How to Plan Your Winter Break Getaway

Airplane on runway

We know how dreadful and gloomy winter weather can get, and we know that lots of people like you are looking to book vacations to get out of the cold and spend some time away. Today, we’ll give you some tips for how to plan your winter break getaway.


Just a heads-up that some of the services we’re reviewing here have affiliate partnerships with us, so we may earn a commission if you visit one of them and buy something. You can read more about how this works at

First, let’s go over some things you should know before you start the process of booking your vacation.

Before you start booking your vacation:

1. Figure out a specific location or type of destination you’re interested in traveling to.

Have a destination in mind before you start planning your vacation. Depending on where you’re looking to travel, you may need to do other things (such as getting the appropriate vaccinations, paperwork, etc.) before you leave.

2. Determine how many people will be traveling with you.

This is one of the most important things to determine before you begin looking to book online, as a website needs to know this information in order to search for vacancies at hotels, resorts, and so on. In addition, sometimes you can get discounts on vacation packages depending on how many people are traveling in your group. Some websites, resorts, hotels, etc. may offer discounts for people traveling in groups.

3. Have an idea of the amount you’re willing to spend on your vacation.

Figuring out your budget will help you to narrow down the possibilities once you start your search for vacation accommodations. Try to keep a firm number in mind when searching, because there are many websites you can search on, and one of them is bound to have something in your price range. It’s also always better to have an idea of how much what you’re looking for might generally cost, so you know if you’re getting a good deal or not.

4. Try to book as far in advance as you can.

Planning out and booking your vacation in advance will give you more time to figure out anything else you need to get done before you leave (pet-sitters, sightseeing tours, etc.) Prices for travel also fluctuate greatly over time, so it’s always better if you can track the prices for the trip you are interested over time, and then purchase at the optimal moment.

5. Don’t forget to purchase travel insurance.

Having travel insurance for you vacation is always a good idea. In case anything happens unexpectedly during your trip, having travel insurance will make sure you’re covered. Look into purchasing travel insurance when finalizing your trip.

You can purchase travel insurance online here.

Now that you have all of those things figured out, it’s time to start looking for options to book your vacation. Here’s a roundup of some of our favorite travel booking websites.

9 great sites for booking your winter vacation

1. Priceline


Priceline logo

Priceline is a unique travel booking website that offers some really awesome travel deals. If you’re looking to book a hotel room or car rental for your trip, you can check out Priceline’s “Name Your Own Price” feature to bid on travel accommodations. Priceline also offers great deals on flights! If you’re looking to save some money on booking your winter getaway, may be a place you can find the right deal for you!

To learn more about Priceline and how to use it, check out our free Priceline course.

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2. Expedia


Expedia logo

Expedia is a great travel booking website to check out, especially if you’re looking to book all your travel accommodations at once. Expedia offers great deals on travel packages that include your flight and hotel, car rental, etc. all in one, and they guarantee the lowest price on your vacation. They also have a rewards program that will get you coupons for a discount on future purchases.

If you’re interested in learning more about Expedia, head on over to our Expedia course.

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3. FlipKey


FlipKey logo

FlipKey is a cool travel booking site where you can rent out a space from property owners in thousands of different cities worldwide. This is a great option if you want to see what it’s like to live in the city you’re looking to visit, or if you want to save on your stay by renting an apartment or house rather than staying in a hotel. FlipKey has a verification system to ensure that you can trust the people you’re renting from – so you can feel safe renting a property on FlipKey.

FlipKey button

4. Orbitz


Orbitz logo

Orbitz is a popular travel booking website that is known for their great customer service. They offer great travel deals on flights, hotels, car rentals, cruises, and more! Orbitz also has a rewards system called “Orbucks” that you can use to earn points that will get you a discount the next time you purchase travel accommodations on Orbitz.

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( logo is a hotel booking website where you can find awesome deals on hotels for the destination you’re looking to travel to. Although it only offers deals on hotels, and not on other travel accommodations like flights or car rentals, it has a larger selection of hotels available than a lot of other travel booking sites – over 650,000 properties! Other great things about this company are that they don’t charge booking fees, have great customer service, and they usually offer free cancellation. button

6. HomeAway


HomeAway logo

HomeAway is similar to FlipKey, where you can rent properties in the area you’re looking to travel to. HomeAway offers travel insurance and renting guarantees through their site, so you’ll be safe booking your stay with them. They also don’t charge booking fees, so you won’t be spending extra money on your rental. HomeAway has over 1 million different rental property listings on their site – all over the world, so you’re sure to find a great place to stay during your winter getaway.

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7. Hotwire


Hotwire logo

Hotwire is another travel accomodations site that’s similar to Priceline. They offer really good prices on travel accommodations from travel companies that are looking to sell these accommodations so the rooms/seats don’t go unsold. You might not be able to see all the details before you book on Hotwire (like the specific hotel or airline) but you’ll know the area you’re staying in or where your flight is going, and you’ll get a really awesome discount.

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8. Trivago


Trivago logo

Trivago is a cool travel site where you can compare prices for the same hotel room on different websites. This way, you can ensure you’re getting the best price for the hotel you want. Trivago also shows reviews of hotels from people that have stayed there before, so you can get an idea of what a hotel will be like before you book your stay. Trivago can save you lots of time by showing you the prices for the same hotel on different travel sites, so you don’t have to do tons of research to find the best deal.

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9. Kayak


Kayak logo

Kayak is similar to Trivago – it lets users compare travel prices for flights, hotels, car rentals, and activities, so that they can find the best price. You can also use Kayak to track the changes in the price of travel accommodations for a certain destination over time to see if the prices are going up or down. Kayak also has features on their site that you can use to create your itinerary and help in the process of planning your vacation.

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Now that you’ve booked your essential travel accommodations, like flights and hotels, you might want to look into purchasing some activities for your vacation. Here are some useful websites where you can book tours or excursions, or make restaurant reservations to add to your winter vacation itinerary.

3 sites for booking fun activities for your vacation

1. TripAdvisor


TripAdvisor logo

TripAdvisor is a great site to read reviews and see photos of various hotels, restaurants, and other travel activities, but it also allows users to make reservations and bookings through the site as well. You can browse TripAdvisor reviews for good restaurants or tourist attractions in the place you’re traveling to, and then book whichever ones appeal to you – all on the same site! TripAdvisor is a great place to find the best activities and restaurants to visit on your vacation.

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( logo is a really cool website that helps users find fun things to do on vacation. They make it easy to find and book unique experiences for your trip, like excursions, tours, and day trips to see popular attractions. A team of travel experts at Peek pick the best activities from high quality vendors and providers, so you get the best experience. button



BookIt logo

BookIt offers great deals on travel activities and services in tons of different places you may be traveling to. Whether you’re looking to book a horseback riding adventure, swim with dolphins, or go on a safari tour, you can find a deal for it on BookIt. Each activity listed on their site has a full description with details of the activity, price, and approximately how long it takes. You can search for activities by destination, and filter results by price to find one that’s just right for you.

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That’s it for this article on how to plan your winter break getaway. We hope you found it helpful for planning your vacation!

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