7 Off-Season Getaways You Should Book Now

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September usually signals the close of summer, but the off-season fall deals are just getting started. Here are our favorite off-season getaways you should book now.

September signifies a new start to the year for some; the kids are in school, back to the grind at work and the summer is over. But is it really? The official end of summer is September 21st, so squeeze every last drop out of summer 2019 by taking advantage of these travel deals where the prices drop drastically post Labor Day and run through the rest of fall.

Whether you’re looking to enjoy a long weekend (I’ve got my eye on you, Columbus Day) or you’ve saved up a week of your vacay to take advantage of quiet beaches and resort towns. Here are a few to consider this fall for an endless summer quest.

Ocean City, MD

While Ocean City is energetic, loud, and busy during the summer, it's open, quiet, and gorgeous in the fall (mid-September through late November) and September is commonly known as the “Locals Summer.”

Around then, visitors can take advantage of discounted rates and lots of valuable seasonal perks at the Dunes Manor. They can also enjoy sunny days and beautiful breezes as they stroll on the Atlantic Avenue boardwalk, which stretches for 2.5 miles and begins at the edge of the Dunes Manor’s property.

Ocean City has many exciting events that take place from September through autumn, like Island Wine Fest, O.C.Toberfest and Sunfest, where you can expect four days filled with music, food and activities for all.

Breckenridge, CO

Just ninety minutes from Denver, Breckenridge, Colorado, is an excellent example of a destination where there deals are to be had after the kids are back in school. That paired with cooler temperatures and fall leaf-peeping colors make it a desirable budget destination during off-peak season.

The lodging is less expensive post-summer and before ski season gets into swing. For example, the LOGE Breckenridge has 38 rooms with deals for as low as 100 bucks per night. They also have fire pits right outside next to some of the best trails access outside of Breckenridge, including the famed Colorado Trail.

Located at 9,600 ft. above sea level, this charming and historic town is one of the first in Colorado to say hello to fall. Miners came to Breckenridge in search of gold, and much of the town’s Gold Rush history can be experienced on the town’s 60+ miles of interconnected trails. Perfect for post-Labor Day hiking, mountain biking and horseback riding.

Block Island, RI

A quick ferry ride from mainland Rhode Island or from the tip of Montauk, New York, Block Island has a charming old-timey feel where small, family-run businesses reign supreme. Though many visitors flock to Block Island in the summer, local insider intel has long advised that September through October is prime time.

There’s more availability with the same quintessential summertime New England feel. The island is significantly less crowded in the fall, pushing the hotel prices down significantly.

The Harborside Inn offers prices under $200 through the weekend, but they also offer a “Discover Block Island” Midweek Package for two nights at $369 in September. This deal includes two round-trip ferry tickets with beverages, a welcome gift bag and dining vouchers worth $100 at Mohegan Cafe & Brewery in Old Harbor. You’ll also have access to bikes and beach chairs for your entire stay. More than 43% of Block Island is preserved in perpetuity as open space, making it the perfect beach destination to explore by bike!

Sag Harbor, NY

It’s well known that the Hamptons are the playground of the rich and famous. And while that contributes to higher prices during the summer, why not just skip the crowds and high price tags and head to Sag Harbor during shoulder season for a quiet retreat in this beach haven?

Relish in local wineries, shopping, museums, clamming, boating, and local year-round restaurants. Book a weekend at Baron’s Cove in Sag Harbor; prices drop in the fall to under $200 per night. Get major nautical vibes from the sweeping views of the majestic marina from your hotel room or from the on-property restaurant. They even have a pet-friendly program, so you can bring Fido to run on the beach. Don’t worry; they supply the bowls, bed and treats!

Cape May, NJ

Cape May is a charming seaside getaway offering the perfect beach-town trip in the fall. Explore this Victorian town by foot or bike and enjoy mouth-watering, farm-to-table dining, family-friendly fun and shopping (hey, the best sales are in the off-season!). Hotel pricing plummets in September to around $125 per night or less depending on your location.

For one, the Beach Shack (cutest name ever?) has affordable rates at this whimsical hotel with a Hawaiian-themed atmosphere. The property is also home to the Rusty Nail, Cape May’s legendary hangout for lifeguards, surfers and other beachgoers. Get ready to relax, the hardest decision you’ll be making is if you should swim in the pool or ocean. Am I right?

Brainerd, MN

Hello, Minnesota! Crunching leaves, crisp air, trickling rivers and beautiful overlooks: there’s no denying that Minnesota is one of the best places to experience fall. And many resorts in Minnesota drop their rates this time of year, making it easier on the pocketbooks to experience all the season has to offer.

Madden’s Resort on Gull Lake offers visitors a chance to soak up the remaining days of summer with prices as low as $119 per night. Pass your time on the lake with boating, fishing or paddle boarding and pretty much any water activity you can imagine. Outside of lake attractions, you can go zip lining, visit local breweries or go biking and hiking through the many trails in the Brainerd Lakes Area.

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