Vacation rentals in Town of Ashippun

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Stylish Retreat Near Wedding Venues + Fire Pit

Perfectly located for wedding weekends, lake getaways & downtown stays, this stylish home puts you minutes from top wedding venues, multiple lakes & Oconomowoc’s charming downtown while giving you space to relax & gather. Spend your days exploring nearby lakes, trails, & shops, then wind down with a glass of wine by the fire pit. Your furry friend is also welcome in on the fun- the Iron Ore is pet friendly! Traveling with a larger group? Check out our other area listings on our host profile.

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

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.

Rock River Retreat

Bring your family to make memories enjoying a movie while sitting by the fireplace. Enjoy fishing during the day and a beautiful Rock River View. During winter you are right near the Jefferson County Snowmobile trails: and during the spring these trails are used for ATVs. There are several bike trails in town as well. If you are looking for things to do try the Octagon House or the local antique stores, outlet malls When you are ready to dine, Wisconsin is known for it's many supper clubs.

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.

sauna and hot tub on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

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.

Firefly Cabin, a Unique Tranquil Space

Get ready for a relaxing getaway with your friends and family. Firefly Cabin has a lakehouse feel with all the comforts of home. This charming Cabin is only an hour drive from Milwaukee or Madison. It is the sister Cabin to Serenity Cottage, rent one or both! Please note Firefly Cabin does have stairs to main living area and areas of lower ceilings. This relaxing retreat won't disappoint and is a great option for a remote workers or a quick getaway from the city.

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.

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.