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

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

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.

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!

Local Landmark MV / Coffeehouse / Kettle Moraine

Experience a luxury-style stay above the iconic Coffeehouse. Stay where every day begins with an Artisan Café and ends with a scoop of real Wisconsin ice cream. Nestled in the heart of the Kettle Moraine, our Airbnb offers comfort, convenience, and easy access to the area's best outdoor adventures and small-town charm. Proudly recognized as "Top Airbnb Stays Near Fond du Lac." by the Fond du Lac Reporter Travel Section. Google CBS 58 for a story on our historic Coffee House.

Cozy 1 bedroom | plus pull out sofa sleeper

Relax in this comfortable and newly refreshed 1-bedroom getaway featuring a queen bed plus a pull-out sofa, perfect for couples, small families, or friends traveling together. Enjoy a Smart TV with Netflix included, fast access to local attractions, restaurants, shopping, and the lake — all just minutes away. The home also features: • Spacious backyard perfect for relaxing outdoors • On-site laundry for added convenience • Comfortable living area with plenty of space to unwind

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.

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.

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!!

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.