Holiday rentals in Germantown

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Top-rated holiday rentals in Germantown

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

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Top guest favourite
A wooden gazebo features two comfortably arranged chairs with blue cushions and a small table, overlooking a serene pond and lush greenery. A patio heater stands centrally, adding warmth to the outdoor space, which is framed by trees and walking paths.
Guest house in West Bend
5 out of 5 average rating, 98 reviews

Wilderness Retreat*Private Deck*Gazebo*Fireplace

Wilderness Retreat getaway with scenic views in the country. Minutes to downtown West Bend & a short drive to Historic Cedarburg! Private deck overlooking pond & gardens. 4 acres w/walking paths to enjoy nature & bird watching. Cozy amenities include gas fireplace, heated bathroom floor & patio fireplace in gazebo! You'll find peace & relaxation at our countryside retreat w/all the comforts of home. Complimentary Netflix. High speed internet, perfect for working remotely. Extended stays welcome!

Top guest favourite
A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.
Guest house in Richfield
4.95 out of 5 average rating, 296 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Top guest favourite
A cozy living area features a large brown sectional sofa adorned with patterned cushions. Windows allow natural light to flood in, showcasing views of the outdoors. A round wall clock hangs above, and a small wooden bench complements the inviting space.
Flat in Cedarburg
5 out of 5 average rating, 94 reviews

Perfect Balance in Cedarburg Gem

This spacious, private studio apartment offers a perfect blend of serenity and activity. Situated at the back of a 1.25 acre lot, beyond the lovely 1862 stone farmhouse it overlooks, the carriage house is a peaceful getaway -- minutes from all that bustling historic Cedarburg has to offer. Just .4 mile from the OZA Fairgrounds and .8 mile to downtown shops and restaurants, it's a quick drive or an easy walk to many amenities. Relax on the balcony before or after a day of fun sightseeing. Cheers!

Guest favourite
Home in Waukesha
4.93 out of 5 average rating, 197 reviews

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - 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.

Top guest favourite
A serene lakeside setting features two black Adirondack chairs positioned around a small table, surrounded by lush green grass. In the background, gentle ripples of the lake and trees provide a peaceful atmosphere, while kayaks rest nearby, inviting leisurely exploration.
Home in Hubertus
4.88 out of 5 average rating, 521 reviews

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

Top guest favourite
An outdoor seating area is showcased on a wraparound deck, featuring a sectional sofa with neutral cushions and a coffee table. A scenic view of wetlands and greenery is visible in the background, creating a serene environment for relaxation.
Barn in Cedarburg
4.97 out of 5 average rating, 204 reviews

Big Red Barn with a basketball court

A beautifully transformed dairybarn turned into a rustic Lodge with all the accommodations. Enjoy a full kitchen and bar filled with a gas fireplace, dart board and pool table. Head upstairs to the basketball court and onto a wraparound deck that over looks acres of wetlands with wildlife A birdwatchers paradise. If you need to detox we have a wood-burning sauna with all the wood and kindling for you to enjoy. We are located 2miles outside historic Cedarburg Wi and 25 minutes north of Milwaukee.

Guest favourite
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
4.93 out of 5 average rating, 201 reviews

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.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 261 reviews

sauna and hot tub on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Top guest favourite
A well-equipped kitchenette is shown, featuring a stainless steel refrigerator, microwave, and a coffee maker. Above the countertop, mugs are neatly arranged on a hanging rack. A glass-paned door leads to another room, adding a touch of elegance with a chandelier visible through the glass.
Guest suite in Sussex
4.96 out of 5 average rating, 334 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.

Top guest favourite
Guest suite in Sussex
4.99 out of 5 average rating, 153 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Guest favourite
An outdoor patio area is depicted, featuring a set of gray lounge chairs surrounding a wooden table. A black barbecue grill is positioned against the vibrant orange wall, with greenery visible in the background. Large windows provide a view into the interior space.
Townhouse in Thiensville
5 out of 5 average rating, 8 reviews

500 House - Unit C

 Welcome to your modern retreat in a sustainably built property that blends comfort, style, and convenience. This thoughtfully designed unit offers a bright open floor plan, private patio, and access to beautifully shared community spaces—including a fire pit and outdoor lounge area. Whether you're here for a solo getaway, a family vacation, or a group gathering, the 500 House provides the perfect balance of privacy and connection.  Relax, explore, and feel right at home.

Top guest favourite
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.
Guest suite in Germantown
4.93 out of 5 average rating, 162 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.

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