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Cottage vacation rentals in Madison

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Top-rated cottage rentals in Madison

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite
A cottage is nestled within a wooded area, featuring light-colored siding and a green roof. A wooden deck leads to the entrance, surrounded by autumn leaves and natural landscaping. Windows allow natural light to illuminate the interior, creating a warm and welcoming exterior.
Cottage in Poynette
4.96 out of 5 average rating, 249 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

Superhost
A charming white cottage is surrounded by greenery, featuring a sloped roof and a prominent red chimney. A covered porch with white railings offers a welcoming entrance, while large windows allow natural light to fill the interior.
Cottage in Arena
4.89 out of 5 average rating, 307 reviews

Sugarland Cottage

The Sugarland cottage is designed to accommodate up to 8 guests. It has a full kitchen, bathroom with shower, two bedrooms, one with a queen bed and the other with a double and 2 twin beds. Downstairs is a pull out queen sized Murphy bed. Situated in a major southern Wisconsin tourism area, Sugarland cottage is close to the Wisconsin River and only 30 minutes from Madison and 10 minutes from Spring Green home of Frank Lloyd Wright’s Taliesin, American Player’s Theater, and House on the Rock.

Top guest favorite
A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.
Cottage in Hartland
4.96 out of 5 average rating, 158 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.).

Guest favorite
Cottage in Edgerton
4.86 out of 5 average rating, 160 reviews

Rock River Rest, river cottage close to Madison!

Escape the city to our 1920s vintage riverside cottage. Nestled among centuries old Oaks, enjoy your own private sanctuary with over 100 feet of waterfront. Relax with a bonfire under the stars, sip coffee watching wildlife up close or unwind after a day kayaking from our waterfront. Perfect for couples, travelers, or business persons -- come and enjoy the scenic countryside, all with the convenience of location: we are a quick 25 minutes to Madison or a short drive from MKE + Chicago.

Guest favorite
An inviting outdoor space features a fire pit surrounded by several chairs, set on a brick patio. Soft lighting from string lights enhances the ambiance as the shimmering water of the Rock River is visible in the background.
Cottage in Edgerton
4.96 out of 5 average rating, 104 reviews

Quiet Waterfront 2BR w/Dock & Huge Patio

Escape to a charming cottage on the tranquil Rock River in Edgerton, WI, where each season offers unique beauty. In summer, enjoy kayaking, fishing, and boating. Fall brings vibrant foliage and crisp air, perfect for outdoor walks. Winter transforms the landscape into a serene, snow-covered wonderland. With picturesque views, modern amenities, and nature at your doorstep, this cozy retreat invites relaxation and adventure year-round. Watch the stars light up the night sky in any season.

Top guest favorite
Cottage in Mineral Point
4.82 out of 5 average rating, 267 reviews

Cottage on Clowney

Escape to a Charming 1849 Historic Cottage in the Heart of Mineral Point!! The cottage nestled just 2 blocks from Mineral Point's vibrant downtown. This cozy retreat offers the perfect blend of historic charm and modern comfort. Featuring 2 Bedrooms, Fully Stocked Kitchen, Off Street Parking, and Private backyard! Immerse yourself in the tranquility of this unique historic cottage. Unwind, relax, explore nearby art galleries and shops, and experience the charm of Mineral Point.

Top guest favorite
The exterior of a green cottage is surrounded by trees, featuring a welcoming front porch with a swing. A small bistro table and two red chairs are visible, complemented by natural landscaping of gravel and stones.
Cottage in Baraboo
4.96 out of 5 average rating, 182 reviews

Cottage near Devils Lake Baraboo

Welcome to our charming two-bedroom cottage, perfect for rejuvenation! It features a queen-sized and a full-sized bed, ideal for a small family or couple. Enjoy the double jetted tub or the luxury shower. A fully equipped kitchen, satellite TV, DVD player, and air-conditioning ensure comfort. Warm up by the Vermont wood-burning stove from November to April. Enjoy the pond view, Baraboo bluff, and meet our friendly horses and dogs. We look forward to welcoming you!

Guest favorite
The home is set on a spacious lot surrounded by mature trees, showcasing a welcoming exterior design with light-colored siding and a gabled roof. Lush greenery and flowering plants create a natural border along the pathway, leading to an inviting front porch.
Cottage in Lake Geneva
4.92 out of 5 average rating, 109 reviews

The Peacock Cottage

Cozy, quiet, accessible Lake Geneva home with large open living area, vaulted ceilings, large 1-acre wooded lot. 3 minutes from beach, 5 minutes to both Lake Geneva and Williams Bay, 2 minutes to a local Wisconsin-style convenience store. Welcome to the Peacock Cottage! Located on a deep, private lot surrounded by woods, so it's great to let loose without any nearby traffic. We are super into cozy homes, and love creating spaces that are restful and fun.

Top guest favorite
A serene view of the Wisconsin River is captured, reflecting soft hues of sunset in the calm water. Lush greenery lines the riverbank, creating a natural frame. Gentle ripples adorn the water's surface, enhancing the tranquility of the landscape.
Cottage in Muscoda
4.96 out of 5 average rating, 205 reviews

River's Edge Cabin, LLC

We welcome you to be our guest in our comfy, warm cabin nestled on the lower Wisconsin River. We are close to many area attractions including Frank Lloyd Wright's Taliesin, House on the Rock, American Players Theater, Wisconsin Dells, and much more! Activities include canoeing, fishing, hunting, shopping in quaint villages, or just relaxing watching the river... Our cabin is easy to get to and close to area villages but in a private setting.

Top guest favorite
A welcoming exterior of a cottage is surrounded by well-maintained green grass. Two bright pink Adirondack chairs are positioned in the front yard, inviting relaxation. The entrance features a porch with a circular decorative element, complemented by neatly arranged shrubs and trees.
Cottage in Lake Geneva
4.98 out of 5 average rating, 196 reviews

Seven Oaks Bed & Breakfast

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY.

Top guest favorite
Cottage in Lake Geneva
4.95 out of 5 average rating, 107 reviews

Cozy Lake Geneva Cottage | Near Lake & Town

Step back in time in this cozy retreat, filled with vintage charm that is tucked away near the peaceful Historic Maple District. Perfect for couples, small groups and families. ​The Location: ​0.9 Miles to Geneva Lake & Downtown: A flat, scenic stroll through the beautiful Historic Maple District - Many guests love the walk! ​8 min to Grand Geneva Resort & Spa​18 min to Burlington ​20 min to Alpine Valley

Top guest favorite
A serene lakeside view showcases the vibrant hues of a sunset over Lake Winnebago. Silhouetted trees line the shore, with the water reflecting the warm colors of the evening sky. The grassy foreground adds a natural element to the picturesque scene.
Cottage in Fond du Lac
4.93 out of 5 average rating, 146 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

Popular amenities for Madison cottage rentals

Quick stats about cottage rentals in Madison

  • Nightly prices starting at

    Madison vacation rentals start at G$18,815 GYD per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madison rentals

  • 4.9 Average rating

    Madison stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Madison's top spots, include Henry Vilas Zoo, Wisconsin State Capitol, and Olbrich Botanical Gardens

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