Cottage vacation rentals in Jackson

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Top-rated cottage rentals in Jackson

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Top guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 286 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

Cottage in Hartland

4.95 out of 5 average rating, 139 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.).

Top guest favorite

Cottage in Hustisford

5 out of 5 average rating, 66 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!

Top guest favorite

Cottage in Hartford

4.96 out of 5 average rating, 56 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 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.

Superhost

Cottage in Random Lake

4.84 out of 5 average rating, 68 reviews

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

Superhost

Cottage in Pewaukee

5 out of 5 average rating, 12 reviews

Lakeside Pewaukee Cottage

Get ready to enjoy this cozy, completely updated cottage. The property has neighborhood lake access to Pewaukee Lake just a short 5 minute walk away. Enjoy fishing off the piers, utilizing the provided kayaks or stand up paddle boards, or enjoying the sunset over the never-ending view of the Lake. Only a 25 minute drive to downtown Milwaukee! What better way to relax after a day on the lake than sitting in the 7 person hot tub or having a small fire in the backyard.

Top guest favorite

Cottage in Cedar Grove

5 out of 5 average rating, 35 reviews

Bright and Cheerful Lake Front Beach Cottage

Kick back and relax in this magical beach front cottage. Walk out the back door, and ten seconds later your toes are in the sand! Let all your worries just float off into the sunset. Whether you're into swimming and kayaking or cross-country skiing and snowshoeing, our cottage has it... all year round. Tucked away down a quaint private drive, yet only minutes from classic Supper Clubs and Boutique shopping in some of Wisconsin's most charming little towns.

Guest favorite

Cottage in Hustisford

4.97 out of 5 average rating, 116 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

Cottage in Hartford

4.98 out of 5 average rating, 43 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.

Top guest favorite

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

Cottage in Fond du Lac

4.88 out of 5 average rating, 107 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.