Planning a vacation with your extended family or a group of friends is an exciting prospect, isn’t it? Before you embark on a multifamily vacation, there’s one crucial decision you need to make: finding the perfect place to stay. Trust me when I say that choosing the right accommodation can make or break your trip.
Picture this: a cozy retreat where everyone has their own space, yet common areas foster togetherness and camaraderie. A place that caters to the diverse needs and preferences of all the individuals in your group. Sounds like a dream, right? Well, good news. In this blog post, I’ve done the legwork and found outstanding places to choose from…and they’re all in the Midwest! It’s just a road trip away.
Whether you’re planning a waterfront getaway or fun in the city, I’ve got options for each. Let’s start daydreaming for the next big trip!
Multifamily Vacation Homes
Staying In Chicago, But In A Cabin
Where: Chicago, Ill.
Chicago is one of my favorite Midwest cities for many reasons, but a big one is that there are so many things for families to enjoy there. I love staying in a downtown hotel as much as the next person, but there’s something about having a whole luxury cabin just for your whole group. There’s a five-bedroom cabin (yes, cabin) in Chicago, with a sauna, game room with a pool table and foosball, and a hot tub, plus plenty of space to hang out.
Stay In A Pink House In Indiana
Where: Michigan City, Ind.
Sharing Lake Michigan with Chicago in Illinois, is Indiana. It’s John Mellencamp’s home state, so of course one must seek out a pink house. I found a lux home in Long Beach fit for Barbie, with its bright pink exterior. It’s huge – six bedrooms plus a coach house – with amenities families are going to love. There’s a sports room in the basement and a hot tub outdoors. The home comes with use of a golf cart, so you can zip over to Lake Michigan or Beachwalk Resort.
Clear Lake North Shore Getaway
Where: Clear Lake, Iowa
I have a few lake getaways in Iowa that I love, but few places can compare to Clear Lake. From lakeside restaurants to three beaches, it’s a small town summer getaway with just enough activities to not get bored but never get overrun by crowds. I found a five-bedroom stunner that’s sits on North Shore, with a hot tub view to die for. The rental also comes with two kayaks and bikes.
Game On In Iowa
Where: Waukee, Iowa
Some homes are just designed expressly for multiple families. Take this place in Waukee (just outside of Des Moines). It sleeps up to 26 people, has a game room that kids may never leave, plus an assortment of yard games and a hot tub in case they actually do step outside.
Des Moines and West Des Moines has a lot to explore, and near this home, there's Jordan Creek Mall, Smash Park, and Living History Farms. It's also not too far from Adventureland and downtown Des Moines.
Gorgeous Lodge Near KCK
Where: Overland Park, Kan.
Kansas City – both the Kansas side and the Missouri side – is a large metro area that bumps up to several communities. Rustic Barr Oak Lodge Retreat is in one of those communities, Overland Park, and it really feels like a forest getaway while being pretty close to all of KC’s attractions. The lodge sleeps 12 (with the option of renting the carriage house for even more space). The gorgeous home has three patios, fire pit, and a hot tub that looks onto a waterfall.
Traverse City Lakeside Stay
Where: Traverse City, Mich.
One of my favorite areas to explore in Michigan is near Traverse City. It’s a gorgeous area and the city itself is wonderful. Find yourself a rental near there and you’re set. Take Waterfront Silver Lake Home, with its five bedrooms and private beach. It’s 15 minutes from downtown Traverse City, and yet you get the perks of lake life with use of kayaks and SUPs.
Nature Calls In Michigan
Where: Grant, Mich.
It's hard to match the beauty of Michigan, and the area near the Muskegon River is a prime example. For families looking for adventure outdoors, this four-bedroom home awaits. It has its own private beach for swimming, and the river itself is popular for tubing.
Minnesota Waterfront Getaway
Where: Champlin, Minn.
The land of a thousand lakes has a lot of waterfront rentals to choose from. Located about 40 miles north of the Twin Cities, the Manor on the River is a six-bedroom rental in Minnesota that comes with watercrafts to enjoy – pontoon, kayaks and a jet ski. Some of the rooms open to balconies! Plus, there’s a hot tub.
Family Getaway Near Twin Cities
Where: Mendota Heights, Minn.
This five-bedroom Minnesota home is not for those seeking time in nature. This large home is for those who plan on going to Mall of America, Nickelodeon Universe, and fun in the Twin Cities. Some of the extras in the home that families will love include a heated outdoor swimming pool and a hot tub.
A Missouri Lake Vacation
Where: Linn Creek, Mo.
Lake of the Ozarks is the ultimate vacation destination in Missouri. There’s so much to do there, if you ever get bored of lake fun. Bringing along a big crew? This five-bedroom lakeside retreat sleeps 26 people, plus has its own pool and hot tub. It’s great for families since one room has four twin bunk beds and another has four queen beds. Its location is also a draw. It’s 7 miles from a waterpark.
Family Fun Near Branson
Where: Hollister, Mo.
If you can snag a vacation home like this six-bedroom home near Branson, your family vacation is going to be easy to plan. You can enjoy all the Branson ammenities (fun shows, Silver Dollar City, Branson Landing, and tons of attractions), without the constant traffic. Plus, this home is located within walking distance of beautiful Table Rock Lake!
The home is located in Branson Canyon, so you'll have access to the community's pool, sprayground, and playground, too.
Note: This place is also dog-friendly.
An Oasis In Downtown Omaha
Where: Omaha, Neb.
As the state’s largest city, Omaha is packed with world-renowned attractions, many of which are downtown. The seven-bedroom Downtown Omaha Oasis is a unique rental with an awesome rooftop with a hot tub putting green and space for yard games like bags and badminton. Indoors, there’s a multilevel movie theater and arcade room.
Family Vacation In The Black Hills
Where: Hill City, S.D.
Want to see Mount Rushmore on the next family vacation to South Dakota? The Mickelson Trail Lodge is a good spot given its Hill City location near the monument. The area of the Black Hills this place is located is near other great outdoor adventures, like the 109-mile Mickelson Trail obviously, as well as my favorite state park, Custer State Park, as well as a couple National Parks. That is, if you ever leave the lodge. It’s great for traveling families, with six rooms, pool and a rooftop hot tub.
Rusty Lantern Lodge Getaway
Where: Lead, S.D.
There's a gorgeous new 7-bedroom, 7.5-bathroom cabin that just opened in July 2023. There's plenty of space for more than one family in the home, plus you get access to the community's two pools (one is heated year-round).
This is in a remote part of South Dakota, so if you're looking for low-key family time, this is the place. But you're not too far from sight seeing, if you're worried about that. Deadwood is about 5 miles away, and Mount Rushmore is about 40 miles away.
Large Cabin Near Wisconsin Dells
Where: Wisconsin Dells, Wis.
Besides cheese and beer, the first thing that comes to mind when thinking about Wisconsin is Wisconsin Dells. You could stay at one of the many waterpark resorts or, hear me out, you could get a place that accommodates all the families in your group. The Legendary Moose Lodge is a five-bedroom cabin located about 5 minutes north of all of the Dells. Not that you’d want to leave the scenic location or jacuzzi, but the cabin is also near Christmas Mountain Village and Cascade Mountain.
Tips for headache-free multifamily vacations
I’ve experienced the best of vacationing with multiple families…and a bit of the worst. From a weeklong Outer Banks stay with family to a quick weekend getaway to Kansas City with kids and girlfriends, I’ve tried it all. Here’s what I’ve learned:
- Plan time with the whole group and time with just your family. The whole point of staying in one place is to have all that time together, right? But I guarantee that you will need some time apart, so make a plan with everyone that there will at least one outing on your own. For one thing, not everyone has the same interests, so this will allow you to do something you really want to do with your family even if it’s not a crowd pleaser.
- Agree on the meal planning ahead of time. It’s fun to have meals together, but it’s not fun to do all the cooking for everyone and the cleaning up. So I recommend planning out who preps for each meal. And decide on who is bringing what food and drink items so you have what you need, but not like, five jars of peanut butter and no bread. And if you decide to do the grocery shopping together once you arrive, split the costs afterward.
- You’ll probably need more bathrooms than you think. Do I really need to go into the reason behind this one?
- Read the house rules. Avoid unexpected added expenses, and read the house rules carefully. Do you need to clean up and take the trash out before you leave? Is there a quiet hour enforced? Do you need to strip the bedding at the end of your stay? Each host is different when it comes to having guests in their rental home, so always check the rules.