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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Guest favourite

Cottage in Williams Bay

4.98 out of 5 average rating, 125 reviews

Clover Cottage in Williams Bay - with Hot Tub!

Welcome to Clover Cottage, a non-smoking, family friendly home with modern updates, within short walk of beach, lake, coffee and restaurants (and ice-cream shops!). Enjoy coffee or tea on the porch and relax in the spacious backyard with Hot tub, grill and fire pit. Beach is 0.7mi walk. Kitchen is fully equipped, including blender, Keurig, espresso maker, and more. Local attractions include Music by the Lake, Kishwauketoe Nature Conservancy, Yerkes Observatory, and more Baby gate provided.

Top guest favourite

Cottage in Poynette

4.96 out of 5 average rating, 223 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

Cottage in Rockton

4.96 out of 5 average rating, 231 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

Cottage in Arena

4.89 out of 5 average rating, 290 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 Hartland

4.95 out of 5 average rating, 136 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.).

Top guest favourite

Cottage in Baraboo

4.99 out of 5 average rating, 169 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 Lake Geneva

4.94 out of 5 average rating, 117 reviews

Chic & Charming - walkable to everything!

Nestled in the heart of Lake Geneva's historic Maple Park neighborhood, this chic and charming 125-year-old cottage seamlessly blends timeless character with modern sophistication. Meticulously restored and thoughtfully designed, it offers an inviting blend of historic charm and contemporary luxury. Perfect for a tranquil retreat or lively gatherings, this enchanting haven provides the ultimate escape from city life, creating the perfect setting for unforgettable Lake Geneva memories.

Guest favourite

Cottage in Wonder Lake

4.93 out of 5 average rating, 137 reviews

The Cozy Lake House/ Perfect Winter Getaway!DM ?s

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!

Guest favourite

Cottage in Pardeeville

4.9 out of 5 average rating, 155 reviews

Lake View Retreat

A perfect spot to escape! Just a short stroll to Park Lake with stunning sunsets. Our cozy cottage/lake view is just what you need to relax and unwind after the day's adventures. A stocked kitchen/LR with coffee, games, DVD player, DVD'S, 40” smartTV. Prime location to all things fun! Lake activities, hiking, exploring in the summer and ice fishing, downhill skiing and snowmobiling in the winter! We love sharing our space and know you will love it just as much.

Guest favourite

Cottage in Hustisford

4.96 out of 5 average rating, 114 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

Cottage in Baraboo

4.97 out of 5 average rating, 152 reviews

Cottage · Cottage · Relaxing Cottage near Devils L

Escape to Pinehaven Cottage, a cozy getaway near Devil's Lake and Wisconsin Dells. This charming cottage features two bedrooms, an indoor double-jetted tub, and a fully stocked kitchen. Unwind in the living room with satellite TV, enjoy the warmth of a Vermont wood stove, or savor nature from the porch swing. The beautiful Baraboo bluffs and a serene 2-acre pond complete this tranquil setting. Book now to create lasting memories at Pinehaven!

Guest favourite

Cottage in Fontana-on-Geneva Lake

4.98 out of 5 average rating, 103 reviews

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

4 Bedroom 2 1/2 bath vacation cottage in Abbey Springs Resort Community on Lake Geneva. Resort Pass is required for all guests (included) and gives entry to the resort plus indoor and outdoor pool (Memorial to Labor Day), hot tub, games room , gym, tennis courts , pickle ball. 2 restaurants beach and fire pit on site. Newly Renovated Golf Course not included but available by paying at club house . We welcome all .