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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!

Charming Historic Upper | Walk to Downtown & Lakes

Stay in a piece of Oconomowoc history. Whether you're here for a lakeside wedding or a quiet retreat, The Blue Belle offers designer interiors and comfy beds our guests love all steps from downtown This charming town offers the perfect blend of adventure and relaxation, with shops, restaurants, wedding venues & activities all within walking distance. Browse our host profile for additional listings if your preferred dates are unavailable, are traveling with a larger group or a furry friend.

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

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.

Cozy cottage in the heart of Lake Country

Entire cottage in Lake Country nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, carriage house and barn. A country setting with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing 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.). NOTE: exempt from accepting service and emotional support animals.

Nagawicka Woods-Beautiful Lake Country Ranch Home

Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.

Scenic 4 Bedroom WI Lake Home - Newly Renovated!

Located just 30 mins west of Milwaukee lies this fabulous vacation lake home featuring 4 bedrooms, 2 full baths and unbelievable views of the lake throughout the home. Many popular restaurants and bars nearby, including “The Hideaway” right next door. Full lake and pier access, great for fishing and swimming. Nearby boat rental also available. 2 queen, 2 twin, and 1 king size bed along with two couches. The home has been recently renovated and feels like new. Free parking available.

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.

Historic Luxury |Walk to Downtown| King bed |Shops

✨ 1870s Elegance Meets Modern Comfort | Steps from Dining & Shopping ✨ Welcome to Downtown Delafield’s most charming and highly-rated historic stay! This stunningly restored 1870s apartment offers a luxury experience with vintage charm, all within walking distance to top-rated restaurants, boutique shops, and lakeside trails. Whether you’re visiting for a romantic escape, work trip, or weekend getaway, this unique property is designed to make your stay unforgettable.

Historic Downtown Gem| Walk to Dining, Shops, Lake

✨ 1870s Elegance Meets Modern Luxury ✨ Welcome to Downtown Delafield’s most sought-after Airbnb stay! This beautifully restored historic apartment offers a 5-star luxury experience with original 19th-century charm and modern amenities—all within walking distance to the best dining, shopping, and nature spots in the area. Bonus perk: this cozy gem is perched just above one of downtown’s favorite restaurants—so you’re literally steps away from an unforgettable meal.

Forest Bay Cottage

Lakefront Getaway on Okauchee Lake – Cozy Cottage with Stunning Views! Escape to the serene beauty of Okauchee Lake with this charming 2-bedroom, 1-bath cottage, in Wisconsin’s Lake Country. Whether you're seeking a quiet retreat or outdoor adventure, this vacation rental offers it all. Located just 30 minutes west of Milwaukee and 50 minutes from Madison, you’ll have easy access to some of the best lakeside activities in the area!