Vacation rentals in Waukesha

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Top-rated vacation rentals in Waukesha

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in Brookfield

4.99 out of 5 average rating, 184 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax "in the Canopy" of beautiful maples! We’re a Superhosted, verified Guest Favorite, available for the GOP Convention! A comfortable retreat in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer. 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!

Sep. 16 – 23

$235 CAD per night

Guest favourite

Home in Wales

4.92 out of 5 average rating, 146 reviews

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

Jan. 16 – 23

$235 CAD per night

Guest favourite

Cottage in Hartland

4.96 out of 5 average rating, 113 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.).

Jun. 4 – 11

$216 CAD per night

Guest favourite

Home in Wauwatosa

4.98 out of 5 average rating, 178 reviews

Wauwatosa/Milwaukee 10 Minutes from Downtown

Great location near all Milwaukee attractions. Cozy upper two bedroom duplex with keyless entry in quiet Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular bars and restaurants 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 of WI. Near Am Fam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee. COME STAY WITH US!

Jan. 10 – 17

$225 CAD per night

Guest favourite

Guest suite in Sussex

4.96 out of 5 average rating, 240 reviews

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.

Jan. 31 – Feb. 7

$153 CAD per night

Guest favourite

Apartment in Wauwatosa

4.83 out of 5 average rating, 263 reviews

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Sep. 17 – 24

$128 CAD per night

Guest favourite

Guest suite in Brookfield

4.88 out of 5 average rating, 107 reviews

Family Friendly - Entire Guest suite

The lower level of our single family home is perfect for families of all kinds . It will give you all the comforts of home, including a spacious backyard, free parking, full-size kitchen, trampoline, fire pit, and a basketball hoop! Our home is 10 mins or less from: the Milwaukee County Zoo, Am Fam Field, STATE FAIR PARK; 15-25 min to downtown, Lake Michigan, numerous inland lakes including Pewaukee; 20 mins to airport; 35 mins to Alpine Valley & 15 MINS TO SUMMERFEST!

Aug. 9 – 16

$198 CAD per night

Guest favourite

Apartment in West Allis

4.91 out of 5 average rating, 255 reviews

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Sep. 25 – Oct. 2

$185 CAD per night

Guest favourite

Home in Muskego

4.98 out of 5 average rating, 142 reviews

3 Bedroom Muskego Home

Be our guest in a Country like 1,800 sq ft home nestled in a wetlands setting with a 1 car garage. Sleeps 6 in a master suite and 2 smaller bedrooms. Home has 2 full bathrooms with 2 showers. Full kitchen with a refrigerator and a dishwasher. Has a Laundry room with washer and dryer. A gas stone fireplace graces the family room. A Large deck is out back with an outdoor gas grill. Also, a 220 Volt EV charger is available for your use

Feb. 14 – 21

$250 CAD per night

Guest favourite

Apartment in Elkhorn

4.95 out of 5 average rating, 330 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

Apr. 8 – 15

$147 CAD per night

Guest favourite

Home in West Allis

4.97 out of 5 average rating, 161 reviews

Near to all Milwaukee favorites/ Free Parking/WiFi

Make yourself, family or friends at home in this Cozy comfortable upper 2 bedroom, 1 bathroom house with Wisconsin charm! It’s a great location in the city of West Allis just a short drive to everywhere in Milwaukee. I appreciate that you considered my Airbnb listing! Please feel free to contact me on how I can improve your stay. Also, please take a moment to review my house rules. Can wait to host you, thanks!!!

Jan. 19 – 26

$156 CAD per night

Guest favourite

Cabin in Kenosha

4.81 out of 5 average rating, 539 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Oct. 21 – 28

$183 CAD per night