Family-Friendly Long Weekend Escapes for Fall 2025

Each week, we're handpicking Pineapple7 exclusives for you to consider. This week, we have curated five Fall 2025 US getaways for families. When you book with us, you'll unlock VIP perks and amenities you won't receive on your own. These offers are time-sensitive and have limited availability. Blackout dates and minimum stays may apply.

Pendry Park City, Park City, UT: Discover Park City and Additional Credits

Make Pendry Park City your home base as you explore the historic mountain town and year-round playground with your family. The resort offers outdoor adventures perfect for all ages, including e-bike rentals, mountain biking, dark sky stargazing, wasatch fly fishing, and guided hiking retreats. When you stay a minimum of two nights, you'll receive daily valet parking, a one-time $100 dining credit, and a one-time $200 Compass Sports credit to put toward your next adventure. ✈️ Non-stop Flight from IAD to SLC (approximately 4 hours; 34 miles to resort)

Ritz-Carlton Naples, FL: Stay Longer and Save

Escape to the serene, elegant setting of The Ritz-Carlton Naples, Tiburón, for a sophisticated getaway with the family. This destination offers luxe amenities and an immersive water experience for a relaxing escape. The hotel offers two pools, a rejuvenating spa, an interactive kids program and two 18-hole Greg Norman designed course. Stay at least three nights and save up to 15%, plus enjoy daily breakfast for two, a $100 resort credit, complimentary Wi-Fi, and a free room upgrade upon check-in, if available.

✈️Non-stop flight IAD to RSW (2.5 hours; 24 miles to resort)

Fairmont Century Plaza, Los Angeles Pool-cation All-Inclusive

Experience the ultimate family "pool-cation" in the heart of Los Angeles (perfectly poised on the Avenue of the Stars in the heart of Los Angeles, just a short walk from Beverly Hills!) The resort provides early pool access and complimentary water and sunblock, making it a perfect spot for kids to play. Live like a Hollywood A-lister and save up to $300 daily with the all-inclusive package, which includes complimentary daily breakfast, a $100 daily hotel credit, a $150 credit for the Fairmont Spa, complimentary valet parking, and a guaranteed late 2 p.m. departure. ✈️Non-stop flight IAD-LAX (5.25 hours; 15 miles to property)

Tides Inn, Irvington, VA - Chesapeake Gold and enhanced credit

Discover a waterfront getaway in the Chesapeake Bay region of Virginia, just a short drive from the DC area. The Tides Inn offers a beautiful fall setting and outdoor adventures perfect for family bonding such as canoes, cruiser bikes (for kids and adults), hiking trails, and bocce. Enjoy a preferred rate and a $150 daily resort credit to use on unique experiences like the Fall Foliage Seaplane Tour or the Chesapeake Gold Oyster experience. 🚙 3 hour drive from Washington, DC and 1 hour from Richmond

Acqualina Resort, Miami - 4th Night Free

Acqualina Resort & Residences is a five-star property on pristine sands, offering a marine-biology-inspired children’s program for kids ages 4-12, three oceanfront swimming pools, and four restaurants. Stay longer and experience it all with a package that includes a fourth night free, a welcome amenity, daily breakfast for adults, a $45 SPA credit per person, complimentary access to the AcquaMarine children's program, and complimentary internet access. ✈️Non-stop flight IAD-FLL or IAD-MIA (2.75 hour flight; 14 miles from FLL and 19 miles from MIA)

Ready to book your upcoming getaway? Contact travel@pineapple7.com or schedule a quick discovery call to get started!