Cottage vacation rentals in Sussex

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Top-rated cottage rentals in Sussex

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Guest favorite

Cottage in Richfield

4.95 out of 5 average rating, 238 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.

Nov 22 – 29

G$37,667 GYD per night

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 235 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Mar 1 – 8

G$31,689 GYD per night

Guest favorite

Cottage in Hartford

4.95 out of 5 average rating, 40 reviews

The Lazy Dais Cottage on Pike Lake.

Relax with the whole family, including pets, at this newly renovated three-bedroom lake cottage. Included with your stay - your own pier for your boat, 2 kayaks, 2 paddle boards, a paddle boat, a swim mat, and floaties. Pike Lake is a full recreational lake with a State Park covering half making it a peaceful, beautiful setting. Sit by the water and have a fire under a blanket of stars at night. Enjoy a peaceful morning cup of coffee on the front porch while viewing this truly gorgeous lake.

Jan 3 – 10

G$48,231 GYD per night

Guest favorite

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 26 – Jul 3

G$30,048 GYD per night

Superhost

Cottage in Elkhorn

4.78 out of 5 average rating, 129 reviews

Connie's Cottage on the Lake.

Enjoy our charming lake house retreat; wake up peacefully to a beautiful view of North Lake and all its wildlife. Enjoy a cup of coffee on the screened in porch before heading out to kayak, fish, or explore. Grill out and listen to music before ending the day with a cocktail by the bonfire. The cottage has central air/heating and is a perfect place for family and friends. There is a sofa bed in the game room that sleeps 2. There is parking for 3 cars. Discounts avail for 7 or 30 day stays.

Mar 30 – Apr 6

G$49,511 GYD per night

Guest favorite

Cottage in Delafield

5.0 out of 5 average rating, 41 reviews

Lake Country Guest Cottage

This property is tucked away and feels like you’re in the Northwoods or at your own private resort, yet is so close to it all. It is truly a recreation haven due to the proximity of lakes and rivers, as well as State and county parks. Choose from many amazing restaurants downtown, within a mile drive or 15 minute walk (trail/road), or stay in to cook at home/barbecue on the gas grill. *10’ of the yard, near the back fence, will be used for landscaping on nextdoor property (mid Aug-Sept)

Apr 22 – 29

G$59,905 GYD per night

Guest favorite

Cottage in Hustisford

5.0 out of 5 average rating, 41 reviews

Charming Lakeside Cottage

Don't waste your weekend driving when Serenity Cottage on Lake Sinissippi is only an hour from Milwaukee or Madison. Our charming lakehouse has beautiful views and it's own private island. Both the cottage frontage and island have firepits. 2 kayaks and a paddle boat are included in the rental. This property is a 4 minute walk from the Sinissippi Lake Pub which has indoor and outdoor seating. Downtown Hustisford is only a 2 minute drive and offers restaurants and shops.

Dec 19 – 26

G$43,145 GYD per night

Guest favorite

Cottage in Fox Lake

4.85 out of 5 average rating, 285 reviews

The Little White Cabin, Fox Lake WI

****As of October 15, 2023, all of the piers are out of the water for the winter season.**** This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!

Feb 23 – Mar 2

G$27,774 GYD per night

Guest favorite

Cottage in Beaver Dam

4.95 out of 5 average rating, 21 reviews

Cozy lakeside getaway

Relax at this peaceful lakeside cottage. Launch your canoe or kayak at the private dock (May to Sept) or your power boat at the nearby county park, prepare food in the kitchen, lounge on the three-season porch, and build a fire in the evening. This 1950s fishing cottage has been updated with modern amenities. Only an hour from Madison or Milwaukee, you'll feel stress fall away in the gentle lake atmosphere. Treat yourself to a few days at Stillwater Cottage!

Dec 27 – Jan 3

G$36,433 GYD per night

Guest favorite

Cottage in Hustisford

4.99 out of 5 average rating, 91 reviews

Charming and Cozy Cottage on Lake Sinissippi!

Pine Shore Retreat is a charming cottage so close to the lake that you feel like you are in a houseboat! The east side location means you have fabulous sunset views, as well as swimmable, hard bottom frontage off the platform pier. It is a small space, just one bedroom, but very cozy. Comfort is the focus, with new, high-end furnishings. The stainless steel refrigerator, granite countertops and a gas range in the kitchen offer a higher end experience.

Aug 11 – 18

G$42,237 GYD per night

Guest favorite

Cottage in Hartford

4.97 out of 5 average rating, 31 reviews

Cheerful cottage in the middle of the Kettles.

Welcome to the "Middle House", where you're minutes from civilization yet you feel in the middle of nowhere. Step out the front door and hop on the Ice Age Trail, head south to Holy Hill and explore the Basilica or head north to Pike Lake State Park and enjoy the beach just minutes from the front door. This 2 bedroom fully remodeled cabin is warm and inviting, a great place to relax after your adventures in the "Middle" of the Kettle Moraine Forest.

Dec 17 – 24

G$36,088 GYD per night

Guest favorite

Cottage in Kansasville

4.94 out of 5 average rating, 115 reviews

The Oasis Lake House

This charming Eagle Lake cottage is just steps from the water, so you can enjoy the beautiful views of the lake from inside the house, the back deck, paddling the 2 kayaks and paddleboard, the sandy beach or adirondack chairs. A great place to come and soak in the quiet, play a competitive game of bags and a fisherman's paradise, all will enjoy the beauty and evening conversations around a roaring fire or cozied up in the cottage.

Jan 8 – 15

G$61,287 GYD per night