Vacation rentals in Waukesha

4.99 out of 5 average rating, 142 reviews

The modern farmhouse is viewed from a distance, showcasing its clean white exterior and well-maintained landscaping. A paved driveway leads to the entrance, flanked by neatly trimmed bushes and vibrant green grass, creating an inviting approach to the home.

Home in Delafield

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.

4.95 out of 5 average rating, 142 reviews

The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.

Home in Menomonee Falls

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Guest suite in Brookfield

A two-story home is surrounded by vibrant autumn foliage, featuring large trees displaying rich yellow and orange leaves. A gravel driveway leads up to the house, with fallen leaves carpeting the ground. A garage is visible in the background, adding to the serene neighborhood setting.

5 out of 5 average rating, 240 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!

4.97 out of 5 average rating, 233 reviews

The exterior of a two-story brick duplex is shown, featuring a welcoming entrance. Lush green lawns are bordered by manicured flower beds. Steps lead to the front door, flanked by hanging flower baskets and illuminated by wall-mounted lanterns. A concrete pathway curves gently through the yard.

Bungalow in Wauwatosa

Wauwatosa/MKE “Inglewood Place” Historic 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.

4.95 out of 5 average rating, 145 reviews

A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.

Cottage in Hartland

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.).

4.92 out of 5 average rating, 167 reviews

The open kitchen features modern appliances, including a dishwasher and sink with a spacious countertop. Natural light fills the adjoining living area, which is equipped with a large smart TV and comfortable seating, creating an inviting space for relaxation.

Townhouse in Waukesha

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.

4.95 out of 5 average rating, 128 reviews

The historic home, designed in a Queen Anne Victorian style, features a white exterior with intricate woodwork. Large windows reflect soft evening light, while a spacious porch offers a welcoming entry. The surrounding yard is open, with mature trees that provide shade and a natural ambiance.

Home in Wales

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

4.96 out of 5 average rating, 297 reviews

A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.

Guest suite in Sussex

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.

4.89 out of 5 average rating, 232 reviews

A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.

Guesthouse in Racine

Charming log cabin in the woods

This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

Guest suite in Germantown

A quaint two-story building is set amidst a well-maintained green lawn, surrounded by mature trees. A gravel driveway leads to the side of the structure, with additional buildings visible in the background, contributing to a peaceful rural ambiance.

4.92 out of 5 average rating, 142 reviews

1853 Farmhouse Apartment

Welcome to a two-bedroom apartment. The space includes a private bathroom, kitchen and living area. There is no kitchen/dining table. The apartment is on the second floor of the house and has an outside staircase leading up to it. The entrance/staircase is not shared by the hosts and there are no shared spaces in the home. The staircase may be steep for persons who have difficulty navigating stairs. Guests are welcome to use the patio area on the property.

4.95 out of 5 average rating, 416 reviews

A vibrant scene of a countryside farm is depicted, featuring a red barn and a silo in the background. Lush green grass and trees frame the image, while a fenced area adds a rustic touch, completing the serene rural landscape.

Apartment in Elkhorn

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!

Guest suite in Helenville

The spacious loft features a modern open layout, with a kitchen area showcasing white cabinetry and a large granite countertop. Natural light floods the space through multiple windows, highlighting a cozy seating area beside a fireplace and a unique handcrafted couch that doubles as a bed.

4.95 out of 5 average rating, 369 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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Popular amenities for Waukesha places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Waukesha

Superhost

A flat-screen television is positioned on a sleek black stand, with a light-colored wall behind it. The area is softly illuminated, and a fireplace can be seen in the background, adding to the comfortable living space.

4.88 out of 5 average rating, 60 reviews

Cozy 3BR Ranch Home Away From Home

5 out of 5 average rating, 9 reviews

A serene waterfront view showcases a calm lake under a clear blue sky. A fire pit is placed on a stone patio, surrounded by several white adirondack chairs. A private pier extends into the water, providing a clear line of sight across the lake.

Home in Pewaukee

Waterfront on Pewaukee Lake |3BR/2BA|Paddle Boards

5 out of 5 average rating, 10 reviews

The living area features a spacious light-colored sectional sofa paired with a warm leather armchair. A cozy gas fireplace is framed by a stone wall, and large French doors allow natural light to fill the space while providing access to the outdoor area.

Home in Pewaukee

Designer Home w/ Lake Views + Walk to Beachfront

5 out of 5 average rating, 63 reviews

An open-concept living area showcases contemporary design elements. A cozy seating area is complemented by a large sectional sofa. Bright yellow chairs surround a dining table, while modern lighting fixtures and unique wall art add character to the space. Large windows provide ample natural light.

Cabin in Pewaukee

Pewaukee Serenity Cottage: Whimisical by the Lake

4.93 out of 5 average rating, 30 reviews

The exterior of a renovated farmhouse features a covered porch with large windows, allowing for natural light. A well-maintained lawn and garden area are present, with a stone pathway leading to the entrance. The house showcases a combination of white siding and dark trim.

Home in Pewaukee

Bougie by the Beach

The exterior of a spacious home is displayed, showcasing a well-maintained lawn with seasonal foliage. A covered entrance is flanked by windows, and decorative plants are positioned at the base of the house. The facade features sleek horizontal siding and contrasting blue shutters.

4.94 out of 5 average rating, 47 reviews

Beautiful Home in Waukesha

A cozy studio space features a spacious bed with soft linens, a light-colored coffee table, and a modern gray couch adorned with decorative pillows. Two wall art pieces are displayed above the couch, and a large mirror reflects the inviting atmosphere.

4.97 out of 5 average rating, 92 reviews

Brand New Studio w. Private Entry + Garden Patio

Superhost

A modern kitchen features dark wood cabinetry and a large central island with seating for two. Stainless steel appliances include a refrigerator and oven, while turquoise tile backsplashes add a pop of color. Natural light fills the space through nearby glass doors.