Holiday rentals in North Prairie

Custom Designer Home w/ Lake Views& Cozy Fireplace

💫Custom home centrally located in Pewaukee! It’s equipped with a gourmet kitchen, comfy Pottery Barn furniture, gas fireplace & stunning lake views. 📍You’re a quick walk to the shops, restaurants, activities and the beautiful Pewaukee Lake. 🏡🏡The home is part of another rental. With the layout, you will hardly hear other guests as there is minimal shared wall space and private entries. ⏩️Traveling with a larger group? You can also rent additional space at this home. Browse our host profile.

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!

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

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.

Tucked Away

For those in need of a "home away from home" while on the road working or just passing though on your travels. This private, quaint backyard parking/entrance mini apartment located in Waukesha's "Historic District" is for you. Enjoy large outer deck as weather permits. Stairs are required outside to enter unit. Walking distance to downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

Lakeside Getaway

Relax with the whole family at this peaceful, home on Lake Beulah. With the gorgeous lake and surrounding nature, you will feel you are hours up North, minus the long commute! Wake up and enjoy coffee on the deck. Bring your boat or grab a floaty and soak up the sun as you spend the day on the water. Wind down while you watch a stunning sunset from your own pier. Enjoy a show at the nearby Alpine Valley. Countless memories are just waiting to be made. Come play hard and relax even harder

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/ airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.* NOTE: No pets allowed.*

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.

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.

Cozy Cottage Lake Country

Welcome to our newly renovated two-bedroom cottage nestled in the heart of Lake Country! This cozy retreat boasts a living area with a fireplace, a fully equipped kitchen, a dining nook, a dedicated workspace, and modern amenities. Located conveniently between Milwaukee and Madison, you’ll find yourself surrounded by multiple lakes, hiking and biking trails, shopping, dining, festivals, and a plethora of other activities.