Cottage holiday rentals in Madison

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

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.

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.

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.

Rock River Rest | peaceful waterfront cottage

Escape the city to your private waterfront retreat. Nestled among centuries old Oaks, our expansive backyard with 125' shoreline allows for direct river access to water activities + Lake Koshkonong. Or sit back and relax while watching wildlife out the large picture windows and listening to vintage vinyl. Carefully curated amenities make the cottage perfect for a romantic getaway, remote work or artist retreat. Ideally located 30 min from Madison or a short drive from MKE + Chicago.

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.

The Cozy Lake House/Perfect Lake Front Getaway!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

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.

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.