Cottage vacation rentals in Lake Winnebago

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Top-rated cottage rentals in Lake Winnebago

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Top guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 290 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.

Guest favorite

A rocky ledge is observed with a view of rolling hills and valleys under a partly cloudy sky. A child wearing a baseball cap is positioned to the side, gazing thoughtfully into the expansive landscape, framed by scattered trees and natural rock formations.

Cottage in Poynette

4.96 out of 5 average rating, 230 reviews

Lake Wiscosnin Cozy Cottage

Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi

Guest favorite

The living area features a light-colored sofa paired with two armchairs, accompanied by a small table. A decorative rug adds warmth to the hardwood floor. Natural light streams in through large windows, offering views of the surrounding trees.

Cottage in Princeton

4.97 out of 5 average rating, 202 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Top guest favorite

A Cedar soaking hot tub emits steam, inviting relaxation. Natural wood surrounds the tub, complemented by greenery nearby. A bench offers additional seating, while decorative wall hangings add a touch of charm. Soft lighting enhances the calming atmosphere of the outdoor space.

Cottage in Two Rivers

4.99 out of 5 average rating, 103 reviews

Cedar Soaking Hot Tub~King BED~No Cleaning Fee

*No Cleaning Fees added to end cost! 🤗 Licensed by County. Welcome to Sandy Bay LakeHouse. Listen to the waves of Lake MI~2 blocks away~in this newly built 2BR/1BA cottage (2023). The home is conveniently located within walking distance of Neshotah Beach/Park (2 blocks). Ice Age Trail access right across street. Walsh Field across street. Outdoor Cedar Soaking Hot Tub,along with Lava Firetop table & quality outdoor furniture ensures your time at Sandy Bay Lake House is relaxing & memorable

Guest favorite

A peaceful lakeside view features a private dock extending over the calm water, shaded by willow trees. Lounge chairs are arranged on the grassy shore, offering a relaxing spot for enjoying the scenery. A turquoise kayak rests nearby, adding to the tranquil setting.

Cottage in Neshkoro

4.95 out of 5 average rating, 193 reviews

Nostalgic Lakehouse with Ferry Pontoon & Hot Tub

This thoughtfully restored 1960s cottage sits on peaceful Spring Lake: perfect for swimming, fishing, and creating nostalgic memories lake with your family. Outside you'll enjoy a beautiful private backyard with a hot tub, paddle/solar-powered pontoon boat, yard games, fire pit, fishing poles, and dock. Inside you'll make lifelong nostalgic memories with the huge selection of 1980/90s video games, Goosebumps books, board games & VHS films. Centrally located in an activity-filled area of WI!

Guest favorite

The viewing tower features large windows that provide a panoramic view of the bay and surrounding greenery. Soft lighting is created by decorative lanterns along the ceiling. A cozy ottoman sits on the wooden floor, complementing the warm wooden walls.

Cottage in Green Bay

4.92 out of 5 average rating, 118 reviews

⌈W a t e r f r o n t ⌋ cottage with tower!

This charming cottage is an ideal respite for your family holiday to the one-of-a-kind Green Bay, Wisconsin! Look forward to exploring this historic city, visiting iconic museums, and experiencing the vibrant Packers culture. The vacation rental home sits right on the water - offering fantastic views of the bay - and is just 10 miles from downtown. After the day's adventures, return to this cozy 3-bed, 1.5-bath house and unwind, as your furry friends or children play in the waterfront yard!

Guest favorite

The exterior of a black schoolhouse is framed by snow-covered evergreen branches. A pale purple door stands out against the dark siding, while snow blankets the ground and rooftops, creating a serene winter landscape.

Cottage in Neshkoro

4.95 out of 5 average rating, 139 reviews

Pet Friendly Antique Schoolhouse with Fenced Yard

Pond Lily is truly a unique stay; a historic schoolhouse among tranquil surroundings. Beautiful traditional craftsmanship meets all the comforts of a modern home. Pet friendly with a fenced yard. A well-stocked kitchen makes for easy home-cooked meals. The layout is ideal for small groups looking to enjoy a peaceful getaway. Snuggle up by the wood-burning fireplace in the cold months or enjoy the firepit in the warm weather. For the outdoorsman, public lands are 5 minutes away.

Superhost

Two green chairs are positioned near a crackling fire pit surrounded by fallen leaves, overlooking a pond. Soft evening light casts a warm glow, while trees provide a natural backdrop, creating a peaceful outdoor space for relaxation.

Cottage in Markesan

4.81 out of 5 average rating, 104 reviews

Cottage on the Pond - Big Green Lake

Our place is good for couples, solo adventurers, families, and furry friends (dogs limit 2 $50 fee). Enjoy the peace and beauty of the pond (sorry, no fishing) while just across the street from beautiful Green Lake. Lots of room outside for the kids to roam. Easy walk to the beach. (see satellite map picture). There is a public launch nearby and plenty of room to keep your boat on the side lawn. Hiking trails, White River Marsh, and Fox River are all nearby.

Top guest favorite

A fire pit is filled with bright flames, surrounded by a stone patio. The lake reflects the warm colors of twilight, with a pier and boats visible in the background. Soft greenery frames the scene, enhancing the tranquil outdoor setting.

Cottage in Hustisford

4.96 out of 5 average rating, 119 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.

Top guest favorite

A view of a fire pit featuring a gentle flame against a serene lake backdrop at dusk. The horizon displays soft gradients of orange and blue. Silhouettes of adirondack chairs and a boat dock can be seen in the distance, enhancing the tranquil atmosphere.

Cottage in Fond du Lac

4.99 out of 5 average rating, 287 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Top guest favorite

Cottage in Fond du Lac

4.93 out of 5 average rating, 134 reviews

The Beach House

Cute year round home with fantastic evening sunsets on the East shore of Lake Winnebago. Enjoy the lake life with this 3 bedroom, 1.5 bath, private beach and pier, located on a private beach road and a close drive to restaurants in the surrounding area. Ideal for Walleye Weekend, EAA Convention, Road America, Green Bay Packer games, Wisconsin Badger games, Milwaukee Brewer games, Ryder Cup and more

Guest favorite

A collection of tableware is displayed on a rustic shelf. The assortment includes plates with a floral design and various cups, arranged carefully. A mix of ceramic and metal items adds visual interest, while the background features a soft green wall, creating a calming environment.

Cottage in Fond du Lac

4.88 out of 5 average rating, 108 reviews

Milk House Cottage

Once a small barn, now a unique guest house surrounded by trees and nature. A secluded setting, yet right on the edge of the city and in close proximity to three colleges. Not far to Fond du Lac Loop bike and walking trail. Also close to grocery stores and great restaurants. Explore the nature area on the property! Out of consideration of all guests NO pets are allowed.