Back-to-School Getaways Perfect for a Family Reset

Why Late Summer and Early Fall Are the Best Times for a Luxury Family Vacation

Planning a luxury family vacation in August or September comes with unexpected perks. These shoulder-season months offer milder weather, thinner crowds and lower rates — especially at popular summer destinations. With fewer tourists, families enjoy more personalized service and greater access to top-tier resort amenities.

For parents of younger children or families with flexible schedules, early fall is an ideal window to travel. Many resorts offer special promotions after Labor Day, and destinations like Cape Cod, the Big Island and Sedona are at their most beautiful during this time.

What to Look for in a Kid-Friendly Luxury Resort

Not all high-end resorts are created equal when it comes to family travel. The best kid-friendly luxury resorts combine five-star service with thoughtful details designed for younger guests. Look for properties that offer:

• Dedicated kids' clubs or children’s programming
• Family suites or multi-bedroom villas
• On-site activities for all ages (think scavenger hunts, surfing, horseback riding)
• Educational or cultural experiences
• Babysitting services or spa time for parents

Each of the properties below offers the perfect blend of luxury, comfort and family-focused fun — ensuring that every member of your group, from toddlers to teens, has a memorable experience.

The Little Nell: Aspen Colorado

Best for: Mountain adventures and elevated relaxation

Tucked at the base of Aspen Mountain, The Little Nell is Colorado’s premier luxury retreat for active families who love the outdoors. While it’s famed for ski-in/ski-out access, late summer and fall bring golden aspen groves, ideal temperatures and a relaxed atmosphere. The Little Nell Adventures concierge can craft custom itineraries that include family-friendly hikes, e-bike rentals and private fly-fishing excursions on the Roaring Fork River.

The hotel’s luxurious accommodations — including spacious suites and residences — ensure comfort for every age, and the outdoor heated pool is a hit year-round. Parents can indulge in après-style cocktails on the patio while kids sample elevated comfort food from in-room dining. Bonus: pet-friendly rooms mean no one gets left behind.

Enchantment Resort: Sedona, Arizona

Best for: Nature-loving families and wellness seekers

Surrounded by Sedona’s dramatic red rock formations, Enchantment Resort invites families to reconnect with nature in one of the Southwest’s most iconic landscapes. This luxurious desert hideaway blends outdoor recreation with five-star hospitality. Kids can join the Camp Coyote program, which emphasizes hands-on learning through activities like stargazing, sand art and canyon hikes led by experienced counselors.

For family adventures, the resort offers mountain biking, vortex tours and guided geology walks through Boynton Canyon. Parents can recharge at the award-winning Mii amo spa or enjoy a sunset cocktail on the deck overlooking the cliffs. With spacious casitas and private patios, Enchantment is perfect for those seeking serenity and space.

Four Seasons Resort Hualalai: Big Island, Hawai‘i

Best for: Beach-loving families and multi-generational trips

One of the best luxury resorts in Hawai‘i for families, Four Seasons Resort Hualalai blends island tradition with modern elegance. Its Kids For All Seasons program offers immersive experiences like Hawaiian arts and crafts, tide pool exploration and hula lessons. The resort’s seven pools — including a protected keiki (children’s) pool and a snorkeling-friendly lava rock aquarium — keep kids entertained from morning to sunset.

Multigenerational travelers will appreciate the spacious suites and villas, many of which include kitchens and private plunge pools. Parents can take part in cultural workshops or relax at the adults-only Palm Grove Pool, while the whole family comes together for oceanfront dinners under the stars. It’s the ultimate tropical escape with educational flair and luxurious comfort.

The Ranch at Rock Creek: Philipsburg, Montana

Best for: Authentic Western experiences with five-star flair

For a true luxury family vacation in the American West, The Ranch at Rock Creek offers an unforgettable all-inclusive experience. This Relais & Châteaux property pairs rugged Montana adventure with refined hospitality. Each day is filled with exciting family-friendly activities — think horseback riding, fly fishing, geocaching and archery. The Ranch Children’s Program caters to younger guests with nature crafts, mini-rodeos and pony rides.

Accommodations range from private log homes to stylish glamping tents complete with ensuite bathrooms and wood-burning stoves. Mealtimes are a culinary highlight, with locally sourced menus and kid-friendly options. With personal ranch guides, curated excursions and no screen time required, this is a rare opportunity for families to unplug and reconnect in spectacular surroundings.

The Ritz-Carlton, Half Moon Bay: California

Best for: Coastal escapes with easy access from San Francisco

Just a short drive from San Francisco, The Ritz-Carlton, Half Moon Bay feels worlds away. This coastal resort sits atop dramatic oceanfront cliffs and offers sweeping views of the Pacific. Families can spend their days exploring tidepools, roasting s’mores by the fire or cycling along the scenic Coastal Trail using complimentary bikes. The Ritz Kids program introduces little ones to the wonders of the sea with themed activities centered on sustainability and marine life.

Spacious guest rooms and suites, some with fire pits and ocean views, make it easy to relax after a day of exploring. Golf-loving parents will appreciate the two championship courses, while spa-goers can indulge in sea-inspired treatments. It’s a luxury family getaway that combines the ease of access with the beauty of California’s coastline.

The Langham: Chicago

Best for: City culture, lakefront adventures and urban luxury

Located along the Chicago River, The Langham is a standout for families seeking a luxury city escape. The hotel’s Family Getaway and Langham Kids’ Suite Experience packages turn a city break into a memorable event, complete with in-room tents, kids’ robes and slippers and curated welcome amenities. The central location puts Navy Pier, Millennium Park and the Field Museum within easy reach — perfect for curious young travelers.

Spacious suites accommodate families in comfort, and the indoor pool and wellness spa offer downtime after busy days of sightseeing. Parents will love the elevated cocktail scene at Travelle and the afternoon tea experience, while kids can delight in treats from the pink candy cart in the lobby. It’s a perfect blend of fun, luxury and convenience.

Start Planning Your Back-to-School Escape

These destinations prove that family travel doesn’t have to end with summer break. Whether you’re looking for a quick weekend reset or a longer retreat, these luxury resorts offer unforgettable experiences designed to delight every member of the family.

Looking to customize your own luxury family getaway? Our travel advisors specialize in crafting elevated, kid-friendly itineraries with exclusive perks and upgrades. Connect with an expert advisor today.