Madison Vacation Rentals & Ski-in/Ski-out Homes
House
- Montevideo
- ·
- Ortonville
- 5.03 mi to center
9.2Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
8 Guests
2110 ft²
Balcony/Terrace
Kitchen
Air Conditioner
Internet
US $505/Night
7 Nights - US $3,535
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
14 Guests
3003.13 ft²
Oceanfront
Parking
Ocean View
View
US $205/Night
7 Nights - US $1,432
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
9.4Exceptional
(6 Reviews)
5 Bedrooms
2 Baths
20 Guests
4100 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $426/Night
7 Nights - US $2,982
Cabin
- Montevideo
- ·
- Ortonville
- 5.05 mi to center
10.0Exceptional
(135 Reviews)
4 Bedrooms
2 Baths
12 Guests
3200 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $344/Night
7 Nights - US $2,410
House
- Montevideo
- ·
- Ortonville
- 5.10 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
12 Guests
2400.35 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $156/Night
7 Nights - US $1,093
House
- Montevideo
- ·
- Ortonville
- 5.18 mi to center
10.0Exceptional
(80 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,727
Cabin
- South Dakota
- ·
- Big Stone City
- 4.00 mi to center
10.0Exceptional
(44 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,135
House
- Montevideo
- ·
- Ortonville
- 5.81 mi to center
10.0Exceptional
(32 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $458/Night
7 Nights - US $3,206
House
- Montevideo
- ·
- Ortonville
- 5.13 mi to center
10.0Exceptional
(29 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $240/Night
7 Nights - US $1,681
Luxury Places to Stay in Madison
Over 81+ Luxury Places to Stay in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 5.23 mi to center
4 Bedrooms
4 Baths
11 Guests
3187 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $696/Night
7 Nights - US $4,871
House
- Montevideo
- ·
- Ortonville
- 4.88 mi to center
9.6Exceptional
(8 Reviews)
4 Bedrooms
4 Baths
15 Guests
2796 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $670/Night
7 Nights - US $4,692
House
- Montevideo
- ·
- Ortonville
- 5.23 mi to center
4 Bedrooms
4 Baths
11 Guests
3186.12 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $596/Night
7 Nights - US $4,174
House
- Minnesota
- ·
- Chippewa County
- 15.16 mi to center
9.6Exceptional
(10 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $521/Night
7 Nights - US $3,649
House
- Montevideo
- ·
- Canby
- 9.01 mi to center
9.8Exceptional
(27 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $491/Night
7 Nights - US $3,435
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(68 Reviews)
3 Bedrooms
2 Baths
11 Guests
2800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $487/Night
7 Nights - US $3,407
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(41 Reviews)
4 Bedrooms
2 Baths
10 Guests
2100 ft²
- Parking
Spa- Balcony/Terrace
- Kitchen
US $453/Night
7 Nights - US $3,171
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
1 Bedroom
1 Bath
20 Guests
4101.05 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $447/Night
7 Nights - US $3,129
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
9.6Exceptional
(56 Reviews)
5 Bedrooms
2 Baths
20 Guests
4100 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $446/Night
7 Nights - US $3,124
Top-Rated Vacation Rentals with a Pool in Madison
Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Madison
Cabin
- Montevideo
- ·
- Ortonville
- 5.04 mi to center
9.6Exceptional
(15 Reviews)
4 Bedrooms
1 Bath
8 Guests
1850 ft²
- Parking
Pool- Balcony/Terrace
- Kitchen
US $387/Night
7 Nights - US $2,711
Hotel
- South Dakota
- ·
- Milbank
- 1.66 mi to center
9.4Exceptional
(317 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Kitchen
US $173/Night
7 Nights - US $1,210
Hotel
- Montevideo
- ·
- Canby
- 1.78 mi to center
9.4Exceptional
(257 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $123/Night
7 Nights - US $860
Hotel
- Montevideo
- ·
- Canby
- 1.76 mi to center
8.4Excellent
(43 Reviews)
8 Baths
301.39 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
US $115/Night
7 Nights - US $805
Hotel
- South Dakota
- ·
- Milbank
- 1.64 mi to center
8.1Excellent
(39 Reviews)
5 Baths
376.74 ft²
- Private Pool
- Hot Tub
EV Charge Station- Parking
US $179/Night
7 Nights - US $1,253
Hotel
- South Dakota
- ·
- Clear Lake
- 3.20 mi to center
6.4Good
(12 Reviews)
8 Baths
309.08 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $80/Night
7 Nights - US $560
House
- Montevideo
- ·
- Appleton
- 4.28 mi to center
10.0Exceptional
(24 Reviews)
5 Bedrooms
2 Baths
13 Guests
2704 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $420/Night
7 Nights - US $2,942
Cottage
- Montevideo
- ·
- Appleton
- 4.28 mi to center
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $270/Night
7 Nights - US $1,890
Pet-Friendly Vacation Rentals in Madison
Over 32+ Pet-Friendly Vacation Rentals in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
7 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $226/Night
7 Nights - US $1,584
Cabin
- Montevideo
- ·
- Ortonville
- 4.56 mi to center
8.8Fabulous
(75 Reviews)
32 Bedrooms
1 Bath
34 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $100/Night
7 Nights - US $698
House
- Montevideo
- ·
- Odessa
- 2.12 mi to center
10.0Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $204/Night
7 Nights - US $1,429
Apartment
- South Dakota
- ·
- Gary
- 5.12 mi to center
3 Bedrooms
1 Bath
6 Guests
2002.09 ft²
- Parking
- Pet Friendly
Child Friendly
Security/Safety
US $217/Night
7 Nights - US $1,519
House
- Montevideo
- ·
- Ortonville
- 5.07 mi to center
10.0Exceptional
(8 Reviews)
4 Bedrooms
1 Bath
7 Guests
2300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $348/Night
7 Nights - US $2,438
Apartment
- South Dakota
- ·
- Gary
- 5.12 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $214/Night
7 Nights - US $1,498
Cabin
- South Dakota
- ·
- Brandt
- 8.31 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $342/Night
7 Nights - US $2,396
House
- Montevideo
- ·
- Ortonville
- 8.81 mi to center
9.6Exceptional
(95 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $192/Night
7 Nights - US $1,347
Apartment
- Minnesota
- ·
- Montevideo
- 3.97 mi to center
9.6Exceptional
(37 Reviews)
1 Bedroom
1 Bath
5 Guests
500 ft²
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
US $131/Night
7 Nights - US $916
Large Vacation Homes & Villas in Madison
Over 14+ Large Vacation Homes & Villas in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 5.10 mi to center
9.2Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
12 Guests
2400 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $177/Night
7 Nights - US $1,236
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
9.2Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
14 Guests
3000 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $195/Night
7 Nights - US $1,366
Cabin
- South Dakota
- ·
- Big Stone City
- 2.80 mi to center
7.0Very Good
(2 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Pet Friendly
US $276/Night
7 Nights - US $1,935
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
3 Bedrooms
2 Baths
12 Guests
4000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,698
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
9.4Exceptional
(22 Reviews)
7 Bedrooms
3 Baths
20 Guests
4100 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $457/Night
7 Nights - US $3,199
Cabin
- Montevideo
- ·
- Ortonville
- 8.45 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,855
Cabin
- Montevideo
- ·
- Ortonville
- 5.28 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $361/Night
7 Nights - US $2,527
House
- Montevideo
- ·
- Madison
- 6.54 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
2600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $395/Night
7 Nights - US $2,767
Cottage
- Montevideo
- ·
- Ortonville
- 8.05 mi to center
9.8Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
10 Guests
2000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $329/Night
7 Nights - US $2,303
Wheelchair Accessible Vacation Homes in Madison
Over 3+ Wheelchair Accessible Vacation Homes in or Near Madison
Hotel
- South Dakota
- ·
- Gary
- 4.96 mi to center
7.4Very Good
(18 Reviews)
4 Baths
Private Beach- Oceanfront
- Breakfast
- Parking
US $134/Night
7 Nights - US $936
Hotel
- South Dakota
- ·
- Milbank
- 1.72 mi to center
6.6Good
(72 Reviews)
11 Baths
292.58 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $65/Night
7 Nights - US $454
Hotel
- Minnesota
- ·
- Montevideo
- 5.15 mi to center
5.6Average
(30 Reviews)
4 Baths
414.41 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $72/Night
7 Nights - US $504
Madison Resorts and Airbnb Homes Under $200
Over 19+ Madison Resorts and Airbnb Homes Under $200
Cabin
- South Dakota
- ·
- Big Stone City
- 3.12 mi to center
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
Bedding/Linens
Wellness Facilities
US $165/Night
7 Nights - US $1,154
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
2 Bedrooms
1 Bath
6 Guests
947.22 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $189/Night
7 Nights - US $1,321
Hotel
- Montevideo
- ·
- Ortonville
- 4.55 mi to center
8.8Fabulous
(390 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $110/Night
7 Nights - US $767
House
- Montevideo
- ·
- Ortonville
- 4.79 mi to center
8.6Fabulous
(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $193/Night
7 Nights - US $1,354
Hotel
- Minnesota
- ·
- Montevideo
- 4.94 mi to center
9.0Exceptional
(66 Reviews)
1 Bath
1550 ft²
- Parking
- Air Conditioner
- Pet Friendly
- Child Friendly
US $86/Night
7 Nights - US $599
House
- South Dakota
- ·
- Big Stone City
- 5.68 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $109/Night
7 Nights - US $762
Apartment
- Montevideo
- ·
- Madison
- 1.47 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $165/Night
7 Nights - US $1,152
House
- Montevideo
- ·
- Ortonville
- 4.99 mi to center
9.8Exceptional
(47 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $95/Night
7 Nights - US $665
House
- Montevideo
- ·
- Ortonville
- 5.09 mi to center
8.4Excellent
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $836
Instantly Bookable Vacation Homes in Madison
Over 22+ Instantly Bookable Vacation Homes in or Near Madison
Cabin
- South Dakota
- ·
- Big Stone City
- 5.83 mi to center
10.0Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $444/Night
7 Nights - US $3,105
House
- Minnesota
- ·
- Montevideo
- 4.35 mi to center
10.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $203/Night
7 Nights - US $1,420
Cabin
- Montevideo
- ·
- Ortonville
- 4.94 mi to center
9.8Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $281/Night
7 Nights - US $1,965
Cabin
- Montevideo
- ·
- Ortonville
- 9.64 mi to center
9.6Exceptional
(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,454
House
- Montevideo
- ·
- Ortonville
- 4.76 mi to center
9.2Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,623
House
- Montevideo
- ·
- Ortonville
- 5.24 mi to center
9.0Exceptional
(43 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $244/Night
7 Nights - US $1,708
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
7.0Very Good
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $255/Night
7 Nights - US $1,782
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
1 Bedroom
1 Bath
6 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $218/Night
7 Nights - US $1,529
House
- Montevideo
- ·
- Ortonville
- 5.24 mi to center
10.0Exceptional
(31 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $264/Night
7 Nights - US $1,846
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 90 vacation rentals in Madison with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Madison for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Madison. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Madison tailored to your preferences. On average, these rentals offer 1023.7 ft² of space, and are priced at an average of US $271 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Madison at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Madison
| Type | Count |
|---|---|
| Vacation Homes | 47 |
| Cabin Rentals | 15 |
| Holiday Apartments | 8 |
| Cottages | 3 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Madison
★ Pro Tip: Discover Your Ideal Vacation Rental in Madison with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Madison, MN
View the weather forecast for Madison before booking your Madison Vacation Rentals to confirm your best time to go.
December - February
High 30°F Low -1°F
March - May
High 66°F Low 18°F
June - August
High 82°F Low 52°F
September - November
High 71°F Low 18°F
Top Attractions Around Madison, MN
Sunski offers a large selection of top attractions around Madison . Research things to do on your vacation before you visit Madison.
Other Places to Stay in Madison, MN
Frequently Asked Questions About Madison?
What are the top vacation rentals in Madison?
When organizing your trip to Madison, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Madison. Peruse our collection of highly-rated properties and secure your reservation today.
- Waterfront Big Stone Lake Home w/Dock & Views
- Big Stone Lake Family Cabin: LAKEFRONT with boat dock!
- Cozy 2-bedroom cabin with WiFi, AC in serene Big Stone City
- Spacious home with a large deck and ample space for beautiful sunset viewing!
- The Mulberry House near the south shore of Big Stone Lake
- Cozy Home by boat launch, park, dock and downtown Ortonville and Big Stone
- Odessa Lodge 3bd/2ba-Close to hunting, fishing, hiking and Lake Fun
- 1BR cabin on Big Stone Lake
- Big Stone Lake, SD-Bayview area Lake Cabin
- 4 SEASON LAKE HOUSE RETREAT Private Dock,Sunsets,Family Friendly,Hunters Welcome
Which vacation homes or resorts in Madison are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Madison. Enjoy great views, locations and save money with SunSki Resorts.™
- Enjoy this peaceful house on Big Stone Lake!
- Walkable Main St Studio Near Lake Cochrane
- Lantern Motel
How many SunSkiResorts vacation rentals or resorts are available in Madison?
Discover the ideal vacation rental in Madison with SunSki Resorts™. We provide an extensive selection of over 90 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Madison.
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