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Cottage holiday 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 favourite
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, 248 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, 306 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.

Guest favourite
Cottage in Princeton
4.96 out of 5 average rating, 225 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 favourite
A recently renovated kitchen features stainless steel appliances and white cabinetry. Two windows allow natural light to fill the space, and a decorative plant enhances the aesthetic. A countertop with a marble-like finish provides ample workspace beside the stove and microwave.
Cottage in Baraboo
4.98 out of 5 average rating, 198 reviews

Cozy Farmhouse close to Devils Lake & Wis. Dells

Newly renovated and Listed July 2021!! *discount passes to some dells attractions* Relax with the whole family at this peaceful place to stay. This newly renovated farmhouse is conveniently located between Baraboo and Wisconsin Dells. This property has 3 bedrooms and 2 baths, sleeps up to 10 people, Sleeps 8 in beds additional futon and large sectional in basement. It is equipped with a game room in the basement with a pool table and air hockey table, along with other games. *inquire*

Guest favourite
Cottage in Edgerton
4.86 out of 5 average rating, 157 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 favourite
Cottage in Edgerton
4.96 out of 5 average rating, 101 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 favourite
Cottage in Mineral Point
4.82 out of 5 average rating, 266 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 favourite
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 favourite
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 favourite
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, 130 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 favourite
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, 192 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 favourite
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

Popular amenities for cottage rentals in Madison

Quick stats about cottage rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at € 77 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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