Cottage holiday rentals in Madison

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Top-rated cottage rentals in Madison

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Guest favourite

Cottage in Poynette

4.97 out of 5 average rating, 190 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

26 Sept – 3 Oct

£125 per night

Guest favourite

Cottage in Rockton

4.95 out of 5 average rating, 188 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

16–23 Sept

£143 per night

Guest favourite

Cottage in Arena

4.91 out of 5 average rating, 263 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.

17–24 Jan

£122 per night

Guest favourite

Cottage in Hartland

4.96 out of 5 average rating, 113 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.).

26 Jun – 3 Jul

£127 per night

Guest favourite

Cottage in Dane

4.88 out of 5 average rating, 685 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

Cottage in Baraboo

5.0 out of 5 average rating, 136 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*

5–12 Jan

£250 per night

Guest favourite

Cottage in Greenfield

4.97 out of 5 average rating, 130 reviews

Cottage near Devil's Lake, Baraboo, WI Dells

Pinehaven of Baraboo located near Devil's Lake and Wisconsin Dells is your destination for rest and relaxation. Our cottage boasts a charming country decor, two bedrooms, an indoor double jetted tub and separate shower. Fully stocked kitchen with full-size appliances, dining area, living room with flatscreen smart TV, satellite and DVD player. Forced air heat, central A/C and a Vermont wood stove (Nov 1 - Apr 1). Enjoy the birds, pond view, porch swing and bistro table on front porch.

25 Jun – 2 Jul

£202 per night

Guest favourite

Cottage in Edgerton

4.87 out of 5 average rating, 131 reviews

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.

6–13 May

£163 per night

Guest favourite

Cottage in Lena

4.95 out of 5 average rating, 157 reviews

Countryside Getaway at Kerlin Schoolhouse!

Welcome to Kerlin Schoolhouse! This Stone Cottage was built in 1870 and was originally a one-room schoolhouse! Kerlin Schoolhouse is located in a quiet, private, peaceful setting in the beautiful countryside. Featuring beautiful views with amazing sunrises, sunsets, windmills, and starry nights! Surrounded by corn fields on all 4 sides. The home features an open concept with loft bedroom & loft-style staircase. Featuring a fireplace, firepit & grill (seasonal), and more.

9–16 Jul

£111 per night

Guest favourite

Cottage in Pardeeville

4.91 out of 5 average rating, 129 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/tea, games, DVD player, DVD'S, 40” smartTV and Alexa. 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.

27 Dec – 3 Jan

£178 per night

Superhost

Cottage in Mineral Point

4.81 out of 5 average rating, 217 reviews

Cottage on Clowney

Built in 1849, Cottage on Clowney is 2 blocks away from the heart of Mineral Point making it easy to walk to the local shops, restaurants and historic destinations. The Cottage features a beautiful living room with amazing stone work making it extremely cozy, a separate reading nook and a welcoming kitchen, 2 bedrooms and a bathroom. Enjoy having a campfire in the back yard and the sheer quietness of the location. It is the perfect place to relax and recharge your batteries.

10–17 Feb

£132 per night

Guest favourite

Cottage in Fox Lake

4.85 out of 5 average rating, 285 reviews

The Little White Cabin, Fox Lake WI

****As of October 15, 2023, all of the piers are out of the water for the winter season.**** This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!

21–28 Feb

£117 per night