The Best Resorts for Multigenerational Families

We’ve been traveling with my mom since the twins were born. In other words, we’ve found the best resorts for multigenerational families and rounded up some advice for any family traveling with multiple generations. Of course, we don’t always stay in separate suites, but we always book an option with at least two rooms (with doors). And, all the adults on the trip must have comfortable sleeping options. No one wants to get stuck on the pull-out sofa, right? So, here we go! Keep reading for our list of the best multigenerational resorts.

Orange Lake Resort – Kissimmee, Florida

For starters, we still say this is one of the nicest villas we’ve ever stayed in. The two-bedroom villa setup is perfect for a multigenerational family. We did stick our kids on the pull-out couch, but they also slept on the second bed in the double bedroom. Both rooms offer en-suite bathrooms, and there’s tons of space in the open concept full kitchen, dining room and living area.

You won’t find a better option as far as amenities and location. The resort boasts multiple pools with slides, lazy rivers, splash pads and scuba lessons. In addition, your kids can learn to swim like a mermaid (tail included) while you dine at one of the multiple poolside restaurants. Add to that, you’ll be a short drive from Walt Disney World, and you are all set for your next multigenerational vacation.

Williamsburg Resort – Williamsburg, Virginia

We celebrated my birthday at this resort, and my mom fell in love with the area and her private villa. We booked two villas for our family of six, and it was great for my mom. She was able to get away from the chaos of my kids whenever she needed a break. Also, we all loved the indoor pool and bowling alley.

Downtown, we got to explore the living history that Williamsburg has to offer. My kids loved the old-fashioned candy store and the traditional hot chocolate. My mom enjoyed learning about the colonial era, and we all liked walking around the beautifully manicured area. Be sure to book a carriage ride early in the day. They sell out quickly.

Holiday Hills Resort – Branson, Missouri

My mom has ALWAYS wanted to go to Branson, so we decided to go as a family. The town is so much fun. You can take in a show or explore Silver City. There are even some pretty great outdoorsy options if you prefer. We hiked the Waterfall Trail and rented a boat to spend the day on Table Rock Lake.

We booked two villas in Branson, and we had tons of space to spread out. The in-room laundry might have been my favorite amenity. My kids disagreed. They loved the indoor pool, and we spent hours splashing together. We aren’t golfers, but there’s a fantastic course on-site if you want to schedule a tee time.

Country Cascades Waterpark Resort – Pigeon Forge, Tennessee

Yes, you’ll need to book multiple rooms at this resort. The website description says each room sleeps 6, but that is generous. Two beds and a pull-out sofa can make for a ROUGH night. We booked a separate room for my mom, and she was kind enough to let one of the kids sleep in her extra bed. It was a great setup.

If you can get the sleeping arrangements set, then head outside to the fantastic waterpark. The zero-entry pool is perfect for little kids, and the slides will keep older kids entertained all day. When you are ready to explore the area, Pigeon Forge offers so much for young and old alike to enjoy. We loved the Pirates show and the Christmas shop.

3 responses to “The Best Resorts for Multigenerational Families”

  1. […] You can go do a person’s favorite thing. You can plan something that represents the date. Planning a multigenerational trip provides an opportunity for the older to relate to the younger and perhaps describe the celebration […]

  2. This is a big help for multigenerational families who will be travelling soon! Thank you for suggesting the best family-friendly resorts to visit. I love the idea you mentioned about travelling with babies/kids. We provide child-friendly, safe and convenient airport transportation services with pre-installed car seats. You can learn more at

  3. We travel multigenerational too. I’ll have to check out the Williamsburg Resort, since we have been wanting to visit there for sometime. Thanks for the suggestions!

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