Cottage holiday rentals in Oshkosh

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Top-rated cottage rentals in Oshkosh

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Top guest favourite

Cottage in Oostburg

4.97 out of 5 average rating, 279 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 favourite

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 favourite

Cottage in Neshkoro

4.96 out of 5 average rating, 180 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 favourite

Cottage in Green Bay

4.92 out of 5 average rating, 115 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!

Superhost

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.

Superhost

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 favourite

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!

Superhost

Cottage in Union

4.87 out of 5 average rating, 47 reviews

Southern Door CountyWaterfront Cottage/Sunsets!

Relax and enjoy the stunning water of Green Bay in Southern Door County near Shoemaker Point.Sunsets to make memories, kayak or paddle board. Cottage living 20 mins to Sturgeon Bay, restaurants, farms, hiking, boating. Close to all Door County offers yet out of the hustle and bustle. New beds, well stocked kitchen and sweeping water views. Outdoor tables for dining and comfy outdoor covered patio with sofa and firepit. Close to Titletown for the NFL draft .permit #42-56-2812-00.

Guest favourite

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 favourite

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

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.

Top guest favourite

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.