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The Best Times to Book Home Rentals for Every Vacation of the Year

Get a head start by booking your vacations before prices—and demand—go up!

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Whether you’re dreaming of the mountains or beach, booking a vacation rental instead of a hotel room is an invitation to slow down and savor each destination. Vacation rental company Vrbo analyzed past reservations to pinpoint exactly when demand skyrockets for each vacation season—you’ll save time and money by booking your trips early. Here are the best dates to book your 2020 vacations by, including where to go for the most fun, relaxation, and family time during each holiday travel season. Before you book, you’ll want to know the vacation rental mistakes to avoid.

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By February 10: Book a spring break trip to Dahlonega, Georgia

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This north Georgia town is a charmer in springtime when the Appalachian Mountain town comes alive with music festivals, artisan markets, and winery tours. From the Dahlonega Literary Festival in March to the Bear on the Square Mountain Festival in April, families will find plenty of entertainment over Spring Break. Rent a home within walking distance of the downtown square to avoid parking concerns. The town is pedestrian-friendly and the springtime weather in the mid-60s is comfortable for walking. Dahlonega is also known as one of the most postcard-perfect Christmas towns in America.

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By February 10: Book a spring break trip to Scottsdale, Arizona

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If you’re traveling from a colder climate, there’s no place like Arizona for spring break. The sun warms the desert rocks to balmy high 70s temperatures by afternoon, and many vacation homes have a backyard pool for splashing around if the heat becomes too much. Wake up early to climb Camelback Mountain, then descend for a filling southwestern lunch downtown. Old Scottsdale, the historic arts and shopping district, has plenty of restaurants with outdoor seating, coffee shops for a second wave of energy, and wide sidewalks for ambling from one shop to the next. Find out the best spring break getaway in every state.

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By April 20: Book a Memorial Day getaway to Gulf Shores, Alabama

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The whole family will enjoy a Memorial Day trip to Gulf Shores, Alabama. Play in the sun and surf all day, then nestle into a beach-side condo in the evenings. With average highs in the mid-80s in May, Memorial Day is the best time to enjoy Gulf Shores before the heat of summer arrives. Despite the cliche, this city really does have it all: beaches, trails, a golf course, wildlife sightings, and even a zip line over the sand dunes near the coast. Find out the best beach in every state.

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By April 20: Book a Memorial Day weekend trip to Orlando, Florida

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Why not pack your holiday weekend full of beach walks and theme parks this Memorial Day? Orlando has been a favorite destination for families for a long time and it’s no wonder. Spend your first day admiring the seashells at Cocoa Beach, then take your pick of Walt Disney World, Universal Studios, or SeaWorld for the rest of your stay. Orlando also has a vibrant downtown, where weekends bring the sound of sports fans, live concerts, and even opera. Before you book your vacation rental, consider which attractions your family wants to visit so you can pick the most convenient location. These are the latest and greatest theme park attractions of 2020.

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By April 30: Book a summer escape to Myrtle Beach, South Carolina

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April might seem early for summer travel plans, but plotting your itinerary and accommodations soon will almost guarantee better deals than if you wait until after spring break. When it comes to summer sand and sun, Myrtle Beach has a lot to offer, which is why it has been attracting families for generations. This year, take a multi-generational trip to South Carolina’s Atlantic coast by booking one of the giant luxury condos with enough bedrooms to comfortably fit grandparents, parents, and grandchildren. Before your trip, learn the 13 vacation rental etiquette rules everyone must follow.

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By April 30: Book an adventurous summer vacation in Moab, Utah

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A wonderland for hikers and outdoor adventurers, Moab is the gateway city to Arches National Park plus it’s also near Canyonlands National Park, making it an ideal base camp for multi-park explorations. In Moab, you can take a sunrise hot air balloon ride over the red rock formations, go horseback riding through the valleys, and try your hand at canyoneering. Don’t worry if you don’t have the energy for adrenaline-pumping activities all day. Moab also has a nightlife replete with outdoor concerts and much quieter stargazing outings. Make sure you always pack these 10 items for any vacation rental stay.

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By May 25: Make Fourth of July plans in Washington D.C.

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While it’s easy to come up with several dazzling Fourth of July getaways, we would be remiss not to recommend the most patriotic destination of all: our nation’s capital, Washington D.C. Stop in and see the Declaration of Independence in the National Archives Museum, visit the Smithsonian National Museum of American History to see the original Francis Scott Key Star-Spangled Banner flag, and pay tribute to our forefathers and heroes at the numerous memorials. Finally, gather on the National Mall to watch red, white, and blue fireworks crackle and burst overhead. Keep transportation simple by staying downtown and walking or taking public transportation wherever you can.

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By May 25: Book a July 4 stay in Boston

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The Boston Pops Fireworks Spectacular is a free, public display of patriotism and showers of colorful sparks in the sky—in fact, it’s one of the most amazing fireworks shows in America. Located downtown, the show takes place along the Charles River, next to the waterfront trail. But of course, the Fourth of July isn’t all about nighttime fireworks. In Boston, you can immerse yourself in United States’ history by taking a guided or independent tour of the Freedom Trail, a 2.5 mile (4 km) stretch of 16 iconic and cultural American sites.

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By July 28: Make Labor Day plans in St. Joseph, Michigan

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Join dozens of other Michiganders on the shores of Lake Michigan as they celebrate the last weekend before public schools re-open for the year. The Mitten State has 3,224 miles (5,188.5 km) of lakeshore—it’s not called the “Riviera of the Midwest” for nothing—but St. Joseph is one of the easiest stretches for a weekend getaway because of its proximity to airports in Chicago and Grand Rapids. Splash in the shallows, ride the Silver Beach Center carousel, and don’t forget to grab a local pepperoni pie at Silver Beach Pizza. Discover the most popular Airbnb in every state.

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By July 28: Book a Labor Day stay in Bar Harbor, Maine

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As some of the heat dissipates near the coastline, you might feel a breath of cool autumnal air when you visit Bar Harbor for Labor Day weekend. Next to Acadia National Park, Bar Harbor is more than just a gateway city to one of the country’s most beautiful wild places. It also holds its own with friendly maritime vibes downtown, an array of lighthouses to visit, and green parks to stretch out and relax with a classic lobster roll in hand. You won’t find a better town to catch the waning light of summer than this Maine mainstay. Discover the top Airbnb rentals under $100 in every state.

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By October 21: Book a Thanksgiving feast in Sevierville, Tennessee

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What’s more American than the Fourth of July and apple pie? Maybe a roasted turkey in Dolly Parton’s hometown on Thanksgiving Day. Sevierville prides itself as the gateway to the Smoky Mountains. It’s also a central zone for parks of all kinds: Great Smoky Mountains National Park, of course, plus a theme park, aquatic park, and local parks for running and playing with the family. Whether you choose to rent a cabin or a ranch home, you’ll enjoy kickstarting the holidays in Sevierville. Dolly Parton fans will want to visit nearby Dollywood, which is on our list of wacky theme parks around the globe.

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By October 21: Plan a Turkey Day celebration in New York City

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Aside from the Thanksgiving meal itself, there’s nothing that says Thanksgiving like the Macy’s Thanksgiving Day Parade. The parade kicks off the holiday season with panache. You’ll pay a pretty penny to rent a home in Manhattan, but the soaring views and location amidst the hubbub make it all worth it. Since you will have the entire weekend to soak up the buzz of the city, plan an itinerary that goes beyond the parade and traditional Thanksgiving fare. Settle in for a sophisticated evening with The Nutcracker at the New York City Ballet. Or squeeze in a dinner or pint of lager at Rolf’s for the most magical restaurant decorations in the city.

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By October 30: Book your ski season in Telluride, Colorado

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Telluride’s iconic Western vibes and location in a box canyon at the base of the Rocky Mountains have made it a hit with vacationers at any time of year. But the area kicks into high season once the slopes accumulate mounds of glittering snow. The center of activity is the Telluride Sky Resort, known for its world-class trails and guided activities such as snowshoeing and snow biking. Look for a home rental near the gondola for easy access to the chairlift and first dibs on the slopes each morning. Don’t forget to check out the best ski resorts in all of Colorado.

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By October 30: Buy your ski passes for Sun Valley, Idaho

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Sun Valley is known for its ski culture, but it turns out that there are plenty of winter sports in this ski resort town. Before heading out for the day, choose whether you’d like to go snowmobiling, paragliding, fat biking, or—of course—downhill or cross-country skiing. The town also has a seriously busy apres-ski scene. Whether you prefer live music or a rollicking sports bar scene, you’ll find a fun way to wind down after a day of sun and snow on the slopes in Sun Valley, one of the most majestic towns in America.

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By November 17: Book a cozy winter escape in Breckenridge, Colorado

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If you’re considering a winter break getaway, try to plan the trip before Thanksgiving, when demand and costs begin to rise. Many families flock to warmer climates in December, but you might enjoy peace and quiet in Breckenridge at the base of the Rocky Mountains. Cozy up by a crackling fire, squeeze in extra holiday shopping, and then spend the afternoon playing in the brilliant white snow. A former mining town, Breckenridge has a delightfully quaint downtown lined with colorful shops and restaurants. It’s an ideal mix of small-town charm and big mountain adventures. From ski-in condos to giant mountain villas, there are plenty of vacation home rental options in this Colorado haven. You’ll want to know the signs you’re about to fall for a bad vacation rental listing.

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By November 17: Make plans to thaw out in Huntington Beach, California

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One of the best cheap winter getaways even in high season, Huntington Beach is the kind of place Northerners go to feel the sun on their faces in December. Just an hour from Los Angeles, this ocean town oozes casual charm. From bonfires on the beach to beers on the patio, you can spend the holidays watching the palms sway (instead of the snowfall) by snagging a Huntington Beach vacation rental before they’re all sold out for the end of 2020. Next, read on to see the most extravagant Airbnb listings in every state.

Leandra Beabout
Leandra Beabout is a freelance journalist and branded content writer with a BA in English education from Indiana University. She writes about travel, health, and literature for Reader's Digest, Lonely Planet, CNN, and Literary Hub, among other publications. She is also a regular contributor to Leandra is based in Indiana. Follow her on Instagram @LeandraBeabout and LinkedIn Leandrabeabout

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