Madison Vacation Rentals & Ski-in/Ski-out Homes
10.0
Exceptional
(210 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $201/Night
For 7 Nights US $1,409
10.0
Exceptional
(4 Reviews)
1399.31 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $176/Night
For 7 Nights US $1,232
10.0
Exceptional
(131 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Kitchen
- Parking
US $154/Night
For 7 Nights US $1,080
10.0
Exceptional
(105 Reviews)
800 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $186/Night
For 7 Nights US $1,302
10.0
Exceptional
(3 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Parking
- Child Friendly
- Security/Safety
US $177/Night
For 7 Nights US $1,239
10.0
Exceptional
(66 Reviews)
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- View
US $211/Night
For 7 Nights US $1,477
10.0
Exceptional
(64 Reviews)
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $243/Night
For 7 Nights US $1,703
10.0
Exceptional
(47 Reviews)
4 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $250/Night
For 7 Nights US $1,747
10.0
Exceptional
(27 Reviews)
1700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $217/Night
For 7 Nights US $1,521
Luxury Places to Stay in Madison
Over 173+ Luxury Places to Stay in or Near Madison
10.0
Exceptional
(1 Review)
3270 ft²
16 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $803/Night
For 7 Nights US $5,619
New
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $572/Night
For 7 Nights US $4,002
New
1614.59 ft²
14 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $522/Night
For 7 Nights US $3,655
10.0
Exceptional
(1 Review)
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $522/Night
For 7 Nights US $3,652
10.0
Exceptional
(60 Reviews)
3500 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $504/Night
For 7 Nights US $3,529
10.0
Exceptional
(7 Reviews)
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $453/Night
For 7 Nights US $3,172
10.0
Exceptional
(24 Reviews)
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
US $444/Night
For 7 Nights US $3,105
10.0
Exceptional
(2 Reviews)
3175 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $436/Night
For 7 Nights US $3,051
9.8
Exceptional
(9 Reviews)
510 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $421/Night
For 7 Nights US $2,946
Top-Rated Vacation Rentals with a Pool in Madison
Over 19+ Top-Rated Vacation Rentals with a Pool in or Near Madison
10.0
Exceptional
(66 Reviews)
2200 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $396/Night
For 7 Nights US $2,769
10.0
Exceptional
(39 Reviews)
2200 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $404/Night
For 7 Nights US $2,825
9.8
Exceptional
(84 Reviews)
900 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $218/Night
For 7 Nights US $1,523
9.4
Exceptional
(113 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $103/Night
For 7 Nights US $720
8.8
Fabulous
(688 Reviews)
1 Bathroom
Family Friendly
Hotel
- Spa
- Pool
- Balcony/Terrace
US $107/Night
For 7 Nights US $746
8.8
Fabulous
(681 Reviews)
- Madison
- Scottsburg
- 0.83 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $132/Night
For 7 Nights US $925
8.8
Fabulous
(152 Reviews)
- Madison
- Scottsburg
- 0.83 mi to center
322.92 ft²
11 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $120/Night
For 7 Nights US $839
8.7
Fabulous
(150 Reviews)
- Madison
- Scottsburg
- 1.24 mi to center
348.04 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $169/Night
For 7 Nights US $1,180
8.6
Fabulous
(1002 Reviews)
1 Bathroom
Family Friendly
Hotel
- Spa
- Fireplace/Heating
- Pool
US $173/Night
For 7 Nights US $1,210
Pet-Friendly Vacation Rentals in Madison
Over 38+ Pet-Friendly Vacation Rentals in or Near Madison
10.0
Exceptional
(25 Reviews)
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $214/Night
For 7 Nights US $1,498
10.0
Exceptional
(2 Reviews)
796.53 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Pet Friendly
- Parking
US $171/Night
For 7 Nights US $1,197
6.4
Good
(430 Reviews)
- Madison
- Scottsburg
- 1.16 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $67/Night
For 7 Nights US $468
10.0
Exceptional
(20 Reviews)
1166 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $219/Night
For 7 Nights US $1,530
10.0
Exceptional
(1 Review)
1162.5 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $288/Night
For 7 Nights US $2,014
10.0
Exceptional
(15 Reviews)
1635 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $397/Night
For 7 Nights US $2,781
10.0
Exceptional
(2 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $345/Night
For 7 Nights US $2,413
10.0
Exceptional
(2 Reviews)
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $327/Night
For 7 Nights US $2,290
10.0
Exceptional
(1 Review)
7 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $207/Night
For 7 Nights US $1,446
Large Vacation Homes & Villas in Madison
Over 12+ Large Vacation Homes & Villas in or Near Madison
10.0
Exceptional
(60 Reviews)
2040 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $228/Night
For 7 Nights US $1,597
New
2098.96 ft²
11 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Parking
US $186/Night
For 7 Nights US $1,302
New
2800 ft²
10 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $337/Night
For 7 Nights US $2,359
New
1407.92 ft²
20 Guests
5 Bedrooms
8 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $216/Night
For 7 Nights US $1,513
10.0
Exceptional
(124 Reviews)
1900 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $261/Night
For 7 Nights US $1,828
10.0
Exceptional
(41 Reviews)
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $243/Night
For 7 Nights US $1,699
9.4
Exceptional
(38 Reviews)
1200 ft²
100 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $160/Night
For 7 Nights US $1,122
10.0
Exceptional
(10 Reviews)
800 ft²
100 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $239/Night
For 7 Nights US $1,676
New
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Kitchen
- Air Conditioner
- Child Friendly
US $140/Night
For 7 Nights US $980
Wheelchair Accessible Vacation Homes in Madison
Over 13+ Wheelchair Accessible Vacation Homes in or Near Madison
10.0
Exceptional
(4 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $184/Night
For 7 Nights US $1,288
9.5
Exceptional
(211 Reviews)
520.25 ft²
9 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $211/Night
For 7 Nights US $1,479
9.8
Exceptional
(414 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $171/Night
For 7 Nights US $1,199
6.0
Good
(1 Review)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $159/Night
For 7 Nights US $1,111
8.4
Excellent
(730 Reviews)
118.4 ft²
5 Bathrooms
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $106/Night
For 7 Nights US $740
8.6
Fabulous
(988 Reviews)
- Madison
- Scottsburg
- 1.25 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $159/Night
For 7 Nights US $1,111
8.4
Excellent
(629 Reviews)
468.23 ft²
6 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $166/Night
For 7 Nights US $1,163
8.4
Excellent
(240 Reviews)
321.57 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $111/Night
For 7 Nights US $779
7.8
Very Good
(166 Reviews)
333.68 ft²
7 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Breakfast
- Parking
US $148/Night
For 7 Nights US $1,038
Madison Resorts and Airbnb Homes Under $200
Over 76+ Madison Resorts and Airbnb Homes Under $200
10.0
Exceptional
(21 Reviews)
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
US $162/Night
For 7 Nights US $1,131
8.7
Fabulous
(4 Reviews)
1603.82 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Hot Tub
- Parking
- Air Conditioner
US $179/Night
For 7 Nights US $1,253
8.8
Fabulous
(574 Reviews)
- Madison
- Scottsburg
- 0.63 mi to center
1 Bathroom
Family Friendly
Hotel
- Breakfast
- Kitchen
- Parking
US $84/Night
For 7 Nights US $588
10.0
Exceptional
(11 Reviews)
2000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $171/Night
For 7 Nights US $1,197
5.0
Average
(1 Review)
1194.79 ft²
6 Guests
2 Bedrooms
1 Bathroom
House
- Spa
- Fireplace/Heating
- Pet Friendly
US $159/Night
For 7 Nights US $1,113
10.0
Exceptional
(11 Reviews)
300 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $118/Night
For 7 Nights US $826
10.0
Exceptional
(9 Reviews)
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $156/Night
For 7 Nights US $1,090
10.0
Exceptional
(2 Reviews)
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $168/Night
For 7 Nights US $1,179
10.0
Exceptional
(1 Review)
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $183/Night
For 7 Nights US $1,283
Instantly Bookable Vacation Homes in Madison
Over 74+ Instantly Bookable Vacation Homes in or Near Madison
10.0
Exceptional
(17 Reviews)
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $282/Night
For 7 Nights US $1,972
New
1 Bedroom
1 Bathroom
Family Friendly
House
- Child Friendly
US $119/Night
For 7 Nights US $834
10.0
Exceptional
(6 Reviews)
680 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $420/Night
For 7 Nights US $2,938
10.0
Exceptional
(2 Reviews)
2000 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $338/Night
For 7 Nights US $2,365
9.8
Exceptional
(49 Reviews)
950 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $224/Night
For 7 Nights US $1,570
9.8
Exceptional
(32 Reviews)
1556 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $264/Night
For 7 Nights US $1,848
9.8
Exceptional
(7 Reviews)
325 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $176/Night
For 7 Nights US $1,231
9.8
Exceptional
(7 Reviews)
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $159/Night
For 7 Nights US $1,114
9.6
Exceptional
(21 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $290/Night
For 7 Nights US $2,029
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 182 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 545.79 ft² of space, and are priced at an average of US $217 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 | 101 |
| Holiday Apartments | 26 |
| Cabin Rentals | 12 |
| Cottages | 4 |
| B&B | 1 |
| 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, 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
- #209 Kings, River View, Deck, Bicentennial Park
- Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
- The Wadsworth in National Historic District of Madison, Indiana.
- Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
- Rustic cabin just outside of Madison!
- Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
How many vacation rentals have private pools in Madison?
Uncover 1 vacation rentals boasting private pools near Madison. Explore top-rated RBO homes offering access to a swimming pool:
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 182 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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Finding the best prices in Madison
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