Vacation rentals in Waupun

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all pictures of the property *Not suitable for parties or loud gatherings. There is a 4 person, 2 vehicle maximum. *Check out our “cottage on the trail”, closer to the lake. *As of June 2026, we can no longer accept pets. Reservations made prior will be upheld

Green Heron Cottage · King Beds · Horicon Marsh

Charming and cozy, this delightful 3-bedroom cottage sits in the heart of downtown Horicon, just moments from the scenic beauty of the Horicon Marsh with its peaceful trails and relaxing boat tours. Treat yourself to a nostalgic scoop at the beloved Ice Cream Station just two doors away, then unwind back at your private retreat. The backyard invites you to gather under the stars, where a crackling fire pit and grill set the stage for laid-back evenings, laughter, and lasting memories. Cheers!

Private Riverfront, Converted Barn *EV Charger*

Fox River Barn is located in a picturesque setting with stunning views of the Fox River in Princeton, WI. This 1940s barn has been lovingly converted into a comfortable living space with modern features and amenities, making it the perfect retreat for a romantic getaway or a peaceful escape from the city. Inside, the bones of the barn are present. From beams and rafters on the main level to the tall, gable barn ceiling. Just imagine all the different ways the barn had been used over time.

Woltring Waters Waterfront Home + Hot Tub

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Pet Friendly Antique Schoolhouse with Fenced Yard

Pond Lily is truly a unique stay; a historic schoolhouse among tranquil surroundings. Beautiful traditional craftsmanship meets all the comforts of a modern home. Pet friendly with a fenced yard. A well-stocked kitchen makes for easy home-cooked meals. The layout is ideal for small groups looking to enjoy a peaceful getaway. Snuggle up by the wood-burning fireplace in the cold months or enjoy the firepit in the warm weather. For the outdoorsman, public lands are 5 minutes away.

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Countryside Ranch Home

Quiet Country Life. NO WIFI. Take a stroll down the lane, hike through the woods watch the wildlife on the ponds. 30 minute drive to AirVenture in Oshkosh. Just a short drive to Horicon Marsh, Hoffs Meat Market, Wild Wings Bird Hunts, Horicon Ledge Hiking and so much more all with the small town feel. 1890’s stone “house” on property with the original farm barn and grainery. In addition to this home there is a Hunting lodge also located on property separate AirBNB

Haven on the Lake

Welcome to our unique A-Frame, Haven on the Lake! -1 hour from Madison -3 hours from Chicago -30 minutes from Cascade Mountain -40 minutes from WI Dells & Devil's Head Resort Nestled on a serene, five-acre lot overlooking Willams Lake, this renovated A-frame cabin is the perfect escape for families seeking peace, adventure, and natural beauty. The cabin offers a unique blend of modern amenities and old cabin charm, creating a cozy retreat in the heart of nature.

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Quiet & Cozy Cabin Across from Fox Lake

I am excited to invite you to stay in this super cozy, relaxing, & peaceful home! Enjoy a night around the fire, or a relaxing evening with your family & friends downstairs at the bar. I hope you have a great stay in Fox Lake! This is a small cabin style home updated for comfort & homey feels! There is a walk-in area & a hallway when you enter. The hallway has 1 bedroom on each side, then a bathroom & the kitchen/dining room at the end.

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.