4 Reasons Why You Should Book Your Winter Vacation Now

you should plan your winter vacation now
IN THIS ARTICLE

With summer still in full swing, your winter vacation may not be at the top of your mind. However, waiting until the last minute to book your winter vacation could cost you. We have 4 reasons why you should book your winter vacation now instead of later.

you should book your winter vacation now

1. Airfare Costs

Everyone should know that airfare is cheaper when you book in advance. However, not too far in advance. Airlines release their schedules typically about 9 -12  months out, but sometimes the sweet spot to book the best priced flights is somewhere around 4-6 months from your departure date. The closer you get to the date of your vacation, the less likely you’ll be able to find the pricing you desire, or the seats you want on the flights you’d prefer.

hotel special

2. Hotel Specials

Hotels oftentimes offer better rates for early bookings. Many hotels offer discounts for guests who book 60 days or more in advance. Booking in advance is also advantageous for securing specials from hotel partnerships with other local companies. For some of the resorts you may want to book, they often have limited bookings that include special add ons at a discount or for free. These add ons are things such as golf, scuba diving, fishing trips, and more that you will miss out on if you wait to book. 

bungalow

3. More Availability

You’ll have more vacation choices. The closer it gets to winter, the more likely popular vacation spots will fill up. This is especially true for Hawaii. By booking now, you’ll have a better selection of vacation destinations as well as hotels and room types to choose from.  Having more availability to choose from is also very important for those who might have a tighter budget to work with. With more availability, the better the pricing is going to be for you.

Planning early is also super important if you’re going to have a larger group of people. If you need a 2 or a 3 bedroom condo, these options are limited and they fill up fast. If you are needing accommodations like that, or a room block for several couples, you should book your winter vacation now.

anticipation

4. Anticipation

You’ll have something to look forward to. Winter can be a long and dreary season for many of us. The fall is chilly and crisp, and for those of us in Oregon, the winter tends to be gloomy, cold, and wet. Thanksgiving and the winter holidays can be an enchanting time to spend with family, but also exhausting. Which is why you may need a winter getaway to recharge from it all. 

If you have a sunny vacation to look forward to in mid January or February, it can make the winter months much more bearable and not seem so long. Go ahead and book that winter getaway now – you’ll be glad you did! 

Travel Agent

Are You Ready to Book Your Winter Vacation Now?

It might be hard to think about winter plans right now, even if the weather has been weird this year. But soon enough, the leaves will turn and the cold will come again. Call Wanderland Escapes today to discuss your winter destination desires. Whether you want to go somewhere with warm water and fruity drinks, or maybe you’re more into a place with snow covered mountains and skiing. No matter what you prefer, we can help you get there! 

Rebecca with Wanderland Escapes has personal experience with many beautiful destinations, that are great for winter travel.  She also travels to many of these destinations regularly to keep ahead of the curve for new events, restrictions, and specials to share with her clients. Her expertise is unmatched.

 

Ready to elevate your travel?​​

Skip the hours of research and the stress of uncertainty. Let's design a trip that matches your budget and exceeds your expectations.​

SHARE:

Latest Blogs

January 8, 2026
Scroll to Top

Trip Design Profile

Tell us about yourself to get started.

Step 1 of 5

Who is planning this journey?

Traveler

I am planning a trip for myself, my family, or my friends.

Travel Advisor

I am a travel agent researching resources or planning for a client.

Where is your compass pointing?

🌺

Hawaii &
Polynesia

🏝️

Caribbean &
Mexico

🏰

Europe

🦅

USA Luxury

🚢

Global Cruises

Surprise Me

Who is embarking on this journey?

Solo

Couple

Family (3-5)

Group (6+)

How long will you be escaping?

7

Days

(1 Week)

10

Days

14

Days

(2 Weeks)

21+

Days

(3+ Weeks)

What is your preferred style of travel?

Standard Luxury

4-Star boutique hotels, curated local experiences, comfortable transfers.

Premium Luxury

5-Star resorts, private transfers, exclusive access & unique experiences.

Ultra Luxe

Private villas, helicopter transfers, dedicated white-glove concierge service.

Profile Complete

Based on your selections, here is your customized plan.

Estimated Starting Budget

$0

*Excludes international airfare. Estimate based on your selected travelers, duration, and luxury tier. Professional planning fees apply.

Submit Trip Request Form

We will review your profile and reach out within 24 hours.

Calculator Maintained by Muon

The Luxury List

Unlock our curated guide: "5 Hidden Gems in Polynesia" plus monthly inspiration for the discerning traveler.

Where should we send your guide?

Contact Rebecca

Let's have a chat about Travel!