Cottage vacation rentals in Madison

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Top-rated cottage rentals in Madison

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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, 242 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

Top guest favourite
The exterior of the countryside cottage is displayed, featuring a charming facade with light gray siding and a welcoming sign. Lush green grass surrounds the home, complemented by landscaped garden beds filled with blooming bushes. A cozy porch is visible, with seating arrangements enhancing outdoor leisure.
Cottage in Rockton
4.97 out of 5 average rating, 258 reviews

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

Superhost
A serene view over a body of water reflects the vibrant colors of sunset, including orange and pink hues, while clouds create patterns across the sky. The surrounding hills frame the scene, creating a peaceful and natural atmosphere.
Cottage in Poynette
4.82 out of 5 average rating, 100 reviews

The Bobber Simple Cabin -Quaint 1BR/1BA-perfect HQ

This cottage is located in a beautiful rural setting. Set back off the main street with a private dead-end gravel drive. It's quiet and dark - perfect for stargazing. This is a simple, clean, and affordable space for those who are looking to get closer to nature. Conveniently located nearly equidistant to Madison, Wisconsin Dells, and Devil's Lake State Park. A wonderful HQ for exploring the natural beauty of Driftless Wisconsin. Plenty of hiking, skiing, breweries, wineries, and agri-tourism.

Superhost
Two vibrant yellow kayaks are positioned on a wooden dock, with their bright interiors visible. The serene Fox River can be seen in the background, framed by bare trees reflecting the tranquility of the surrounding nature.
Cottage in Princeton
4.96 out of 5 average rating, 215 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
A winding gravel path meanders through lush fields of green and tall corn plants, framed by overhanging trees. Soft sunlight filters through the branches, illuminating the pathway that leads deeper into the countryside.
Cottage in Dane
4.87 out of 5 average rating, 737 reviews

The Napping Farm

For ten years we have welcomed travelers from all over the world to our cozy and unique farm house and we would love to host you, come as you are. If you can, please read all information provided in this listing. This is a private country house on 120 acres of woods and fields, cut in with trails, in Wisconsin's Driftless Region. Located 30 min to Devil's lake, 45 to Wisconsin Dells and only 25 Minutes to downtown Madison. Events or a party, Common Gardens for more details, we love events.

Guest favourite
The exterior of the historic cottage features a blend of stone and wooden siding, showcasing two stories with multiple windows. Lush greenery surrounds the structure, adding a natural element. A unique stone chimney stands prominently, highlighting the cottage's rustic charm.
Cottage in Mineral Point
4.81 out of 5 average rating, 253 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, 174 reviews

Relaxing Cottage near Devils Lake Baraboo WI Dells

Welcome to our charming two-bedroom cottage, perfect for relaxation and 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
Two wooden Adirondack chairs are positioned on a grassy area along the water's edge, facing a calm river. Reflections of trees and the surrounding landscape are visible in the still water, creating a serene outdoor setting.
Cottage in Edgerton
4.85 out of 5 average rating, 148 reviews

Rock River Rest quiet river stay 25 min to Madison

Escape the city to your own waterfront retreat. Nestled among centuries old Oaks along the Rock River, enjoy our cozy 1920s cottage and private backyard with direct river access. Relax while watching wildlife out the picture window and listening to vintage vinyl or jump in the car for an easy commute to UW-Madison/Epic. The cottage is ideal for a romantic getaway, remote work or artist retreat. Located 30 min from Madison or a short drive from MKE + Chicago.

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 relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.
Cottage in Fond du Lac
4.99 out of 5 average rating, 295 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 favourite
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, 203 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 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, 168 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.

Popular amenities for Madison cottage rentals

Quick stats about cottage rentals in Madison

  • Nightly prices starting at

    Madison vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 190 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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