Madison Vacation Rentals & Ski-in/Ski-out Homes
New
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
1 Bedroom
1 Bath
6 Guests
2000 ft²
Parking
Kitchen
Air Conditioner
Internet
US $288/Night
7 Nights - US $2,016
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 $208/Night
7 Nights - US $1,456
Hotel
- South Dakota
- ·
- Milbank
- 1.66 mi to center
9.4Exceptional
(293 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
US $184/Night
7 Nights - US $1,286
Cabin
- Montevideo
- ·
- Ortonville
- 5.05 mi to center
10.0Exceptional
(128 Reviews)
4 Bedrooms
2 Baths
12 Guests
3200 ft²
Hot Tub- Parking
- Ocean View
Balcony/Terrace
US $424/Night
7 Nights - US $2,971
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 $222/Night
7 Nights - US $1,553
House
- Montevideo
- ·
- Ortonville
- 5.18 mi to center
10.0Exceptional
(73 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,731
House
- Montevideo
- ·
- Ortonville
- 5.13 mi to center
10.0Exceptional
(27 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $223/Night
7 Nights - US $1,558
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 $226/Night
7 Nights - US $1,579
Cabin
- South Dakota
- ·
- Big Stone City
- 3.12 mi to center
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
Child Friendly
Bedding/Linens
US $165/Night
7 Nights - US $1,154
Luxury Places to Stay in Madison
Over 77+ Luxury Places to Stay in or Near Madison
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 $1,120/Night
7 Nights - US $7,837
House
- Montevideo
- ·
- Ortonville
- 4.88 mi to center
9.6Exceptional
(8 Reviews)
4 Bedrooms
4 Baths
15 Guests
2796 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $641/Night
7 Nights - US $4,487
House
- Minnesota
- ·
- Chippewa County
- 15.16 mi to center
10.0Exceptional
(5 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
(36 Reviews)
4 Bedrooms
2 Baths
10 Guests
2100 ft²
- Parking
Spa- Ocean View
- Balcony/Terrace
US $479/Night
7 Nights - US $3,353
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(63 Reviews)
3 Bedrooms
2 Baths
11 Guests
2800 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $443/Night
7 Nights - US $3,100
Cabin
- South Dakota
- ·
- Big Stone City
- 5.83 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $401/Night
7 Nights - US $2,804
Cabin
- Montevideo
- ·
- Ortonville
- 5.04 mi to center
9.8Exceptional
(13 Reviews)
4 Bedrooms
1 Bath
8 Guests
1850 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $391/Night
7 Nights - US $2,738
Cabin
- South Dakota
- ·
- Brandt
- 8.31 mi to center
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $369/Night
7 Nights - US $2,583
Top-Rated Vacation Rentals with a Pool in Madison
Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 8.81 mi to center
9.6Exceptional
(93 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $189/Night
7 Nights - US $1,324
Hotel
- Montevideo
- ·
- Canby
- 1.78 mi to center
9.4Exceptional
(239 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 $169/Night
7 Nights - US $1,183
Hotel
- South Dakota
- ·
- Clear Lake
- 3.20 mi to center
7.1Very Good
(12 Reviews)
7 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 29+ Pet-Friendly Vacation Rentals in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
7 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $225/Night
7 Nights - US $1,577
Cabin
- Montevideo
- ·
- Ortonville
- 4.56 mi to center
8.8Fabulous
(60 Reviews)
32 Bedrooms
1 Bath
34 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $108/Night
7 Nights - US $758
Cabin
- Minnesota
- ·
- Chippewa County
- 14.00 mi to center
9.6Exceptional
(145 Reviews)
1 Bedroom
1 Bath
5 Guests
550 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $148/Night
7 Nights - US $1,037
New
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 $268/Night
7 Nights - US $1,873
House
- Montevideo
- ·
- Ortonville
- 5.10 mi to center
9.6Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
12 Guests
2400 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $189/Night
7 Nights - US $1,321
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
9.2Exceptional
(15 Reviews)
4 Bedrooms
2 Baths
14 Guests
3000 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $202/Night
7 Nights - US $1,415
House
- Montevideo
- ·
- Ortonville
- 5.24 mi to center
9.0Exceptional
(43 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $245/Night
7 Nights - US $1,715
House
- Montevideo
- ·
- Ortonville
- 4.76 mi to center
9.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,623
House
- Montevideo
- ·
- Ortonville
- 4.79 mi to center
8.6Fabulous
(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $191/Night
7 Nights - US $1,338
Large Vacation Homes & Villas in Madison
Over 12+ Large Vacation Homes & Villas in or Near Madison
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
House
- Montevideo
- ·
- Ortonville
- 5.81 mi to center
10.0Exceptional
(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $383/Night
7 Nights - US $2,679
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
Lake View- Balcony/Terrace
US $329/Night
7 Nights - US $2,303
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 $472/Night
7 Nights - US $3,306
House
- Montevideo
- ·
- Ortonville
- 5.05 mi to center
5.0Average
(62 Reviews)
3 Bedrooms
3 Baths
12 Guests
3400 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $330/Night
7 Nights - US $2,310
Cabin
- South Dakota
- ·
- Brandt
- 8.32 mi to center
4 Bedrooms
3 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $529/Night
7 Nights - US $3,700
Wheelchair Accessible Vacation Homes in Madison
Over 4+ Wheelchair Accessible Vacation Homes in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 4.99 mi to center
9.8Exceptional
(47 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $95/Night
7 Nights - US $665
Hotel
- South Dakota
- ·
- Gary
- 4.96 mi to center
7.4Very Good
(18 Reviews)
4 Baths
Private Beach- Oceanfront
- Breakfast
- Parking
US $113/Night
7 Nights - US $794
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 $66/Night
7 Nights - US $460
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 17+ Madison Resorts and Airbnb Homes Under $200
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
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
2 Bedrooms
1 Bath
7 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
(375 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $110/Night
7 Nights - US $767
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
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
Apartment
- Minnesota
- ·
- Montevideo
- 3.97 mi to center
9.6Exceptional
(33 Reviews)
1 Bedroom
1 Bath
5 Guests
500 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $118/Night
7 Nights - US $829
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
House
- South Dakota
- ·
- Big Stone City
- 5.47 mi to center
7.4Very Good
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Child Friendly
US $126/Night
7 Nights - US $882
House
- South Dakota
- ·
- Brandt
- 8.35 mi to center
5.0Average
(6 Reviews)
1 Bedroom
2 Baths
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $137/Night
7 Nights - US $959
Instantly Bookable Vacation Homes in Madison
Over 17+ Instantly Bookable Vacation Homes in or Near Madison
House
- Minnesota
- ·
- Montevideo
- 4.35 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $271/Night
7 Nights - US $1,894
Cabin
- Montevideo
- ·
- Ortonville
- 4.94 mi to center
9.8Exceptional
(26 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $281/Night
7 Nights - US $1,965
Cabin
- Montevideo
- ·
- Ortonville
- 9.64 mi to center
9.6Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,469
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
7.0Very Good
(2 Reviews)
2 Bedrooms
1 Bath
7 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $250/Night
7 Nights - US $1,747
New
Apartment
- South Dakota
- ·
- Gary
- 5.12 mi to center
3 Bedrooms
1 Bath
6 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $207/Night
7 Nights - US $1,446
New
House
- Montevideo
- ·
- Ortonville
- 5.07 mi to center
4 Bedrooms
1 Bath
7 Guests
2300 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $246/Night
7 Nights - US $1,723
Cabin
- South Dakota
- ·
- Big Stone City
- 4.00 mi to center
10.0Exceptional
(33 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $213/Night
7 Nights - US $1,492
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
House
- South Dakota
- ·
- Big Stone City
- 4.61 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
8 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $239/Night
7 Nights - US $1,670
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 86 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 909.42 ft² of space, and are priced at an average of US $267 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 | 44 |
| Cabin Rentals | 15 |
| Holiday Apartments | 7 |
| 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
- The Mulberry House near the south shore of Big Stone Lake
- Odessa Lodge 3bd/2ba-Close to hunting, fishing, hiking and Lake Fun
- 1BR cabin on Big Stone Lake
- Cozy Home by boat launch, park, dock and downtown Ortonville and Big Stone
- Big Stone Lake, SD-Bayview area Lake Cabin
- Peaceful Lake Home Retreat
- The 7th Street Charmer - Fully Remodeled
- Family Shoreline Hideaway
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.™
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 86 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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