Madison Vacation Rentals & Ski-in/Ski-out Homes
Cabin
10.0Exceptional
(225 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Ocean View
Balcony/Terrace
View
US $206/Night
7 Nights - US $1,445
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1603.82 ft²
Hot Tub- Parking
- Balcony/Terrace
Air Conditioner
US $243/Night
7 Nights - US $1,700
House
9.4Exceptional
(148 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
US $152/Night
7 Nights - US $1,063
Cabin
10.0Exceptional
(124 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $207/Night
7 Nights - US $1,446
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Child Friendly
Security/Safety
US $177/Night
7 Nights - US $1,239
Apartment
10.0Exceptional
(88 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Parking
- Ocean View
- View
Kitchen
US $219/Night
7 Nights - US $1,534
House
10.0Exceptional
(76 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,061
House
10.0Exceptional
(47 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Breakfast
- Parking
- Ocean View
US $288/Night
7 Nights - US $2,013
Apartment
10.0Exceptional
(44 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $211/Night
7 Nights - US $1,474
Luxury Places to Stay in Madison
Over 183+ Luxury Places to Stay in or Near Madison
Cabin
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $821/Night
7 Nights - US $5,750
House
9.4Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $752/Night
7 Nights - US $5,265
House
9.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $749/Night
7 Nights - US $5,241
House
4 Bedrooms
4 Baths
14 Guests
1614.59 ft²
- Air Conditioner
- Internet
Sports/Activities- Security/Safety
US $730/Night
7 Nights - US $5,111
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
3270 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $728/Night
7 Nights - US $5,097
Cabin
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
14 Guests
1617 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $639/Night
7 Nights - US $4,476
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $607/Night
7 Nights - US $4,250
House
10.0Exceptional
(64 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $554/Night
7 Nights - US $3,876
House
9.4Exceptional
(31 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $507/Night
7 Nights - US $3,550
Top-Rated Vacation Rentals with a Pool in Madison
Over 11+ Top-Rated Vacation Rentals with a Pool in or Near Madison
House
10.0Exceptional
(71 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $406/Night
7 Nights - US $2,841
House
10.0Exceptional
(43 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $405/Night
7 Nights - US $2,833
House
9.8Exceptional
(86 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $233/Night
7 Nights - US $1,630
Hotel
- Madison
- ·
- Scottsburg
- 1.24 mi to center
8.8Fabulous
(162 Reviews)
1 Bath
348.04 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $122/Night
7 Nights - US $855
Hotel
8.7Fabulous
(328 Reviews)
11 Baths
172.22 ft²
Oceanfront- Parking
- Pool
- Ocean View
US $140/Night
7 Nights - US $980
Hotel
8.4Excellent
(644 Reviews)
6 Baths
468.23 ft²
- Private Pool
- Breakfast
EV Charge Station- Parking
US $116/Night
7 Nights - US $813
Hotel
8.3Excellent
(246 Reviews)
1 Bath
321.57 ft²
- Private Pool
- Breakfast
- EV Charge Station
- Parking
US $111/Night
7 Nights - US $779
Hotel
7.0Very Good
(277 Reviews)
1 Bath
21.53 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $79/Night
7 Nights - US $553
Hotel
6.8Good
(559 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $91/Night
7 Nights - US $636
Pet-Friendly Vacation Rentals in Madison
Over 40+ Pet-Friendly Vacation Rentals in or Near Madison
House
10.0Exceptional
(30 Reviews)
2 Bedrooms
1 Bath
4 Guests
1166 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $258/Night
7 Nights - US $1,803
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
(449 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $79/Night
7 Nights - US $556
House
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
8 Guests
1635 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $372/Night
7 Nights - US $2,602
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
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $364/Night
7 Nights - US $2,548
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,170
House
9.8Exceptional
(67 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $213/Night
7 Nights - US $1,489
Cottage
9.6Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
486 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $197/Night
7 Nights - US $1,381
Large Vacation Homes & Villas in Madison
Over 13+ Large Vacation Homes & Villas in or Near Madison
Cabin
10.0Exceptional
(67 Reviews)
4 Bedrooms
2 Baths
12 Guests
2040 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $258/Night
7 Nights - US $1,807
Apartment
6.5Good
(2 Reviews)
5 Bedrooms
8 Baths
20 Guests
1407.92 ft²
- Parking
- Air Conditioner
- Internet
Laundry
US $216/Night
7 Nights - US $1,513
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
4 Baths
10 Guests
2800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $355/Night
7 Nights - US $2,483
House
3 Bedrooms
3 Baths
11 Guests
2098.96 ft²
- Parking
- Spa
- Balcony/Terrace
- Internet
US $186/Night
7 Nights - US $1,302
House
9.8Exceptional
(21 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $475/Night
7 Nights - US $3,325
House
10.0Exceptional
(127 Reviews)
6 Bedrooms
2 Baths
12 Guests
1900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $274/Night
7 Nights - US $1,918
Cabin
10.0Exceptional
(49 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $268/Night
7 Nights - US $1,876
New
Cabin
9.4Exceptional
(39 Reviews)
2 Bedrooms
1 Bath
100 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,717
Cottage
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
100 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $239/Night
7 Nights - US $1,676
Wheelchair Accessible Vacation Homes in Madison
Over 9+ Wheelchair Accessible Vacation Homes in or Near Madison
Hotel
10.0Exceptional
(4 Reviews)
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $184/Night
7 Nights - US $1,288
Hotel
9.5Exceptional
(196 Reviews)
7 Baths
518.2 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Kitchen
US $202/Night
7 Nights - US $1,412
Hotel
9.8Exceptional
(436 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $171/Night
7 Nights - US $1,199
Hotel
6.0Good
(1 Review)
1 Bath
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,111
Hotel
8.4Excellent
(689 Reviews)
5 Baths
118.4 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $116/Night
7 Nights - US $813
Hotel
7.7Very Good
(152 Reviews)
7 Baths
333.68 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $115/Night
7 Nights - US $807
Hotel
7.6Very Good
(113 Reviews)
7 Baths
333.68 ft²
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $64/Night
7 Nights - US $447
Hotel
6.9Good
(113 Reviews)
5 Baths
269.1 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $74/Night
7 Nights - US $516
Hotel
- Madison
- ·
- Scottsburg
- 1.23 mi to center
5.9Average
(73 Reviews)
4 Baths
269.1 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $70/Night
7 Nights - US $490
Madison Resorts and Airbnb Homes Under $200
Over 71+ Madison Resorts and Airbnb Homes Under $200
House
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $195/Night
7 Nights - US $1,365
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
Hotel
- Madison
- ·
- Scottsburg
- 0.63 mi to center
8.8Fabulous
(638 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $83/Night
7 Nights - US $581
House
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
New
Apartment
1 Bedroom
1 Bath
6 Guests
1603.82 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $129/Night
7 Nights - US $906
Cabin
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Apartment
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Parking
- Kitchen
- Air Conditioner
- Laundry
US $144/Night
7 Nights - US $1,008
Cabin
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $168/Night
7 Nights - US $1,179
Instantly Bookable Vacation Homes in Madison
Over 79+ Instantly Bookable Vacation Homes in or Near Madison
House
10.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,254
House
1 Bedroom
1 Bath
- Child Friendly
US $119/Night
7 Nights - US $834
House
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $251/Night
7 Nights - US $1,759
House
10.0Exceptional
(11 Reviews)
2 Bedrooms
4 Baths
6 Guests
2000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $418/Night
7 Nights - US $2,929
New
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,173
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
1625 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $254/Night
7 Nights - US $1,779
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
350 ft²
- Parking
- Kitchen
- Air Conditioner
- Laundry
US $142/Night
7 Nights - US $996
House
9.8Exceptional
(69 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,731
House
9.8Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1556 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,113
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 192 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 571.51 ft² of space, and are priced at an average of US $239 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 | 110 |
| Holiday Apartments | 32 |
| Cabin Rentals | 14 |
| Cottages | 4 |
| 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…
- The Wadsworth in National Historic District of Madison, Indiana.
- #209 Kings, River View, Deck, Bicentennial Park
- Rustic cabin just outside of Madison!
- Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
- Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
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.™
- Beautiful townhome just steps from Historical Downtown Madison
- Beautiful Bungalow on Main
- Hillside 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 192 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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