Holiday houses in Waukesha

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Top-rated holiday rentals in Waukesha

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Top Guest favourite

Guest suite in Waukesha

4.97 out of 5 average rating, 30 reviews

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. Walking distance to lively downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital.

Top Guest favourite

Guest suite in Brookfield

5 out of 5 average rating, 234 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

Guest favourite

Home in Mount Mary

4.79 out of 5 average rating, 256 reviews

Private Milwaukee Home-Great Location, Entire Unit

This private upper level unit is only 3 miles from Froedtert Hospital, 1.1 miles from Mayfair Mall, and only steps away from Mount Mary University; bordering Wauwatosa, a suburb with great places to roam! This home is spacious, yet cozy. Offers a secure bedroom for 2, living room with a comfy sofa bed that sleeps one, dining area, bathroom, & full kitchen with all the necessities. A Key Less entry makes your check-in quick and easy! Minutes from the highway, making getting anywhere a breeze.

Top Guest favourite

Bungalow in Wauwatosa

4.97 out of 5 average rating, 226 reviews

Wauwatosa/Milwaukee “Inglewood Place”Classic Charm

Great location near all Milwaukee attractions and village of Wauwatosa.Cozy upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

Guest favourite

Cottage in Hartland

4.95 out of 5 average rating, 139 reviews

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.).

Superhost

Home in Waukesha

4.76 out of 5 average rating, 41 reviews

Modern Convenient 3BR W/ 2 King beds

Welcome to your Waukesha Retreat! Convenient location, welcoming clean space, relaxing backyard, and numerous amenities; this is the Airbnb for you. Here you will be minutes away from; American Family Field for your summer baseball games & concerts, downtown Milwaukee & the airport, diverse event halls, and the State Fairgrounds. Enjoy the luxury double shower and master suite as well as an outdoor private hot tub ready for guest use. Your home away from home! (Hot Tub closed Nov-Mid May)

Guest favourite

Townhouse in Waukesha

4.92 out of 5 average rating, 157 reviews

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.

Top Guest favourite

Home in Waukesha

4.93 out of 5 average rating, 40 reviews

Beautiful Home in Waukesha

What a wonderful location with a view from the front porch and a park in your back yard. Beautiful Brazilian Tiger wood floors in dining, living, and family room. Spacious family living area has an attractive gas fireplace as it's center point that is open to kitchen area. Off the dinette the three pane patio door has private woods view and patio area. Workout equipment in rec room. Minutes from lakes and hiking paths, Old Town Waukesha boutiques, and restaurants. Quick access to I-94

Guest favourite

Home in Pewaukee

5 out of 5 average rating, 8 reviews

Designer Home w/ Lake Views + Walk to Beachfront

💫This custom home is in the heart of Pewaukee! It’s equipped with a gourmet kitchen, comfy Pottery Barn furniture & stunning lake views. You’re a quick walk to the shops, restaurants, activities and the beautiful Pewaukee Lake. ⏩️Traveling with a larger group? You can also rent additional space at this home. Browse our host profile. 🏡🏡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.

Superhost

Cottage in Pewaukee

5 out of 5 average rating, 12 reviews

Lakeside Pewaukee Cottage

Get ready to enjoy this cozy, completely updated cottage. The property has neighborhood lake access to Pewaukee Lake just a short 5 minute walk away. Enjoy fishing off the piers, utilizing the provided kayaks or stand up paddle boards, or enjoying the sunset over the never-ending view of the Lake. Only a 25 minute drive to downtown Milwaukee! What better way to relax after a day on the lake than sitting in the 7 person hot tub or having a small fire in the backyard.

Guest favourite

Home in Waukesha

4.98 out of 5 average rating, 86 reviews

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.

Top Guest favourite

Guest suite in Helenville

4.95 out of 5 average rating, 366 reviews

Chic Loft Surrounded by Nature

This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

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Other great holiday rentals in Waukesha

Guest favourite

Private room in Greenfield

4.91 out of 5 average rating, 330 reviews

Spacious Downstairs Suite/private bathroom

KimberlyRating, 5 stars3 weeks ago

This is a wonderful basement space — living area with large screen tv, private bathroom with great shower, bed area is part of this open space. I used the coffee bar each morning and felt safe and comfortable. Most of the time I didn’t hear sounds from upstairs. I’d gladly stay here for future visits!

Top Guest favourite

Private room in New Berlin

4.99 out of 5 average rating, 259 reviews

The Orchard Room-Quiet Private Suite Near Milw

KaseyRating, 5 stars1 week ago

Staying here was awesome after spending the evening at the Brewers home game! We would definitely check this one out again!

Top Guest favourite

Private room in Menomonee Falls

4.95 out of 5 average rating, 101 reviews

Private space in quiet neighborhood

JenniferRating, 5 stars1 month ago

Emily’s place is comfortable, clean and welcoming. You can tell she’s thoughtful in the amenities she offers her guests and we enjoyed meeting her adorable cats too. Thank you, Emily!

Guest favourite

Private room in Waukesha

4.89 out of 5 average rating, 256 reviews

Cozy Room For Rent

RethaRating, 5 stars1 month ago

What a lovely stay and a wonderful host! Thank you so much for your hospitality.

Top Guest favourite

Private room in Racine

4.98 out of 5 average rating, 133 reviews

Cozy In Caledonia

AlekseyRating, 5 stars2 weeks ago

Great place to stay, because everything you would want

Top Guest favourite

Private room in South Milwaukee

4.95 out of 5 average rating, 346 reviews

Awesome Milwaukee location!

JimRating, 5 stars2 days ago

Mark is a gracious, friendly, and communicative host. The house is very clean. It even smells clean and fresh. Nice looking house and yard. Walkable to the lakeshore. Easily accessible to major roadways and public transportation. Would absolutely stay there again.

Superhost