
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Madison
Cottage rentals with a hot tub

Cottage in Wisconsin Dells
4.68 out of 5 average rating, 40 reviewsChristmas Mountain Village - 2BR Cottage 2

Cottage in Wisconsin Dells
4.67 out of 5 average rating, 9 reviewsChristmas Mountain Village - 2BR Cottage 8

Cottage in Wisconsin Dells
4.84 out of 5 average rating, 50 reviewsEnjoy Fun & Relaxation This Winter in Wis. Dells!

Cottage in Wisconsin Dells
4.78 out of 5 average rating, 9 reviewsChristmas Mountain Village two bedroom cottage
Pet-friendly cottage rentals

Cottage in Lake Mills
4.9 out of 5 average rating, 41 reviewsQuiet Cottage-Lakeview-Full Gym-$0 Cleaning Fee

Cottage in Edgerton
5 out of 5 average rating, 43 reviewsRock River Hideaway - Waterfront w/ Dock

Cottage in Hustisford
5 out of 5 average rating, 60 reviewsCharming Lakeside Cottage

Cottage in Williams Bay
4.93 out of 5 average rating, 44 reviewsA vintage charming 2-bedroom cottage!

Cottage in McFarland
4.96 out of 5 average rating, 70 reviewsCute & Cozy Cottage

Cottage in Wisconsin Dells
5 out of 5 average rating, 10 reviewsRustic King Cottage @ Sandstone Rustic Retreat

Cottage in Mineral Point
5 out of 5 average rating, 3 reviewsCozy Cottage w/ Driftless Views

Cottage in Poynette
4.91 out of 5 average rating, 53 reviewsNorth Cliff Cabin on Lake Wisconsin
Private cottage rentals

Cottage in Elkhorn
4.75 out of 5 average rating, 95 reviewsStonefire Cottage at Lake Wandawega

Cottage in Lake Geneva
5 out of 5 average rating, 27 reviewsCozy Como Getaway

Cottage in Lake Geneva
4.97 out of 5 average rating, 91 reviewsClose to Town + Beach • Historic Pemberley Cottage

Cottage in Fort Atkinson
4.94 out of 5 average rating, 36 reviewsHummingbird Haven Cottage on Lake Koshkonong

Cottage in Lake Geneva
5 out of 5 average rating, 24 reviewsQuaint and cozy cottage

Cottage in Wisconsin Dells
4.85 out of 5 average rating, 52 reviewsHilltop haven. relax…relax…relax

Cottage in McFarland
5 out of 5 average rating, 10 reviewsCozy Cottage on Lake Kegonsa

Cottage in Lodi
4.94 out of 5 average rating, 47 reviewsSunset Cottage at Lake Wi. Newly Remodeled!!!
Destinations to explore
- Milwaukee Holiday rentals
- Wisconsin Dells Holiday rentals
- Lake Geneva Holiday rentals
- Galena Holiday rentals
- Oshkosh Holiday rentals
- Rockford Holiday rentals
- Appleton Holiday rentals
- Schaumburg Holiday rentals
- Dubuque Holiday rentals
- Sheboygan Holiday rentals
- Lake Delton Holiday rentals
- Chicago Holiday rentals
- Cottage rentals Wisconsin
- Flat rentals Madison
- Rentals with outdoor seating Madison
- Rentals with breakfast Madison
- Waterfront rentals Madison
- Rentals with a hot tub Madison
- Villa rentals Madison
- Rentals with beach access Madison
- Monthly Rentals Madison
- Private suite rentals Madison
- Rentals with an EV charger Madison
- Pet-friendly rentals Madison
- Cabin rentals Madison
- Rentals with pools Madison
- Serviced apartment rentals Madison
- Rentals with lake access Madison
- Hotel rentals Madison
- Rentals with a fireplace Madison
- Rentals with a washing machine and dryer Madison
- Rentals with a firepit Madison
- Family-friendly rentals Madison
- Fitness-friendly rentals Madison
- Rentals with a patio Madison
- Apartment rentals Madison
- Family-friendly rentals Madison
- House rentals Madison
- Cottage rentals Wisconsin Dells
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom