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.

A-frame in the Pines

"Up North" cabin decor with modern amenities. Cute A-frame cabin nestled amongst mature red & white pines. Outside space to run & play or relax by the campfire or fireplace inside. Chargrill available. Bring your own charcoal. Living room with TV, dining area, kitchen & pantry, bathroom, & bedroom with a queen size bed on main level. The "loft" upstairs has 2 bedrooms, 1 with 2 twin beds , & the other space with a queen size bed and a reading area that opens up to your own private balcony.

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.

Dogs Stay Free! Lakefront Bungalow with Dock

Corsa's Pillowfort — a waterfront bungalow on the 2,800-acre Lake Sinissippi in Dodge County, minutes from the famous Horicon Marsh and less than an hour from Madison or Milwaukee. Sleeps 3 with a king bed plus sofa bed, eat-in kitchen, and full bath. Private dock and 2 kayaks (summer season) right outside your door. Pet friendly with no pet fees — bring your dog along! At 600 sq. ft., it's the perfect lakeside getaway for couples, small families, or solo travelers looking to unplug.

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!

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.

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.