Madison Holiday Rentals
Cabin
10.0Exceptional
(118 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
Hot Tub
Fireplace/Heating
Ocean View
Balcony/Terrace
US $192/Night
7 Nights - US $1,342
House
10.0Exceptional
(4 Reviews)
1 Bedroom
2 Baths
6 Guests
1399.31 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Parking
US $176/Night
7 Nights - US $1,232
Hotel
7.0Very Good
(546 Reviews)
1 Bath
Pool- Balcony/Terrace
Kitchen- Parking
US $91/Night
7 Nights - US $636
Apartment
10.0Exceptional
(79 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
View- Kitchen
US $225/Night
7 Nights - US $1,578
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Child Friendly
Security/Safety
US $177/Night
7 Nights - US $1,239
House
10.0Exceptional
(68 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $246/Night
7 Nights - US $1,723
House
10.0Exceptional
(47 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $258/Night
7 Nights - US $1,804
Apartment
10.0Exceptional
(37 Reviews)
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $164/Night
7 Nights - US $1,151
House
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $217/Night
7 Nights - US $1,521
Luxury Holiday Rentals in Madison
Over 174+ Luxury Holiday Rentals in or Near Madison
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
3270 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $874/Night
7 Nights - US $6,117
House
8.8Fabulous
(4 Reviews)
1 Bedroom
2 Baths
6 Guests
1603.82 ft²
- Hot Tub
- Parking
Air Conditioner
Internet
US $749/Night
7 Nights - US $5,241
New
House
4 Bedrooms
4 Baths
14 Guests
1614.59 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $730/Night
7 Nights - US $5,111
New
Cabin
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1617 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $568/Night
7 Nights - US $3,973
Cabin
4 Bedrooms
3 Baths
14 Guests
1617 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $542/Night
7 Nights - US $3,795
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $522/Night
7 Nights - US $3,652
House
10.0Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $436/Night
7 Nights - US $3,049
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
3175 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $432/Night
7 Nights - US $3,022
House
9.4Exceptional
(29 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $431/Night
7 Nights - US $3,019
Top-Rated Holiday Rentals with a Pool in Madison
Over 14+ The Best Private Villas and Holiday Rentals in Madison with a Pool
House
10.0Exceptional
(69 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $342/Night
7 Nights - US $2,393
House
10.0Exceptional
(41 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $359/Night
7 Nights - US $2,511
House
9.8Exceptional
(84 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $215/Night
7 Nights - US $1,503
Hotel
- Madison
- ·
- Scottsburg
- 1.24 mi to center
8.8Fabulous
(162 Reviews)
1 Bath
348.04 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $154/Night
7 Nights - US $1,078
Hotel
8.7Fabulous
(328 Reviews)
11 Baths
172.22 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $140/Night
7 Nights - US $980
Hotel
- Madison
- ·
- Scottsburg
- 0.83 mi to center
8.7Fabulous
(154 Reviews)
11 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $120/Night
7 Nights - US $839
Hotel
8.3Excellent
(620 Reviews)
6 Baths
468.23 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $116/Night
7 Nights - US $813
Hotel
8.3Excellent
(246 Reviews)
1 Bath
321.57 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $111/Night
7 Nights - US $779
Hotel
7.0Very Good
(277 Reviews)
1 Bath
21.53 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $86/Night
7 Nights - US $600
Pet-Friendly Holiday Rentals in Madison
Over 39+ Pet-Friendly Holiday Rentals in or Near Madison
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
Spa- Balcony/Terrace
- Pet Friendly
- Parking
US $171/Night
7 Nights - US $1,197
House
10.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
1166 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $205/Night
7 Nights - US $1,436
Hotel
- Madison
- ·
- Scottsburg
- 1.16 mi to center
6.4Good
(445 Reviews)
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $74/Night
7 Nights - US $520
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1162.5 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $288/Night
7 Nights - US $2,014
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $340/Night
7 Nights - US $2,382
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $290/Night
7 Nights - US $2,032
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $207/Night
7 Nights - US $1,446
House
9.8Exceptional
(66 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $181/Night
7 Nights - US $1,270
Cottage
9.4Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
486 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
US $207/Night
7 Nights - US $1,449
Large Holiday Rentals and Private Villas in Madison
Over 13+ Large Holiday Rentals and Private Villas in or Near Madison
Apartment
6.5Good
(2 Reviews)
5 Bedrooms
8 Baths
20 Guests
1407.92 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,513
Cabin
10.0Exceptional
(65 Reviews)
4 Bedrooms
2 Baths
12 Guests
2040 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $258/Night
7 Nights - US $1,803
House
3 Bedrooms
3 Baths
11 Guests
2098.96 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $186/Night
7 Nights - US $1,302
House
3 Bedrooms
4 Baths
10 Guests
2800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $348/Night
7 Nights - US $2,439
House
10.0Exceptional
(125 Reviews)
6 Bedrooms
2 Baths
12 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $287/Night
7 Nights - US $2,007
Cabin
10.0Exceptional
(44 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $218/Night
7 Nights - US $1,523
Cottage
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
100 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $239/Night
7 Nights - US $1,676
Other
3 Bedrooms
2 Baths
10 Guests
- Kitchen
- Air Conditioner
- Child Friendly
Laundry
US $140/Night
7 Nights - US $980
House
10.0Exceptional
(61 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $504/Night
7 Nights - US $3,531
Wheelchair Accessible Holiday Homes in Madison
Over 10+ Wheelchair Accessible Holiday Homes in or Near Madison
Hotel
9.5Exceptional
(214 Reviews)
8 Baths
509.94 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $211/Night
7 Nights - US $1,479
Hotel
10.0Exceptional
(4 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $184/Night
7 Nights - US $1,288
Hotel
9.8Exceptional
(426 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $194/Night
7 Nights - US $1,360
Hotel
8.4Excellent
(689 Reviews)
5 Baths
118.4 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $106/Night
7 Nights - US $740
Hotel
6.0Good
(1 Review)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,111
Hotel
- Madison
- ·
- Scottsburg
- 1.25 mi to center
8.6Fabulous
(1004 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $132/Night
7 Nights - US $923
Hotel
7.9Very Good
(164 Reviews)
7 Baths
333.68 ft²
- Fireplace/Heating
- Breakfast
- Parking
- Air Conditioner
US $117/Night
7 Nights - US $817
Hotel
7.7Very Good
(117 Reviews)
7 Baths
333.68 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $83/Night
7 Nights - US $580
Hotel
6.9Good
(113 Reviews)
5 Baths
269.1 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $82/Night
7 Nights - US $571
Madison Private Villas and Holiday Homes Under $200
Over 70+ Madison Private Villas and Holiday Homes Under $200
House
6.0Good
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1205.56 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $190/Night
7 Nights - US $1,332
Cabin
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,316
House
1 Bedroom
1 Bath
- Child Friendly
US $119/Night
7 Nights - US $834
House
2 Bedrooms
1 Bath
2 Guests
204.51 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Child Friendly
US $83/Night
7 Nights - US $583
House
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $173/Night
7 Nights - US $1,211
Apartment
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $144/Night
7 Nights - US $1,008
Cabin
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $173/Night
7 Nights - US $1,211
Cabin
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $173/Night
7 Nights - US $1,211
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $167/Night
7 Nights - US $1,171
Instantly Bookable Holiday Homes in Madison
Over 77+ Instantly Bookable Holiday Homes in or Near Madison
Cabin
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $200/Night
7 Nights - US $1,401
House
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $274/Night
7 Nights - US $1,919
House
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,538
House
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $263/Night
7 Nights - US $1,843
Apartment
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
680 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $293/Night
7 Nights - US $2,052
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
350 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $159/Night
7 Nights - US $1,112
House
9.8Exceptional
(62 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $183/Night
7 Nights - US $1,281
House
9.8Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
1556 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $270/Night
7 Nights - US $1,892
House
9.8Exceptional
(8 Reviews)
2 Bedrooms
4 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $340/Night
7 Nights - US $2,380
Book a Last Minute Place to Stay in Madison
About Casai's Private Villas and Holiday Rentals in Madison
Discover more than 183 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 567.13 ft², with nightly prices averaging US $224.
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 | 104 |
| Holiday Apartments | 28 |
| Cottages | 4 |
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, 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
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, IN
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:
- Secluded Country Home in Historic Hoosier Hills
- Stoney Creek - Sit back and unwind
- Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
- #209 Kings, River View, Deck, Bicentennial Park
- The Wadsworth in National Historic District of Madison, Indiana.
- Rustic cabin just outside of Madison!
- Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
- The Cypress Grove Inn ~Madison, IN! *5 Star hosts!
- Carol’s Cabin in the Woods in Historic Hoosier Hills
- #207 King Suites, River Views, Deck, Downtown
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:
- Beautiful Bungalow on Main
- Historic Row House in the heart of downtown Madison
- Riverboat Inn and Suites
How many Casai.com holiday rentals are available in Madison?
As of 2026, Casai boasts over 183 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.
People Also Ask
Finding the best prices in Madison
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