Madison Holiday Rentals
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
1 Bedroom
1 Bath
6 Guests
2000 ft²
Parking
Kitchen
Air Conditioner
Internet
US $214/Night
7 Nights - US $1,498
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
(129 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
(75 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
(38 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
(28 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $453/Night
7 Nights - US $3,172
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
Luxury Holiday Rentals in Madison
Over 79+ Luxury Holiday Rentals in or Near Madison
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 $582/Night
7 Nights - US $4,076
New
House
- Montevideo
- ·
- Ortonville
- 5.23 mi to center
4 Bedrooms
4 Baths
11 Guests
3186.12 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $577/Night
7 Nights - US $4,038
House
- Minnesota
- ·
- Chippewa County
- 15.16 mi to center
9.8Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $521/Night
7 Nights - US $3,649
New
House
- Montevideo
- ·
- Ortonville
- 5.07 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
1 Bath
7 Guests
2300 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $502/Night
7 Nights - US $3,515
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
(37 Reviews)
4 Bedrooms
2 Baths
10 Guests
2100 ft²
- Parking
Spa- Ocean View
- Balcony/Terrace
US $481/Night
7 Nights - US $3,369
Cabin
- South Dakota
- ·
- Big Stone City
- 5.83 mi to center
10.0Exceptional
(10 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $445/Night
7 Nights - US $3,112
House
- Montevideo
- ·
- Ortonville
- 5.06 mi to center
9.8Exceptional
(65 Reviews)
3 Bedrooms
2 Baths
11 Guests
2800 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $443/Night
7 Nights - US $3,100
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 $417/Night
7 Nights - US $2,919
Top-Rated Holiday Rentals with a Pool in Madison
Over 7+ The Best Private Villas and Holiday Rentals in Madison with a Pool
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 $387/Night
7 Nights - US $2,711
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 Holiday Rentals in Madison
Over 31+ Pet-Friendly Holiday Rentals in or Near Madison
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
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 $100/Night
7 Nights - US $698
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
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 $368/Night
7 Nights - US $2,577
New
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
House
- Montevideo
- ·
- Ortonville
- 8.81 mi to center
9.6Exceptional
(94 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
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 $195/Night
7 Nights - US $1,366
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 $364/Night
7 Nights - US $2,550
Large Holiday Rentals and Private Villas in Madison
Over 13+ Large Holiday Rentals and Private Villas in or Near Madison
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
New
Apartment
- South Dakota
- ·
- Gary
- 5.11 mi to center
3 Bedrooms
3 Baths
12 Guests
4000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $385/Night
7 Nights - US $2,697
New
Cabin
- South Dakota
- ·
- Big Stone City
- 2.80 mi to center
3 Bedrooms
2 Baths
11 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
- Laundry
US $272/Night
7 Nights - US $1,907
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
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
Wheelchair Accessible Holiday Homes in Madison
Over 4+ Wheelchair Accessible Holiday 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 $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 $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 Private Villas and Holiday Homes Under $200
Over 18+ Madison Private Villas and Holiday 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
- Child Friendly
Bedding/Linens
US $165/Night
7 Nights - US $1,154
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
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 $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
- 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
Instantly Bookable Holiday Homes in Madison
Over 18+ Instantly Bookable Holiday 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
(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
7 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $255/Night
7 Nights - US $1,782
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
House
- South Dakota
- ·
- Big Stone City
- 3.29 mi to center
9.8Exceptional
(25 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $201/Night
7 Nights - US $1,406
Book a Last Minute Place to Stay in Madison
About Casai's Private Villas and Holiday Rentals in Madison
Discover more than 88 vacation rentals available in Madison. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Madison.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Madison, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Madison. On average, places to stay near Madison offer 964.16 ft², with nightly prices averaging US $266.
With Casai, finding and comparing holiday rentals in Madison is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Madison
| Type | Count |
|---|---|
| Vacation Homes | 45 |
| Holiday Apartments | 8 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Madison
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Madison.
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
Casai 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 holiday rentals in Madison?
With numerous options available in Madison, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Madison:
- 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
- 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
- The 7th Street Charmer - Fully Remodeled
Which holiday homes in Madison are best for families?
If you're searching for a family-friendly holiday home in Madison, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Madison:
How many Casai.com holiday rentals are available in Madison?
As of 2026, Casai boasts over 88 properties listed in the Madison area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Madison.
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