Holiday rentals in Town of Ashippun

Beautiful Oconomowoc Log Home on 5.7 acres

Beautiful fully furnished non smoking Cabin 5.7 acres wooded lot in Ashippun, 6mls/Erin hills, 2mls/deer track, 8mls lac labelle golf course wedding venue Great room: 1couch & 1chair,natural fireplace 2 full bathrooms,4 bedrooms & 3 floors:upstairs, grnd,basement; recrm, kitchenette, bdrm , 2 couches, pool table. Balcony Office/futon couch, pullout leather couch,1 bed Mastr closet,2 pullout single matrices in bsmnt, Swing set,sandbox, tree house, 2 fire pits, Back deck,grill, patio furniture

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.

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

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

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.

Pewaukee Serenity Cottage: Whimisical by the Lake

Unplug, unwind, and savor the tranquility of the lake, just a stone's throw away from our inviting cottage. Offering an open-concept layout, this is your ticket to carefree living at its finest. Your dream escape to Pewaukee awaits. Secure your spot now and immerse yourself in the harmonious blend of relaxation, adventure, and comfort that our charming cottage promises. It's time to create memories, recharge your spirits, and rediscover the joys of small town living.

Inlaw Suite with Downtown Charm

Unbeatable Historic Downtown location. Duplex-like entry to your key-access 300sf downstairs suite, full kitchen/bath. Walk a quiet neighborhood to the park, or two blocks over for Mexican food! <1 mile to the art hub of downtown - enjoy the summer farmer's market, or walk along Fox River! Minutes from convenience/department stores/more parks, 10 mins to I-94, <20 min to Pewaukee lake, <30 mins to Milwaukee/the airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.*

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes 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.