Cottage vacation rentals in Madison

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Madison

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

0 of 0 items showing

1 of 3 pages

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, 238 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 favorite

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

4.96 out of 5 average rating, 253 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

Guest favorite

The exterior of a charming cottage is depicted, featuring light gray siding and a welcoming front porch adorned with potted flowers. A well-manicured lawn and symmetrical hedges frame the path leading to the entrance. Trees provide a natural backdrop, with soft sunlight filtering through the leaves.

Cottage in Lake Geneva

4.95 out of 5 average rating, 131 reviews

NEW! Boutique Stay – Walk to Lake, Cafes & Shops!

Nestled in the heart of Lake Geneva's historic Maple Park, this chic and charming cottage offers the perfect setting for making memories. Relax on the porch, stroll to nearby coffee shops, restaurants, boutiques, the beach, or simply stay in to soak up the cottage charm. Thoughtfully restored and designed with timeless character, it’s the perfect setting for gathering with friends and family to make memories that last a lifetime. This retreat captures the spirit of classic Lake Geneva living.

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, 300 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.

Superhost

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.

Top guest favorite

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

4.99 out of 5 average rating, 180 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*

Superhost

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, 247 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.

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, 170 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!

Superhost

A cozy living area features a large picture window, offering views of the river and natural light. A light gray sofa and a comfortable armchair are positioned on a woven rug. Potted plants add a touch of greenery, while wooden accents complement the space.

Cottage in Edgerton

4.85 out of 5 average rating, 142 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 125' shoreline for 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.

Top guest favorite

The exterior of a charming cabin is framed by large, mature trees and well-maintained green lawns. A welcoming front entrance with a red door is visible, and surrounding landscaping includes shrubs and flower beds, creating a serene outdoor environment.

Cottage in Williams Bay

4.96 out of 5 average rating, 114 reviews

Peaceful, serene cottage near Lake Geneva

Welcome to Serenity. Not your typical lake cabin, Serenity has a Mid Century flair in a wooded, quiet and peaceful setting just minutes from the beach and boat launch on Williams Bay. Enjoy morning coffee in the large dining room as our neighborhood turkeys wander through the yard. There is an outdoor dining set with charcoal grill, and a gas fire pit to warm you up on cool nights, and an additional family room in the loft to play games or relax in front of the TV.

Superhost

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

4.91 out of 5 average rating, 103 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.

Guest favorite

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, 127 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.