87+ Vacation Home Rentals in Madison |
Madison Vacation Rentals & Ski-in/Ski-out Homes
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
1 Bedroom
1 Bath
6 Guests
2000 ft²
Fireplace/Heating
Pet Friendly
Kitchen
Parking
US $214/Night
7 Nights - US $1,501
House
- Montevideo
- ·
- Ortonville
- 5.09 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
6 Guests
1097.92 ft²
- Fireplace/Heating
View- Pet Friendly
Air Conditioner
US $238/Night
7 Nights - US $1,666
Hotel
- South Dakota
- ·
- Milbank
- 1.66 mi to center
9.4Exceptional
(283 Reviews)
1 Bath
- Fireplace/Heating
Pool
Breakfast- Kitchen
US $162/Night
7 Nights - US $1,134
Cabin
- Montevideo
- ·
- Ortonville
- 5.05 mi to center
10.0Exceptional
(123 Reviews)
4 Bedrooms
2 Baths
12 Guests
3200 ft²
Hot Tub- Fireplace/Heating
Ocean View
Balcony/Terrace
US $592/Night
7 Nights - US $4,145
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
14 Guests
3003.13 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
US $208/Night
7 Nights - US $1,456
House
- Montevideo
- ·
- Ortonville
- 5.18 mi to center
10.0Exceptional
(69 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $169/Night
7 Nights - US $1,182
Cabin
- South Dakota
- ·
- Big Stone City
- 4.00 mi to center
10.0Exceptional
(33 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $213/Night
7 Nights - US $1,492
House
- Montevideo
- ·
- Ortonville
- 7.66 mi to center
10.0Exceptional
(30 Reviews)
4 Bedrooms
2 Baths
10 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $50/Night
7 Nights - US $350
House
- Montevideo
- ·
- Ortonville
- 5.81 mi to center
10.0Exceptional
(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $387/Night
7 Nights - US $2,712
Luxury Places to Stay in Madison
Over 78+ 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
- Fireplace/Heating
- Ocean View
- View
US $1,120/Night
7 Nights - US $7,837
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
9.6Exceptional
(54 Reviews)
5 Bedrooms
2 Baths
20 Guests
4100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $797/Night
7 Nights - US $5,577
House
- Montevideo
- ·
- Ortonville
- 4.88 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
4 Baths
15 Guests
2796 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $533/Night
7 Nights - US $3,733
House
- Minnesota
- ·
- Chippewa County
- 15.16 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $425/Night
7 Nights - US $2,978
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(34 Reviews)
4 Bedrooms
2 Baths
10 Guests
2100 ft²
Spa- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $418/Night
7 Nights - US $2,923
House
- Montevideo
- ·
- Canby
- 9.01 mi to center
9.8Exceptional
(23 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $415/Night
7 Nights - US $2,903
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
11 Guests
2800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $398/Night
7 Nights - US $2,788
Other
- Minnesota
- ·
- Yellow Medicine County
- 1.62 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $374/Night
7 Nights - US $2,618
House
- Montevideo
- ·
- Ortonville
- 5.03 mi to center
8.8Fabulous
(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
2110 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $371/Night
7 Nights - US $2,594
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
9.8Exceptional
(13 Reviews)
4 Bedrooms
1 Bath
8 Guests
1850 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $266/Night
7 Nights - US $1,860
Other
- Montevideo
- ·
- Ortonville
- 8.81 mi to center
9.6Exceptional
(91 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $187/Night
7 Nights - US $1,309
Hotel
- Montevideo
- ·
- Canby
- 1.78 mi to center
9.4Exceptional
(232 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
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
- Fireplace/Heating
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
- Pool
- Pet Friendly
US $169/Night
7 Nights - US $1,183
Hotel
- South Dakota
- ·
- Clear Lake
- 3.20 mi to center
6.5Good
(8 Reviews)
7 Baths
309.08 ft²
- Private Pool
- Fireplace/Heating
- 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
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $420/Night
7 Nights - US $2,942
Cottage
- Montevideo
- ·
- Appleton
- 4.28 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $270/Night
7 Nights - US $1,890
Pet-Friendly Vacation Rentals in Madison
Over 28+ Pet-Friendly Vacation Rentals in or Near Madison
House
- Montevideo
- ·
- Odessa
- 2.12 mi to center
10.0Exceptional
(16 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $183/Night
7 Nights - US $1,282
Cabin
- Montevideo
- ·
- Ortonville
- 4.56 mi to center
8.8Fabulous
(54 Reviews)
32 Bedrooms
1 Bath
34 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $105/Night
7 Nights - US $735
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
7 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $190/Night
7 Nights - US $1,327
New
Apartment
- South Dakota
- ·
- Gary
- 5.12 mi to center
3 Bedrooms
1 Bath
6 Guests
2002.09 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Child Friendly
US $268/Night
7 Nights - US $1,873
Cabin
- Minnesota
- ·
- Chippewa County
- 14.00 mi to center
9.6Exceptional
(145 Reviews)
1 Bedroom
1 Bath
5 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $111/Night
7 Nights - US $774
Apartment
- Minnesota
- ·
- Montevideo
- 3.97 mi to center
9.6Exceptional
(25 Reviews)
1 Bedroom
1 Bath
5 Guests
500 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $92/Night
7 Nights - US $646
House
- Montevideo
- ·
- Ortonville
- 5.10 mi to center
9.6Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
12 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $220/Night
7 Nights - US $1,543
House
- Montevideo
- ·
- Ortonville
- 5.12 mi to center
9.2Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
14 Guests
3000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $271/Night
7 Nights - US $1,900
House
- Montevideo
- ·
- Ortonville
- 4.76 mi to center
9.2Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,064
Large Vacation Homes & Villas in Madison
Over 11+ Large Vacation Homes & Villas in or Near Madison
House
- Montevideo
- ·
- Ortonville
- 5.13 mi to center
10.0Exceptional
(23 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $185/Night
7 Nights - US $1,292
House
- Montevideo
- ·
- Ortonville
- 5.10 mi to center
1 Bedroom
1 Bath
12 Guests
2400.35 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $189/Night
7 Nights - US $1,325
House
- South Dakota
- ·
- Big Stone City
- 5.75 mi to center
9.4Exceptional
(22 Reviews)
7 Bedrooms
3 Baths
20 Guests
4100 ft²
- Fireplace/Heating
- 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
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
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
- Fireplace/Heating
- 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
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
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
- Fireplace/Heating
- Ocean View
Lake View- Balcony/Terrace
US $329/Night
7 Nights - US $2,303
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
- Fireplace/Heating
- 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
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
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
- Spa
- Fireplace/Heating
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
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $66/Night
7 Nights - US $460
Hotel
- Minnesota
- ·
- Montevideo
- 5.15 mi to center
5.6Average
(30 Reviews)
4 Baths
414.41 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $72/Night
7 Nights - US $504
Madison Resorts and Airbnb Homes Under $200
Over 21+ Madison Resorts and Airbnb Homes Under $200
Cabin
- South Dakota
- ·
- Big Stone City
- 3.12 mi to center
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Child Friendly
US $150/Night
7 Nights - US $1,050
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
2 Bedrooms
1 Bath
7 Guests
947.22 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $189/Night
7 Nights - US $1,321
Hotel
- Minnesota
- ·
- Montevideo
- 4.50 mi to center
9.2Exceptional
(230 Reviews)
1 Bath
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $89/Night
7 Nights - US $626
House
- South Dakota
- ·
- Big Stone City
- 5.68 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $109/Night
7 Nights - US $762
Hotel
- Minnesota
- ·
- Montevideo
- 4.94 mi to center
9.0Exceptional
(66 Reviews)
1 Bath
1550 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Child Friendly
US $86/Night
7 Nights - US $599
House
- Minnesota
- ·
- Montevideo
- 4.35 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $200/Night
7 Nights - US $1,397
Cabin
- Montevideo
- ·
- Ortonville
- 9.64 mi to center
9.6Exceptional
(25 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $175/Night
7 Nights - US $1,222
House
- Montevideo
- ·
- Ortonville
- 4.79 mi to center
8.8Fabulous
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $832
Apartment
- Montevideo
- ·
- Madison
- 1.47 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $165/Night
7 Nights - US $1,152
Instantly Bookable Vacation Homes in Madison
Over 17+ Instantly Bookable Vacation Homes in or Near Madison
Cabin
- South Dakota
- ·
- Big Stone City
- 5.83 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $259/Night
7 Nights - US $1,813
Cabin
- Montevideo
- ·
- Ortonville
- 4.94 mi to center
9.6Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $205/Night
7 Nights - US $1,432
House
- Montevideo
- ·
- Ortonville
- 5.08 mi to center
9.6Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
9 Guests
1624 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $341/Night
7 Nights - US $2,390
House
- Montevideo
- ·
- Ortonville
- 5.24 mi to center
9.0Exceptional
(41 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $244/Night
7 Nights - US $1,708
House
- South Dakota
- ·
- Gary
- 5.18 mi to center
6.0Good
(1 Review)
2 Bedrooms
1 Bath
7 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $207/Night
7 Nights - US $1,449
House
- Montevideo
- ·
- Ortonville
- 5.24 mi to center
10.0Exceptional
(31 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- 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
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $239/Night
7 Nights - US $1,670
House
- South Dakota
- ·
- Big Stone City
- 3.29 mi to center
9.8Exceptional
(25 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $201/Night
7 Nights - US $1,406
House
- Montevideo
- ·
- Ortonville
- 5.09 mi to center
8.4Excellent
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $119/Night
7 Nights - US $836
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 87 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 884 ft² of space, and are priced at an average of US $250 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.
Show more
Show less
Top Types of Ski Accommodations in Madison
| Type | Count |
|---|---|
| Vacation Homes | 44 |
| Cabin Rentals | 15 |
| Holiday Apartments | 6 |
| Cottages | 3 |
| Others | 2 |
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
- Cozy 2-bedroom cabin with WiFi, AC in serene Big Stone City
- Great Year-Round Lakeside Home by State Park, Golf, & Other Activities
- Spacious home with a large deck and ample space for beautiful sunset viewing!
- 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
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.™
- 3-bedroom cabin in peaceful Gary with cozy charm
- Big Stone Lake Access: Home w/Private Beach
- Park Inn
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 87 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.
People Also Ask
Finding the best prices in Madison
Map
