Best Fall Getaways With Toddlers and Preschoolers

If your kids are too young for notebooks and no. 2 pencils, then it's a great time for a family vacation instead. For families with preschoolers, late August through mid-October is perhaps the very best time of year to grab a getaway at a top family resort, as back-to-school prices tumble and the focus shifts to younger kids. 

Here’s a sampling of destinations that make fall a special time for preschoolers by offering activities and events especially for the under-5 crowd, while also offering parents some much deserved R&R and sweet price breaks:

  • 01 of 05

    Winnetu Oceanside Resort: Martha's Vineyard, MA

    Winnetu Resort Parent-Toddler Program
    Winnetu Oceanside Resort

    When big kids head back to the classroom, Martha's Vineyard's luxurious Winnetu Oceanside Resort offers a complimentary Parent/Toddler Program in September that allows parents and kids to participate in a variety of activities geared towards the many stages of your child’s early development.

    Check rates at Winnetu Oceanside Resort

  • 02 of 05

    Smugglers' Notch: Jeffersonville, VT

    Smugglers' Notch

    This award-winning family ski resort offers fantastic active vacations year-round, and in the fall it really rolls out the red carpet for younger kids. The AutumnFest Package lets families with small children get in a good mix of family time and adults-only time, thanks to an exceptional children’s program (infants through 5-year-olds), a nice roster of adults-only hikes and walks, and many family-together activities. Pay for three nights and get the fourth for free.

    Check rates at Smugglers' Notch Resort

  • 03 of 05

    Club Med Sandpiper Bay: Port St. Lucie, FL

    Club Med

    Rates tumble after August at this family-friendly all-inclusive, and kids under age 4 always stay and play free. Club Med's only US property is one of our picks for America's best resorts for babies and toddlers, with extensive and excellent supervised programs for children as young as 4 months old.

    Check rates at Club Med Sandpiper Bay

  • 04 of 05

    Franklyn D. Resort: Runaway Bay, Jamaica

    Jamaica All-Inclusive Resort with Vacation Nannies
    Franklyn D. Resort

    This friendly Jamaican resort makes our list of fabulous vacations with babies and toddlers because it offers something parents of little ones can't resist: a dedicated "vacation nanny" for your entire stay. More pluses: All-inclusive pricing and accommodations in one- to three-bedroom suites that are considerably larger than you find at many Caribbean all-inclusive resorts. 

    Check rates at Franklyn D. Resort

    Continue to 5 of 5 below.
  • 05 of 05

    Beaches Resorts: Four Caribbean Locations

    Beaches Resort

    The Beaches chain of kid-friendly all-inclusive resorts is heaven for the preschool set thanks to its partnership with Sesame Street. This fall there's a brand new line-up of special activities, including puppet-making, art workshops, fireworks, and live stage shows with favorite characters. Prices during this window are significantly less than in peak periods, plus there is an array of special offers.