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

Charming Country Cottage

Located on a quiet country road, our quaint little cottage is a lovely place to unwind, make memories, and embrace the simpler life. Featuring an open concept first floor with a cozy living space, an electric fireplace, and a well stocked kitchen. We have been working hard to create a comfortable and inviting atmosphere. Important: the cottage is located next to our home on 5 acres, if you are looking for seclusion, keep looking. We are a large work at home family. You will see and hear us.

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.

Scott Street Bungalow Ripon - Green Lake

This home is set in one of Ripons Historic Districts three blocks from a vibrant downtown full of retail shops and great places to eat and relax. Across the street from us is the Gothic mill pond water fall dam with Horner park abutting the property. We are only 6 miles from Green Lake which offers plenty of boating and golfing. Off street driveway parking is a plus with this property for boats on trailers. Our home offers two bedrooms on the main floor with 2 double size beds upstairs.

Log Cabin at Cliff Lake: Family Friendly Getaway

The Log Cabin at Cliff Lake is a place to make memories with friends and family. Watch the deer from the bay windows with a warm cup of coffee or tea before you head out for a kayak ride or some time on the swing set. With two bedrooms, space to work and a kids area with a crib, toys and books, it’s the perfect family escape. When you rent this secluded cabin, you’ll have access to more than 6 acres of land, surrounded by a small private lake, but just 5 minutes from the grocery store.

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.

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

The Shack

Enjoy 73’ of Beaver Dam Lake Shore. This 3 bedroom cottage is located right on the water front. The Shack can accommodate 6 people comfortably. With a comfortable and quiet interment, this is the perfect spot to fish, enjoy the lake and wildlife, socialize around a campfire, finally read that book by the lake while the sun is setting, creating lifetime of memories. This is what The Shack Cottage can provide for you. Not suitable for parties or loud gatherings.

Marsh Haven by Fieldview Estates

One of the few remaining private properties left on the edge of the Horicon Marsh, Marsh Haven provides a stunning view, great bird watching, and easy access to public hunting land, bike and hiking trails, and more. Stay in a spacious farmhouse for fun and relaxation. *Please be aware this home has hard surfaces and steep stairs that may not be suitable for children under 4 years of age* Private land is not available for hunting, please use public land nearby.

Updated 2BR • Work or Fun Ready • North Hwy 33

Two bed one bath on the north side of Beaver Dam. Well stock and all updated, it’s the rustic vibe without the roughing-it! One bedroom with a queen size bed, the other has a king. Both room have TVs. Wifi throughout. Washer and dryer in unit. The kitchen and bathroom are well stocked with most everything you need for a comfortable stay. On site parking is available in the driveway, Beautiful lake view. Beaver Point Lodge is rustic without roughing it!!

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.