The Best Times of Year to Go on Vacation

The best time of year to go on vacation is any time, really. No matter when your trip is planned, we’re sure you’ll be more than happy to take a week off and relax. Then again, when reality hits, there are so many factors to picking the perfect time for your trip: work schedules, school schedules, weather, and price—all influencing your final decision.

It’s useful to consider the off-season for the destinations you’re thinking about visiting. The off-season is the off-season for a reason. It might mean the days are short and cold, tourist attractions may be closed, or the nature and sports in the area might not be as available. But it could be worth the trade-off. You may get far better deals and experience fewer crowds. Even better, there is often there is a brief time called the shoulder season in between the off- and peak-seasons. Shoulder seasons have fewer travelers and slightly lower prices than peak-seasons but with fewer trade-offs than off-seasons. This is often the best time for your vacation, and it’s different for every location.

So you can be strategic with this year’s vacation time, we’ve rounded up the best places to travel in every season. Whether your primary consideration is price, weather, how many other travelers will be there, or major holidays and events, we’ve mapped out the best time of year to travel to different spots in the United States.

Best Time of Year to Go on Vacation_lake tahoe in spring

The Best Trips to Take in Spring

Spring is when we all start to get the travel itch after a long winter of being cooped up, but it’s also the season that requires the most strategic travel. The last thing you want is to plan a trip to Chicago expecting to be surrounded by tulips, only to be met with an April snowstorm. National parks and winter sports are a great choice for early spring, and you can often get good deals on spring break destinations if you wait until later in the season.

Get into Nature

Early spring is the best time to visit national parks like the Grand Canyon. Cooler temperatures will stave off crowds, and you’ll get shoulder season prices. The Residence Inn Flagstaff is the perfect place to start the road trip out west you always promised yourself you’d take.

If You’re Not Ready for Winter to End

Lake Tahoe in April is the spot for you. Visit Hotel Beckett and enjoy one last trip down the mountain before it’s time to pack away your gear for the summer.

Best Time of Year to Go on Vacation_key west beach

The Best Trips to Take in Summer

Summer is when travel gets the most expensive. Between school vacation, events like weddings, and more flexible work schedules, most people are traveling during this time. If you want to save money and avoid other tourists, it might be a good idea to wait for the fall. But if your schedule commits you to a summer vacation, here are some of your best options.

Off the Beaten Path

Summer is the off-season in South Florida. It’s hotter so there are fewer tourists, and you’re more likely to find deals on resorts, private beaches, and other travel costs. Summer could be the perfect time for you to plan a trip to Key West, Fort Lauderdale, or Miami. The hotel Casa Marina Key West, the EAST Miami, or The Dalmar Fort Lauderdale will provide the perfect escape.

Come on in, the Weather’s Fine

You can’t beat a trip to Maine or the Pacific Northwest in the summertime. Between the perfectly warm but non-sweaty weather, the beautiful coasts, and the quaint little towns, you’ll be in heaven. We like The Press Hotel in Portland, Maine, and The Hoxton in Portland, Oregon, for all your lobster and rose garden dreams, respectively.

Best Time of Year to Go on Vacation_los angeles in fall

The Best Trips to Take in Fall

Fall is possibly the best time of the year to travel. You’re past peak summer travel, so prices have dropped off, and you have some of the best weather of the year. Early fall, like September, won’t get you a glimpse of foliage, but you won’t have to fight the crowds either. Fall is a great time to visit theme parks, explore new cities, or get discounts on summer sports like scuba diving or windsurfing.

Save a Buck

You’ll save so much money booking your trip to Los Angeles in September instead of July or August. Use those savings to splurge on an awesome hotel. How about the Huntley on Santa Monica Beach, or maybe the Ritz-Carlton Los Angeles? The early fall also brings dramatic decreases in price at resorts and tropical locales. It might just be worth planning a fall wedding so you can take advantage of deals at resorts like the West Bay Club in the Turks and Caicos Islands.

Visit the Happiest Place on Earth

September is also the best time to visit theme parks, as school starts back up and the crowds die down. If you can fit it into your schedule, Disney World is the perfect place to visit in the fall. We recommend staying at the Walt Disney World Dolphin.

Best Time of Year to Go on Vacation_jackson hole in winter

The Best Trips to Take in Winter

Winter is a great time to travel because prices are low and crowds are sparse. As long as you’re not traveling around the major holidays, you’ll be sure to score a good deal. Colder temperatures and shorter days mean this isn’t a great time to explore a new city, but you couldn’t pick a better time to visit a resort, try your hand at winter sports, or maybe visit the tropics.

An Island in February? Yes, Please.

Prices in Hawaii dip in the winter, especially around February. We literally can’t imagine anything more perfect than escaping dark, cold winter in February. As you get started planning February 2020 in Honolulu, we recommend The Grand Islander.

If You’re a Ski Buff

Jackson Hole, Wyoming, is the perfect place for you. The Inn at Jackson Hole is an ideal winter getaway: you’ll be close to the slopes, the granite hot springs, and the National Elk Reserve. We can’t think of a better place to enjoy all that winter has to offer or stay cozied up with a book next to a fire.

No matter where the wind takes you, we’re here to help you search hotels all year round. Visit to start searching for hotels in a way that puts your best interests first and is easy to understand. When you’ve found the hotel for you, we’ll transfer you directly to the hotel’s website to secure your room, rate, and loyalty points too. That’s how we make travel work for you.