Holiday rentals in Ashippun

Maple Cottage Retreat

Come discover the tranquility of our charming Maple Cottage Retreat. Nestled among tall mature trees, this spacious retreat offers ample room to breathe in the fresh, crisp country air and unwind in a setting that feels like a true haven. With tall mature trees surrounding the property, you'll have all the space you need to explore and take leisurely strolls. The interior exudes warmth and comfort. Adorned with tasteful decor, it strikes the perfect balance between modern convenience and charm.

JOE’S PLACE near Erin Hills, Bowery, Hartford WI

Minutes from Erin Hills golf course, site of the 2017 Open! Cozy yet spacious garden level space sleeps up to four. There is a private bedroom in the unit with a queen sized bed as well as a twin sized bed tucked around a corner in the living room area. There is also a couch and a roll away bed if needed. Enjoy pool, ping pong and air hockey. There is a kitchenette and bar area with seating. Fun and games in the country! This is a lower level apartment, there is a flight of stairs to access.

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

Stylish Historic Upper+King Bed/ Walk to Downtown

Looking for a memorable Wisconsin vacation experience? The Blue Belle is in the heart of Lake Country in a small town where you’ll find both adventure and relaxation! Located on a main street that takes you right to shops, restaurants, activities and wedding venues. All within walking distance. ✨Traveling with a larger group, your preferred dates taken or traveling with a furry friend 🐶? Browse our host profile for the details on other listings in the area.

Cheerful cottage in the middle of the Kettles.

Welcome to the "Middle House", where you're minutes from civilization yet you feel in the middle of nowhere. Step out the front door and hop on the Ice Age Trail, head south to Holy Hill and explore the Basilica or head north to Pike Lake State Park and enjoy the beach just minutes from the front door. This 2 bedroom fully remodeled cabin is warm and inviting, a great place to relax after your adventures in the "Middle" of the Kettle Moraine Forest.

Watertown Family Retreat

The perfect peaceful place for families, couples, or individuals to relax during their stay. You will find places for a quiet cup of coffee in the morning, family meals together, and even toasting marshmallows for s'mores at the fire pit as the sun sets and the stars come out. Before turning in, maybe you might want to take a short ten-minute walk down to the bridge over the Rock River and see the moon reflected over the water.