Holiday rentals in Oakfield

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 of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay. *Check out our “cottage on the trail”, closer to the lake.

Woltring Waters Waterfront Home

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

East Side Reside - Sleeps Five!

20 minutes to EAA, and 30 minutes to Elkhart, this spacious townhome offers TWO Queen-Sized bedrooms and a full-sized sofa to sleep (5) comfortably, a desk to work at, two bathrooms, and a fully stocked kitchen to prepare anything you need! Enjoy 500 Mbps fiber internet as well to work from home! *TOP ATTRACTIONS NEAR US* - Elkhart Lake (17 mi) - EAA (20 mi) - Road America (16 mi) - Whistling Straits (26 mi) - Lake Winnebago (2.1 mi) - Lake Michigan (37 mi)

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Beautiful 2-Bedroom Duplex

Enjoy a home away from home in this stylish and centrally-located duplex. Family and small pet friendly, this newly renovated home has a backyard porch and one acre yard. Inside, you will find a stocked kitchen, one king-size bedroom and one queen-size bedroom, complete with two air mattresses and electric pump to accommodate additional guests. The living room is comfortably furnished, including a desk and WIFI.

Milk House Cottage

Once a small barn, now a unique guest house surrounded by trees and nature. A secluded setting, yet right on the edge of the city and in close proximity to three colleges. Not far to Fond du Lac Loop bike and walking trail. Also close to grocery stores and great restaurants. Explore the nature area on the property! Out of consideration of all guests NO pets are allowed.

The Little White Cabin, Fox Lake WI

This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!