Madison, IN Vacation Rentals & Ski-in/Ski-out Homes
Cabin
10.0Exceptional
(31 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
Parking
Kitchen
Air Conditioner
Internet
US $185/Night
7 Nights - US $1,292
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Hot Tub- Parking
Balcony/Terrace- Air Conditioner
US $381/Night
7 Nights - US $2,668
House
9.2Exceptional
(168 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
US $123/Night
7 Nights - US $860
House
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $164/Night
7 Nights - US $1,147
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Child Friendly
Security/Safety
US $177/Night
7 Nights - US $1,239
Cabin
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Cabin
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Cabin
9.8Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $230/Night
7 Nights - US $1,610
Cabin
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Luxury Places to Stay in Madison
Over 191+ Luxury Places to Stay in or Near Madison
House
10.0Exceptional
(3 Reviews)
5 Bedrooms
4 Baths
16 Guests
3270 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $754/Night
7 Nights - US $5,278
House
4 Bedrooms
4 Baths
14 Guests
1614.59 ft²
- Air Conditioner
- Internet
- Child Friendly
Sports/Activities
US $647/Night
7 Nights - US $4,532
House
9.8Exceptional
(29 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $628/Night
7 Nights - US $4,396
Cabin
9.4Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
14 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $620/Night
7 Nights - US $4,342
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $615/Night
7 Nights - US $4,303
House
10.0Exceptional
(67 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $558/Night
7 Nights - US $3,908
House
9.6Exceptional
(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $507/Night
7 Nights - US $3,550
House
10.0Exceptional
(46 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $496/Night
7 Nights - US $3,469
House
10.0Exceptional
(72 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $491/Night
7 Nights - US $3,437
Top-Rated Vacation Rentals with a Pool in Madison
Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Madison
House
10.0Exceptional
(91 Reviews)
2 Bedrooms
2 Baths
4 Guests
900 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $232/Night
7 Nights - US $1,626
Hotel
- Madison
- ·
- Scottsburg
- 1.24 mi to center
8.9Fabulous
(189 Reviews)
1 Bath
348.04 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $117/Night
7 Nights - US $819
Hotel
8.7Fabulous
(328 Reviews)
11 Baths
172.22 ft²
- Parking
- Pool
- Balcony/Terrace
View
US $95/Night
7 Nights - US $664
Hotel
8.4Excellent
(655 Reviews)
6 Baths
468.23 ft²
- Private Pool
- Breakfast
EV Charge Station- Parking
US $180/Night
7 Nights - US $1,260
Hotel
8.3Excellent
(264 Reviews)
1 Bath
321.57 ft²
- Private Pool
- Breakfast
- EV Charge Station
- Parking
US $104/Night
7 Nights - US $728
Hotel
7.1Very Good
(271 Reviews)
1 Bath
21.53 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
US $77/Night
7 Nights - US $540
Hotel
6.8Good
(569 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $91/Night
7 Nights - US $636
Hotel
- Madison
- ·
- Scottsburg
- 0.91 mi to center
6.0Good
(255 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Air Conditioner
US $78/Night
7 Nights - US $549
House
3.0Average
(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,015
Pet-Friendly Vacation Rentals in Madison
Over 41+ Pet-Friendly Vacation Rentals in or Near Madison
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $165/Night
7 Nights - US $1,152
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Parking
Spa- Balcony/Terrace
- Internet
US $171/Night
7 Nights - US $1,197
Hotel
- Madison
- ·
- Scottsburg
- 1.16 mi to center
6.4Good
(458 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $73/Night
7 Nights - US $511
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,560
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1162.5 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $208/Night
7 Nights - US $1,458
House
9.6Exceptional
(47 Reviews)
3 Bedrooms
2 Baths
7 Guests
1650 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $234/Night
7 Nights - US $1,635
House
10.0Exceptional
(35 Reviews)
3 Bedrooms
1 Bath
8 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $355/Night
7 Nights - US $2,485
House
10.0Exceptional
(21 Reviews)
4 Bedrooms
2 Baths
8 Guests
2900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $390/Night
7 Nights - US $2,729
House
9.8Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
8 Guests
1635 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $390/Night
7 Nights - US $2,730
Large Vacation Homes & Villas in Madison
Over 14+ Large Vacation Homes & Villas in or Near Madison
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
4 Baths
10 Guests
2800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $360/Night
7 Nights - US $2,523
Apartment
6.5Good
(2 Reviews)
5 Bedrooms
8 Baths
20 Guests
1407.92 ft²
- Parking
- Air Conditioner
- Internet
Bedding/Linens
US $238/Night
7 Nights - US $1,665
Cabin
9.4Exceptional
(40 Reviews)
2 Bedrooms
1 Bath
100 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $246/Night
7 Nights - US $1,725
House
3 Bedrooms
3 Baths
11 Guests
2098.96 ft²
- Parking
- Spa
- Balcony/Terrace
- Internet
US $186/Night
7 Nights - US $1,302
Cabin
10.0Exceptional
(73 Reviews)
4 Bedrooms
2 Baths
12 Guests
2040 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $294/Night
7 Nights - US $2,061
Cabin
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $431/Night
7 Nights - US $3,015
Cabin
10.0Exceptional
(56 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,882
House
10.0Exceptional
(133 Reviews)
6 Bedrooms
2 Baths
12 Guests
1900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $278/Night
7 Nights - US $1,944
New
House
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $300/Night
7 Nights - US $2,097
Wheelchair Accessible Vacation Homes in Madison
Over 7+ Wheelchair Accessible Vacation Homes in or Near Madison
Hotel
9.5Exceptional
(196 Reviews)
7 Baths
518.2 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Kitchen
US $208/Night
7 Nights - US $1,456
Hotel
9.8Exceptional
(465 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $185/Night
7 Nights - US $1,292
Hotel
8.4Excellent
(689 Reviews)
5 Baths
118.4 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $116/Night
7 Nights - US $813
Hotel
7.6Very Good
(140 Reviews)
7 Baths
333.68 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $700
Hotel
7.4Very Good
(118 Reviews)
7 Baths
333.68 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $92/Night
7 Nights - US $645
Hotel
6.9Good
(113 Reviews)
5 Baths
269.1 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $71/Night
7 Nights - US $497
Hotel
- Madison
- ·
- Scottsburg
- 1.23 mi to center
5.9Average
(73 Reviews)
4 Baths
269.1 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $65/Night
7 Nights - US $457
Madison Resorts and Airbnb Homes Under $200
Over 59+ Madison Resorts and Airbnb Homes Under $200
Cottage
9.8Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,279
House
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
4 Guests
699.65 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $141/Night
7 Nights - US $986
Hotel
8.8Fabulous
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $102/Night
7 Nights - US $717
House
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
US $146/Night
7 Nights - US $1,019
House
6.0Good
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1205.56 ft²
- Parking
- Spa
- Balcony/Terrace
- Internet
US $190/Night
7 Nights - US $1,332
RV Rental
1 Bedroom
1 Bath
2 Guests
Designated Smoking Area
US $50/Night
7 Nights - US $353
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
350 ft²
- Parking
- Kitchen
- Air Conditioner
- Laundry
US $121/Night
7 Nights - US $849
Apartment
9.8Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Parking
- Kitchen
- Air Conditioner
- Laundry
US $115/Night
7 Nights - US $805
Apartment
9.8Exceptional
(7 Reviews)
1 Bedroom
1 Bath
3 Guests
325 ft²
- Parking
- Kitchen
- Air Conditioner
- Laundry
US $117/Night
7 Nights - US $820
Instantly Bookable Vacation Homes in Madison
Over 87+ Instantly Bookable Vacation Homes in or Near Madison
House
9.4Exceptional
(20 Reviews)
1 Bedroom
1 Bath
4 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $224/Night
7 Nights - US $1,569
House
1 Bedroom
1 Bath
- Child Friendly
US $119/Night
7 Nights - US $834
House
2 Bedrooms
2 Baths
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $218/Night
7 Nights - US $1,525
House
9.8Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
8 Guests
1300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $308/Night
7 Nights - US $2,157
House
9.6Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $391/Night
7 Nights - US $2,737
House
9.4Exceptional
(30 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $332/Night
7 Nights - US $2,326
House
9.2Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $472/Night
7 Nights - US $3,305
New
Apartment
10.0Exceptional
(28 Reviews)
3 Bedrooms
2 Baths
5 Guests
1800 ft²
- Hot Tub
- Parking
- View
- Kitchen
US $411/Night
7 Nights - US $2,878
New
House
10.0Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $398/Night
7 Nights - US $2,789
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 200 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 580.2 ft² of space, and are priced at an average of US $241 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 | 116 |
| Holiday Apartments | 32 |
| Cabin Rentals | 15 |
| Cottages | 5 |
| B&B | 1 |
| Others | 1 |
| Unique Vacation Rentals | 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, IN
View the weather forecast for Madison before booking your Madison Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Madison, IN
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, IN
Complexes around Madison, IN
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.
- 1800’s restored log cabin on 26 private rolling wooded acres with sunset views
- The Chandler Hotel
- Secluded Country Home in Historic Hoosier Hills
- Stoney Creek - Sit back and unwind
- Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
- Red comfy cottage
- The Wadsworth in National Historic District of Madison, Indiana.
- Rustic cabin just outside of Madison!
- #209 Kings, River View, Deck, Bicentennial Park
- Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
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 200 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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