Planning a vacation that keeps grandparents, parents, teenagers, and little ones happy at the same time can feel like an impossible task.
Every generation has different interests, energy levels, and expectations, making it challenging to find a destination that appeals to everyone.
When I've taken trips with my extended family, I've learned that the most successful multigenerational trips aren't necessarily packed with activities from dawn to dusk. Instead, they're built around resorts that offer something for everyone, along with plenty of opportunities to come together throughout the day.
Whether your family prefers outdoor adventures, theme park thrills, or laid-back mountain escapes, these U.S. resorts are designed to bring generations together.
In this article
Paws Up Montana
Set on 37,000 acres of wilderness outside Missoula, Paws Up Montana offers a luxury ranch experience that appeals to all ages.
Families can stay in spacious vacation homes with multiple bedrooms and large gathering areas, making it easy for grandparents and grandchildren to share a vacation without sacrificing privacy.
When I visited Paws Up with my teenager, we stayed in the safari tents alongside a large family that had booked four tents to accommodate their three-generation group. The family gathered for breakfast in the common area before setting out on adventures that included cattle rides, whitewater rafting, and archery. Little kids stayed behind at camp to play in the river with their grown-ups, and then everyone gathered at the chuckwagon dinner to share their favorite experiences from the day.
Evermore Orlando Resort, Florida
For families planning a Disney vacation, Evermore Orlando Resort offers a refreshing alternative to traditional hotel rooms.
The property functions much like a regular resort but also has vacation homes, which is where my family stayed. They range from a few bedrooms to massive estates capable of accommodating extended families under one roof. Our home had bunk-bed rooms, ground-floor king bed rooms that would be perfect for grandparents, and gathering spaces on each floor. I especially appreciated how each bedroom came with an attached private bathroom.
The centerpiece of the resort is an 8-acre lagoon where guests can swim, kayak, paddleboard, and relax on sandy beaches. Located just minutes from Walt Disney World, the Evermore allows families to enjoy the theme parks during the day and retreat to spacious accommodations in the evening.
Sunriver Resort, Oregon
Located in central Oregon, Sunriver Resort is ideal for active families seeking a mix of outdoor recreation and resort amenities. The sprawling property offers vacation rentals, lodge rooms, and homes that are well-suited to larger groups.
Miles of paved bike trails connect guests to pools, playgrounds, golf courses, and nearby natural attractions. Families can spend their days biking together, floating the Deschutes River, horseback riding, or exploring nearby waterfalls. The variety of activities means every generation can customize their vacation while still coming together for meals and shared adventures.
Mountain View Grand Resort & Spa, New Hampshire
Families looking for a classic New England retreat will find plenty to love at Mountain View Grand Resort & Spa in the White Mountains. The historic property combines old-world charm with modern family-friendly amenities.
When I visited with one of my kids, we had a hard time choosing whether to take a dip in one of the pools, visit the barn animals, or play a round of golf. The resort's working farm is especially popular with younger children, while grandparents will appreciate the slower pace and beautiful surroundings. For parents who have a chance to get away for a few hours, the spa is not to be missed.
When you're ready for some time outside of the property, I recommend you book seats on the Mount Washington Cog Railway, a classic White Mountains experience that takes you to the top of the Northeast's highest peak.
Dollywood Resorts, Tennessee
Located in Pigeon Forge, Dollywood’s DreamMore Resort and Spa and Dollywood’s HeartSong Lodge & Resort are designed with families in mind. Inspired by the Great Smoky Mountains, the properties offer family-friendly accommodations, communal gathering spaces, and easy access to Dollywood and Dollywood's Splash Country.
You won't have to leave the property to find something to do, as there are indoor and outdoor pools, crafts and activities, roaming performers, and marshmallow roasts. For those who want to experience the area's beauty, the Smokies provide opportunities for hiking, scenic drives, and wildlife viewing. This combination of outdoor recreation and family attractions makes the Dollywood Resorts especially appealing for groups traveling with multiple generations.
The Shortcut
Room layout matters for multigenerational groups. Look for properties with ground-floor primary suites for grandparents and bunk rooms for kids, like at Evermore Orlando or Paws Up Montana.
Variety in on-site activities is important. Sunriver Resort and Dollywood Resorts both let teens bike or hit the water park while older family members enjoy the pool or a round of golf.
A shared evening activity brings generations back together after a day apart. Think chuckwagon dinners at Paws Up or marshmallow roasts at Dollywood.
