Holiday houses in North Prairie

Willow Springs Loft @ Wern Valley

Looking for that beautiful once in a lifetime opportunity to sleep in the hay loft? Look no further. No expense has been spared in the space. It is beyond beautiful with every rustic feel you can think of, yet extremely classy. Railings made from cattle stanchions, shower heads that are watering cans and sinks from wash tubs. The evening view of deer and turkeys in the valley from your 30 foot deck is priceless. Ride your ATV to Wern Valley Sportsmen’s Club for a pheasant hunt or clays shooting.

Value · Location · Check-in

Modern Lake Country Farmhouse in Delafield

Just a half mile outside downtown Delafield, this charming, modern farmhouse is clean, updated and well stocked. There's plenty of space to have a peaceful, relaxing stay. Easy access to golf, lakes (like Nagawicka and Upper & Lower Nemahbin), parks (like Lapham Peak State Park), hiking, biking and x-country skiing. Enjoy walking access to restaurants and shops in Delafield. Just minutes off I-94 in Lake Country, conveniently located between Milwaukee and Madison. 30 minutes from Fiserv Forum.

Value · Location · Condition

Lake House Retreat on Phantom Lake

A cozy secluded retreat like being "up North" without having to go up North. Quiet private road, and quiet lake. Great swimming and fishing off the dock in this sandy bottom lake with clean spring fed water, and large grassy area for lawn games and relaxing. Great for families, ladies retreats, golf groups, or concert goers. Only 5 mins to grocery stores. Lots of space in the house, and lots of space for spending time outside on the deck or the dock or lawn by the lake. Feel free to inquire!

Family · Location · Accuracy

The Cozy Coop | Private Upstairs Retreat | Sleep 8

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - 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.

Value · Location · Parking

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.

Family · Location · Hospitality

The Retreat: 5 Acre Log Cabin

Escape to this beautiful 5-acre country retreat, located a short drive from Lauderdale Lakes, Alpine Valley, and Lake Geneva. The cabin features two kitchens, two family rooms, a year around outdoor hot tub, a game room, and five bedrooms with comfortable king-sized beds. The master suite also includes a steam room for added luxury. Spend your days enjoying the great outdoors with a game of beach volleyball or roasting marshmallows around a bonfire, while taking in the fresh midwestern air.

Location · Value · Cleanliness

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.

Value · Location · Walkability

Lake Country Retreat| Shared Pier Access|Lake View

Just steps from the shores of Lake Nagawicka, this cozy home offers the perfect blend of relaxation and adventure. Enjoy a shared pier for kayaking, paddleboarding, or lakeside lounging. Minutes from downtown Delafield and endless activities. Rent from our preferred boat partner or bring your own, boat slip available for minimal cost. Ideal for couples or small families. Whether you’re looking to unwind, explore, or make lasting memories by the water, this inviting getaway has it all.

Family · Location · Checkout

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.

Family · Location · View

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.

Family · Value · Access

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Location · Family · Accuracy

A-Frame in forest on bike trail!

Classic A-Frame, in the woods. Borders the Kettle Moraine State Forest on 3 sides. Exterior: 2 acres, fully-fenced and dog-friendly. Hop on the "Connector" mountain bike trail right out the backyard. Or take a hike on the nearby Ice Age trail, Bald Bluff, John Muir, Nordic, or snowmobile trails. Interior: 1,500 square feet, 2 levels, open concept main living area with loft ceiling, wood-burning fireplace, 2 arcade machines, outdoor firepit, frisbee golf stand, etc.

Family · Value · Layout