- Exploring the hidden gems of Western Wisconsin—curating unforgettable stays and sharing the places locals love most.
Traveling with family is never just “booking a room.” It’s figuring out where the five-year-old will actually fall asleep, whether Grandma can get to the car without a flight of stairs, and how to keep the kids busy while the grown-ups finish their coffee.
So instead of a list of rooms, we built this guide around the reason you’re coming. Find your trip below, and we’ll tell you exactly where we’d put your crew.
You’re in town to see the grandparents, catch a game, or just be together for a few days. You want something easy, comfortable, and close by, where everyone gets a real bed and you can come and go without a fuss.
The Florida condo is one of the cleverest layouts we have, and parents love it. It’s a one-bedroom condo with a full kitchen, a living room, and a bedroom with its own private bath. In the bedroom, there’s a king bed for mom and dad and a twin bed right alongside, perfect for the little one who isn’t quite ready to sleep in another room. Out in the living room, what looks like a cozy reading nook is actually a proper twin bed, so an older sibling gets a spot of their own.
With a full traditional kitchen, you can make pancakes in your pajamas, pack snacks for the day, and skip a restaurant meal or two. Add a bright, sunny Florida theme and an electric fireplace, and it’s an easy home base for a weekend of family visits. Read more in our Florida condo spotlight.
Two queen beds and a whole lot of country music charm. The Tennessee room is a simple, comfortable fit for a family of four, with a country music and Elvis theme the kids will get a kick out of.
Why the Harbor works for families: you park right outside your room, so unloading the car seats, the cooler, and the stroller takes two minutes, not twenty. And for dinner, Philander’s is right next door.
The ceremony’s downtown, the reception runs late, and someone still needs to get the kids to bed. You want to be close to everything, with enough room that nobody’s sleeping on the floor.
At 600 square feet, the Trimbelle is The Port’s largest suite, with two king beds, so parents and kids each get a real bed. There’s a bar-height counter with two stools for breakfast or a quick snack, a coffee and tea bar for the morning after, an electric fireplace, and a tub-shower combo that makes bath time easy.
Best of all, you’re steps from downtown Prescott and the river, so you can walk to the wedding, walk back to put the kids down, and walk back again for the dancing. Learn more about The Port of Prescott.
This is the trip where the adults want to celebrate and the kids want to run. You need space for both.
The Diamond is a two-bedroom, two-bathroom condo right on Broad Street in downtown Prescott, with two king bedrooms and a queen sofa bed, so it sleeps six. There’s a full kitchen with a coffee bar and counter seating, a cozy living room with an electric fireplace, and a glam room with four hair and makeup stations for the grown-ups getting ready for a night out.
Then there’s the part the kids will talk about for weeks. Guests have access to the game room, stocked with five arcade machines, ping pong, darts, and a 50-inch TV, plus a 2,000-square-foot rooftop with a fire table and views over downtown. The kids get their arcade, the adults get their fire table, and everyone wins. It’s why so many families book the Diamond for birthday weekends.
If your crew needs a full-blown adventure, head a little over an hour north to Taylors Falls and St. Croix Falls, where the river cuts through dramatic rock cliffs.
Wannigan Point Cabins are five log-sided cabins with knotty pine interiors, full kitchens, fireplaces, and laundry, just north of downtown Taylors Falls. They’re rented by the night, weekend, or week.
From there, the fun is close by. Wild Mountain has an alpine slide, a summer waterpark, and go-karts. Interstate State Park has glacial potholes to explore and rocky trails right along the river, and kids can meet the animals at Fawn-Doe-Rosa Wildlife Park in St. Croix Falls. Climb on giant sculptures at Franconia Sculpture Park, which is free, then finish the day with burgers and mini golf at The Drive In, a 1950s classic in Taylors Falls. Many of these are seasonal, so check hours before you go.
For families who’d rather trade city noise for wide-open space.
Lost Creek Retreat is a modern country cottage tucked into an apple orchard in the rolling hills outside Pepin, and it’s one of the most-loved stays in the region, with a 4.98 rating from more than 550 reviews. It was even featured in Martha Stewart Living. Walk through the orchard and along the creek, build a fire in the wood-burning fireplace, and make s’mores at the fire pit.
Good to know: it sleeps four, with a king and a queen in an open loft upstairs, so it’s best for families who are happy sharing a space.
For little ones who just want to run, throw rocks in the river, and swing until dinner.
Cedar Ridge Resort sits right on the Great River Road with about 300 feet of Mississippi River shoreline and a riverside playground. Choose from larger units or cottages, all with kitchens, bathrooms, decks, and fireplaces. It’s the kind of place where the kids are outside before breakfast and you finally get to drink your coffee while it’s hot.
The best family trips aren’t the ones with the most packed into them. They’re the ones where everyone sleeps well, laughs a lot, and wants to come back next year. đź’™
Make downtown Prescott your home base and book direct with us: The Port of Prescott for boutique king suites steps from the river, Port After Dark for romantic suites made for couples, The Harbor Hotel for themed rooms and extended stays, and The Cove Guest House for downtown condos and group getaways.
