Holiday rentals in Cooksville

#301 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old McFarland House This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Cozy Lake Cottage With The Best View & Pontoon!

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

The Allen Creek Apt. Historic Downtown Evansville

Experience stylish comfort in this centrally located apartment in Historic Downtown Evansville! Situated above a trendy coffeehouse with a welcoming atmosphere! This upper-unit apartment sits next to Allen Creek, making it easy to explore the outdoors—bring your bike and ride the Ice Age Trail, which runs through town! You’ll be within walking distance of charming shops and restaurants, and just a 25-minute drive to downtown Madison, or Alliant Energy Center, hope you enjoy your stay!

Cozy Apartment Close to Downtown Janesville

This welcoming 1 bedroom apartment is located close to downtown Janesville, the city of parks. It has been updated throughout and has all the amenities necessary for a very comfortable stay, including a gas grill in the wooded back yard. It even has off street parking. You can easily walk to the Janesville Performing Arts Center and continue downtown and enjoy the Saturday morning Farmer's Market, shopping, restaurants and bars. Access to the Bike Trail is only a few minutes away.

Vast Lake Koshkonong Views from Pier, Deck, & Home

Our 2 Bedroom, 1 Bathroom House is located directly on the shores of Lake Koshkongong. The back deck overlooks thousands of acres of lake with endless lake views. Just steps off the deck, one can enjoy the grassy landscape leading to the lakeside fire-pit. Then continue out onto the end of the 140 foot top notch pier. The pier (seasonally of course) includes a bench on the end and stairs into the water so that you can take a refreshing swim on our sandy bottom shoreline.

Le Gallus Palace - A Tiny House

Escape to Le Gallus Palais, a cozy tiny house on a peaceful farm just 20 minutes from Madison, WI. Surrounded by farm fields, and a chicken yard, with access to a spiral orchard with tame ducks and a koi pond, this private retreat offers charm, comfort, and serenity. Enjoy a restful stay with a comfy bed, kitchenette, and nature all around. Perfect for a romantic getaway, solo retreat, or creative escape. Get the best of both worlds - country vibe with modern amenities.

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of the private lake access Buoys UP! offers.

Fresh & Bright Apartment Getaway in New Glarus

We would like to welcome you to our bright newly built 2nd floor above garage apartment. Located in a family friendly neighborhood, just a 10 minute walk to downtown where you will find delicious dining, unique shops and historical sites everywhere you turn. Jarod and I with our kids live in the main house. We love giving our guest privacy but may run into you as we are enjoying the weather as often as we can with our kids running around enjoying their childhood.

Bees on Main: sweeter than ever

Located in the heart of Stoughton's Downtown Historic District, "Bees on Main" is a lovingly renovated upstairs apartment. You'll find the Opera House, Chorus, and Stoughton's wonderful shops, restaurants, pubs, and galleries only steps away. The Yahara River and Fairgrounds are within a few blocks, and there's space on the private deck to safely store your bikes or kayaks if you want to enjoy the great outdoor activities and nature surrounding Stoughton.

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!