Holiday rentals in Oconomowoc

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 Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Nice 1 BR Apt, WIFI & Office, Near State Fair

This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

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.

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.

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.

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

Brand New Studio w. Private Entry + Garden Patio

Beautiful studio unit, sleeps 3. Professionally landscaped patio for morning coffee, or late night stargazing. Free parking, 3 miles from I94, W/D, fully stocked kitchenette, induction stove, microwave, deluxe coffee maker, toaster oven, mini refrigerator, WiFI, Smart TV, Wireless Printer,, private fenced yard, patio heater for chilly nights. Telescope experience available for stargazing. Perfect for the traveling professional, or couple.

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.