Charming Airbnbs Near Downtowns, Trails, & Water

August 24, 2023

With only a 2hr drive from Chicago or 40-60min drive from Milwaukee or Madison, Jefferson County is an ideal getaway for shopping, hiking, and time on the water. And we're filled with charming Airbnbs near your adventure of choice! From Whitewater Lake and the Ice Age Trail segments to Rock River and Lake Koshkonong, consider these vacation rentals for a unique experience.

Near Downtowns

Modern Studio 

This modern studio has its own entrance and is perfect for someone looking for a place to stay while in town for work. Located in a quiet neighborhood close to downtown, guests have easy access to Whitewater’s shops and restaurants.

The Modern Cozy Spacious Corner 

This full home is just what a family needs for a 4th of July weekend or winter getaway. Located within walking distance of downtown Whitewater (and the sledding hill, Killer Hill, if its winter!), both adults and kids will find what they need!

Pet-Friendly Industrial 2 Bedroom

This 2 bedroom unit is just a short drive to Whitewater’s downtown shops and restaurants and a short walk to UW Whitewater’s campus. Take your pup on a walk to Starin Park and check out the iconic “Witches Tower”.

Mid-Century Retreat 

This family home is located in the heart of Fort Atkinson. Walk for ice cream at Frostie Freeze or enjoy the Riverwalk downtown.

Earthy Contemporary Apartment 

This contemporary apartment rental is within walking distance to downtown Jefferson. Book your stay during Gemuetlichkeit Days and prost to Jefferson’s German heritage!

Near Hiking Trails

Mid-Century Masterpiece

This 1968 retreat home is tucked into the Kettle Moraine State Forest of Whitewater with no wifi…a supreme option for completely unplugging. Enjoy the privacy of the 18acre property or venture out to hike the nearby Ice Age Trail segments.

Kettle Moraine Cabin at Pine Knolls

This cabin rests in the pines of the Kettle Moraine State Forest of Whitewater. Located only a few miles from the Ice Age Trail and biking at John Muir Trails.

Aztalan State Mounds Cottage

This 3 bedroom cottage in Jefferson offers easy access to archaeological site Aztalan State Mounds. Hike or bike at the state park or fish the Craw Fish River.

Yurt Near CamRock 

This luxe camping yurt provides a comfy outdoor escape in Fort Atkinson. Located near CamRock Park for biking and hiking or canoe the private lake on the property. You may also glimpse Icelandic horses.

Near Water

Lakefront Estate

This “Lakeshore Lodge” is located right on Whitewater Lake. Perfect for large groups of friends or family, spend your getaway fishing, boating, or swimming and watch the sunset over the lake every night.

Restful 4 Bedroom

This home across the street from Whitewater Lake offers an expansive property with cozy firepit. Close to Whitewater Lake, Ice Age Trail, and the Kettle Moraine State Forest.

Waterfront Getaway Bungalow 

This 12 guest bungalow in Fort Atkinson is a group getaway dream. Near Rock and Bark rivers and Lake Koshkonong, you’ll enjoy all the water fun you can imagine.

Cozy Retreat

This cozy retreat home is nestled between Whitewater Lake and Natureland County Park. A great option for families, enjoy boating on Whitewater Lake or hiking and a picnic at Natureland.

Lakefront Access Cottage on Lake Koshkonong

Escape to this 2 bedroom cottage in Fort Atkinson if you need lake therapy. Kick up your feet on the back deck overlooking Lake Koshkonong and then head into town for delicious eats.

Bartels Landing Boathouse

This historic property on Rock Lake in Lake Mills offers its own pier for lake fun. Enjoy pool and ping pong or swim at Bartel’s Beach.

Rock River Vacation Rental

This 2 bedroom in Jefferson rests in a wildlife habitat! Relax to the sounds of nature or head to Rock River for fishing or boating. Not in the mood for water fun? Hang out in the furnished tree house all day!


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