Cottage vacation rentals in Lake Winnebago

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Top-rated cottage rentals in Lake Winnebago

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Top guest favorite

The exterior of the cottage is surrounded by lush greenery, showcasing a wooden deck with comfortable seating. A grill is positioned nearby, while a neatly manicured lawn provides an inviting outdoor space, perfect for relaxation in a serene woodland setting.

Cottage in Oostburg

4.97 out of 5 average rating, 281 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 private dock extends over calm waters, accompanied by two bright yellow kayaks secured along the wooden landing. A ladder is visible, providing access to the river, while barren trees line the distant riverbank, contributing to a serene natural setting.

Cottage in Princeton

4.97 out of 5 average rating, 194 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?

Guest favorite

A serene lakeside scene is depicted, featuring four blue Adirondack chairs arranged around a fire pit on a grassy area. In the background, a wooden dock extends over the calm water, with trees lining the shore, contributing to a tranquil atmosphere.

Cottage in Neshkoro

4.96 out of 5 average rating, 181 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!

Superhost

Two light-colored chairs are positioned beside a small wooden table, offering a cozy seating area. A large window provides a view of the lake and trees, creating a bright and airy atmosphere. Soft natural light filters in, enhancing the space.

Cottage in Waupaca

5 out of 5 average rating, 3 reviews

Lake Cottage with Sunset Views!

Steps from the sandy shore-line, spring fed crystal clear water, on Stratton Lake. Enjoy fishing, swimming, and boating during the day with sunset views and campfires at night. Kayaks, paddleboards, paddle boat, and swim raft are available for use or bring your own boat and tie off on the dock. Minutes from shops, entertainment, attractions, restaurants and the Chain O' Lakes. The perfect location for your lakeside get-away! Note: Host may ask for ID verification related to compliance.

Top guest favorite

A charming stone structure stands beside a vibrant lakeside landscape, framed by tall trees displaying autumn foliage. The sky showcases a blend of colors during sunset, reflecting on the serene water in the background.

Cottage in Hustisford

5 out of 5 average rating, 63 reviews

Charming Lakeside Cottage

Don't waste your weekend driving when Serenity Cottage is only an hour from Milwaukee or Madison. This charming lakehouse has beautiful views and a private island. Both the cottage frontage and island have firepits. 2 kayaks, 2 paddle boards, and a pedal 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. Serenity awaits!

Superhost

A cozy living area features a pair of sofas with decorative pillows, arranged around a round wooden coffee table. A light fixture and patterned area rug add character, while a doorway leads towards the kitchen, providing a glimpse of the open layout.

Cottage in Wild Rose

5 out of 5 average rating, 3 reviews

Water's Edge Cottage @ Evergreen Campsites&Resort

Welcome to Waters Edge where you will feel right at home in this bright contemporary home! Our spacious home and the best deck in the resort will be sure to delight your family and friends. This pet free cottage features 2 bedrooms and 1 spacious bathroom perfect for your family getaway in any season. During the summer months you will be able to use all the resort's amenities and during the winter cozy up next to the fireplace after spending the day at the local ski and tubing hill.

Guest favorite

A charming yellow cottage is surrounded by towering pine trees within a spacious yard. Sunlight filters through the branches, illuminating the greenery. The area offers a peaceful setting, providing an inviting space for relaxation and outdoor activities.

Cottage in Wautoma

4.85 out of 5 average rating, 40 reviews

TOWERING PINES! Charming 2 bedroom cottage WAUTOMA

This charming cottage is nestled between beautiful Irogami and Silver Lake. Centrally located within walking distance of the locally famous Silvercryst supper club. You can feel the tranquility as soon as you step outside into the 1/2 acre yard. A short walk from two boat launches on Irogami. This is the perfect get away location with golf courses, parks, supper clubs, fishing, & shopping nearby. Our cottage is a comfortable stay in a central location. A great getaway spot for all!

Guest favorite

The exterior of the schoolhouse displays a charming dark wood façade, complemented by a light purple front door. Two blue Adirondack chairs are positioned on the lawn, inviting relaxation under the clear sky. The property is surrounded by well-kept grass and trees.

Cottage in Neshkoro

4.95 out of 5 average rating, 138 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.

Guest favorite

An open front door leads to a view of the calm lake, framed by trees. A grassy path extends towards the water's edge, with a glimpse of the neighboring structures visible in the distance.

Cottage in Pardeeville

4.9 out of 5 average rating, 155 reviews

Lake View Retreat

A perfect spot to escape! Just a short stroll to Park Lake with stunning sunsets. Our cozy cottage/lake view is just what you need to relax and unwind after the day's adventures. A stocked kitchen/LR with coffee, games, DVD player, DVD'S, 40” smartTV. Prime location to all things fun! Lake activities, hiking, exploring in the summer and ice fishing, downhill skiing and snowmobiling in the winter! We love sharing our space and know you will love it just as much.

Superhost

The enclosed porch features large windows allowing natural light to fill the space. A hammock hangs invitingly alongside a tile floor. A dining table and chairs are positioned in one corner, providing a cozy spot to enjoy meals or relax.

Cottage in Markesan

4.81 out of 5 average rating, 102 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.

Guest favorite

A charming cottage is located near the water's edge, framed by lush green grass and a few trees. Outdoor equipment, including kayaks and a table setup for dining, adds convenience for guests. The exterior is painted in a soft blue, enhancing its inviting appearance.

Cottage in Hustisford

4.96 out of 5 average rating, 114 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

An outdoor seating area features a hanging chair and a cozy couch, facing a fire pit with flames visible. The setting transitions from warm sunset hues to deep blue in the sky, while the calm waters of Lake Winnebago reflect the evening light.

Cottage in Fond du Lac

4.99 out of 5 average rating, 282 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.