Holiday rentals in Sussex

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Top-rated holiday rentals in Sussex

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

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Top guest favourite

The exterior of a two-story home is visible, featuring large windows and a pleasant outdoor deck with shaded seating. A pergola is positioned nearby, surrounded by greenery and a stone pathway leading into the yard.

Home in Hubertus

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.

4.88 out of 5 average rating, 534 reviews

Top guest favourite

A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.

Guest house in Richfield

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.

4.95 out of 5 average rating, 306 reviews

Top guest favourite

A bright and open kitchen space features a large central island with dark cabinetry and a white countertop. Warm wood beams draw attention to the ceiling. A cozy living area with a gas fireplace is visible, along with large windows that frame views of the surrounding greenery.

Home in Pewaukee

Lakeview Retreat | Main + Guest House, Sleeps 10

Welcome to your ideal group retreat, 2 homes in 1, perfect for wedding groups, multi generational families & memorable getaways! Escape to our spacious main house + separate guest house for up to 10 guests with room to relax and connect while enjoying beautiful lake views & outdoor living space. We love our lake views, and while occasionally the train blows its horn, we provide white noise machines & earplugs. Check our host profile for additional homes if your preferred dates are unavailable

5.0 out of 5 average rating, 47 reviews

Top 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

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.

4.92 out of 5 average rating, 221 reviews

Top guest favourite

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.

Guest suite in Brookfield

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!

5.0 out of 5 average rating, 285 reviews

Guest favourite

Home in Waukesha

The Cozy Coop | Private Upstairs Retreat | Sleep 8

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - 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.

4.92 out of 5 average rating, 212 reviews

Guest favourite

A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.

Home in Oconomowoc

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

4.86 out of 5 average rating, 132 reviews

Top guest favourite

A spacious living area showcases a dark gray sectional sofa adorned with yellow and patterned cushions. A coffee table sits at the center on a patterned area rug, while a wall-mounted television is mounted nearby. Natural light enters through windows with a neutral-colored wall in the background.

Home in Delafield

Nagawicka Woods-Beautiful Lake Country Ranch Home

Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.

4.95 out of 5 average rating, 197 reviews

Top guest favourite

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.

4.96 out of 5 average rating, 348 reviews

Top guest favourite

A newly remodeled kitchen features wooden cabinetry and a dark countertop, paired with modern appliances. A large sink and a stovetop are highlighted, along with a window that provides a view of the outside. The flooring is made of warm wood, enhancing the overall design.

Home in Wauwatosa

Spacious Wauwatosa Home In Prime Location

We just finished remodeling the kitchen and all 3 bathrooms in our unique tri-level mid-century modern home. There are 4 bedrooms offering an array of accommodations as well as a couch with a pull-out queen bed. If you like to cook, our new kitchen is amazing! There is a fireplace room with a lovely view outside, a laundry room and a TV with cable, a DVR, and streaming apps like Netflix. WIFI is available. This is a quiet family neighborhood. No parties and please be respectful.

4.98 out of 5 average rating, 221 reviews

Top guest favourite

Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.

Guest suite in Sussex

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.

4.99 out of 5 average rating, 161 reviews

Guest favourite

A log cabin sits perched on a grassy embankment, framed by trees. The exterior features large windows and a spacious deck with steps leading down to the water's edge. Two red chairs are placed near the shoreline, reflecting the cabin's warm colors on the water.

Home in Nashotah

Okauchee Lakefront Cabin Escape

The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.

4.95 out of 5 average rating, 143 reviews