Holiday rentals in Town of Ashippun

Charming Historic Upper|Walk to Dining,Shops&Lakes

✨Looking for a memorable Wisconsin getaway? The Blue Belle offers a one-of-a-kind stay, blending Victorian charm with modern comforts. 📍Perfectly situated in the heart of Lake Country, The Blue Belle is located on a main street that leads you to shops, restaurants, lakes and popular wedding venues—all just a short walk away. 🗓️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.

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

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.

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.

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Stylish 1BR Downtown Oconomowoc

Enjoy a stay in this stylish one-bedroom retreat in downtown Oconomowoc. Located on the main street, the property offers a lovely view of Lake Fowler and is just steps away from shops and restaurants. It features two tandem parking spaces and requires a short flight of stairs to access. Recently remodeled, the space is beautifully decorated and designed for comfort. Perfect for a relaxing getaway or a convenient base for exploring the area.

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.

Okauchee Lakefront Cabin Escape

The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.