7 Sensational Shoulder-Season Steals

Back to school means dollars spent on fall clothing, school supplies and registration fees for all of those extracurricular activities — and not much left in your wallet for travel. But if you have the inclination to get out of Dodge (that is, if you can find the time between chauffeuring the kids to after-school clubs and weekend sports events), you can snag some fantastic travel bargains this time of year.

“Shoulder season,” the period when the back-to-school rush prevents many families from traveling, is one of the best times to book dirt-cheap travel deals. For parents of tots, this travel period is a steal — you can easily take the kids out of preschool for a weeklong vacation. If you don’t mind your school-age kids missing a couple of days early in the year (just be sure they get their schoolwork done!), you can take advantage of autumn deals in alluring destinations like Hawaii and the Caribbean, where properties are slashing rates and rolling out money-saving fall promotions. We’re talking all-inclusive resorts for under $120 per night, free airfare, free nights, discounted luxury accommodations and plenty more. Travel deals for these regions start popping up around late August and September, and last until mid-December, before the holiday season kicks in. We recommend booking shoulder-season deals as early as possible for best availability — the hottest bargains are likely to sell out quickly!

1. Free Night’s Stay at Hyatt Aruba

With the “Three for Free” package at Hyatt Regency Aruba Resort and Casino, families can get a free night’s stay, a free room upgrade and a complimentary breakfast for two adults when staying at the hotel through December 21. This beachfront resort features plenty of perks for families vacationing in Aruba, including six on-site reataurants (all of which have kids’ menus) and a kids’ program.
Book by: December 21

2. Save 50% at Aston Hotels and Resorts in Hawaii

Aston Hotels and Resorts is currently offering a fantastic deal for families traveling to the Aloha State this fall. The chain’s “50 Days of Aloha” sale features up to half off standard rates at 25 properties on four Hawaiian Islands: Oahu, Maui, Kauai and the Big Island. Nightly rates start at just $73 — a steal for plush accommodations in Hawaii. Children under the age of 17 stay free, and kids under the age of 12 receive free meals plus free admission to local attractions. To take advantage of this offer, you must travel between August 24 and December 21.
Book by: August 23

3. Free Companion + Fourth Night Free at Airfare Atlantis, Bahamas

Take the kids to Atlantis Resort on Paradise Island in the Bahamas this fall, and get a free night and free companion airfare, plus plenty of other perks when you travel between August 15 and December 22. The chance to snag a complimentary companion plane ticket (valid on Continental Airlines flights only) means your group can instantly save hundreds of dollars on a Bahamas family vacation. In addition, Atlantis is throwing in a complimentary fourth night and an Atlantis Experience Pass, which gives access to free activities, drinks and more.
Book by: August 22

4. Save 55% at Coconut Bay Beach Resort & Spa, St. Lucia

Rates at Coconut Bay Beach Resort in the St. Lucia are dropping like falling leaves this season. Families who travel between August 26 and December 20 can save up to 55 percent on standard room prices at the family-friendly resort. Discounted rates start at $112 per person, per night — and yes, it’s all inclusive! This means unlimited meals, a kids’ club, tons of activities and even airport transfers are included at no extra charge. Kids under the age of 3 stay free, and the resort offers discounted nightly rates (starting at $29) for kids ages 3 to 17. Coconut Bay is even throwing in a $250 resort credit for guests who stay for seven nights or more.
Book by: August 31

5. Third Night Free at Fairmont Southampton, Bermuda

Thanks to Fairmont Southampton’s “Endless Summer” sale, a luxury vacation in Bermuda is significantly more affordable for budget-minded families. The deal? Travel between August 22 and October 31, and get your third night’s stay for free. This equals a savings of as much as $539 (the cost of a night in the resort’s 600-square-foot junior suite). Fairmont Southampton’s high-class perks include a free kids’ club; a gorgeous, private pink-sand beach; access to the resort’s exclusive Beach Club; two swimming pools; and luxurious, spacious rooms.
Book by: September 30

6. Save 50% at Napili Kai Beach Resort, Maui

Napili Kai Beach Resort’s “Sweet Suite Special” features half-priced oceanfront, one-bedroom suites, which are wonderfully spacious accommodations for families who need plenty of room to keep everyone happy. Rates are reduced from $505 per night to $252 for roomy digs with two separate sleeping areas, up to two bathrooms, full kitchens and even private balconies (or lanai, as the locals call it). Napili Kai Beach Resort is situated amidst acres of tropical gardens by a pristine beach on Napili Bay, one of Maui’s top snorkeling spots. This deal is good for stays from August 21 through December 14.
Book by: December 14

7. Third Night Free at Outrigger Condominiums in Hawaii

Enjoy special discounted rates in addition to free nights at Outrigger properties on Oahu, Maui, Kauai and the Big Island — this sale includes 14 properties from which to choose! Nightly rates start at $185, plus your third night’s stay is free of charge. We love Outrigger condos because they offer plenty of options for vacationing families of all sizes. You’ll find rooms with full kitchens, studio condos, plus one- and two-bedroom rooms that have separate sleeping areas.
Book by: December 21