to choose a travel rewards program
Best booking sites for activities
Full disclosure, I’ve never booked Airbnb Experiences. But it appears to be one of the best and most authentic “experience” services around. Locals essentially list their expertise online for anyone interested.
Want to know where the best beer is in Philadelphia? There’s a local who’s willing to take you around. Want a buddy to kayak with on one of the Great Lakes? Book someone to take along. Always dreamed of walking through a herd of sheep in the hills of Ireland? There’s someone who would be glad to give you that experience.
All this to say, not all Airbnb Experiences are offered by people whose full-time job is to entertain. But you can find activities to do that the locals would be doing for fun, anyway.
Chase Ultimate Rewards® Activities
The Chase Travel Portal gets a mention because you can use Chase Ultimate Rewards® points to book your experiences. You’ll get a rate of 1.25 cents per point if you’ve got either the Chase Sapphire Preferred® Card or Ink Business Preferred® Credit Card, and 1.5 cents per point if you’ve got the Chase Sapphire Reserve® Card.
To use the Chase Travel Portal for experiences, navigate to the “Travel” section and then find “Activities” near the top of the page. You’ll have to enter which city you’ll be in, and the dates you’ll be there. Chase will then find all the events happening during your stay.
Marriott Bonvoy Moments
Marriott Bonvoy Moments is one of the more standout options for booking activities for one simple reason — many of its options you can’t purchase otherwise. Yes, you’ve got options like concerts and sports events, but you’ll also see things like:
- Throw out the first pitch at an MLB game
- Meet a famous chef and attend an intimate dinner prepared by them
- Walk the red carpet before an awards ceremony
Here are a few examples of Marriott Bonvoy Moments. Some are auctioned off, and some are “buy it now.”
Marriott Bonvoy Moments may be worth building a vacation around. Instead of using it to look for things to do while on your trip, it can be a reason for booking the trip in the first place!
Viator is a juggernaut of activities and experiences during your travels. There is nothing wrong with it — no matter what you want to do, there’s probably an option on Viator — but in my experience, personal touch is not what these folks are about. Any time I’ve booked it, I’ve felt more like livestock being processed as quickly as possible so that the tour group after me could begin.
Viator activities are customer rated, which should keep hosts honest for the most part. I’ve never had a bad experience with them, per se, it’s just felt very businesslike. They have undeniably fun things to do, though. Just enter your location to see all the activities near you. You can filter by duration, genre, and even if it’s good for kids or for avoiding crowds.
The best vacation booking sites nowadays can do much more than just book your ticket or hotel room. With the internet as your travel agent, DIY vacation planning can even be enjoyable and stress-free.
Featured image: Patiwat Sariya/Shutterstock.com