Yn Travel - Vacation Rentals in Madison

Secluded Country Home in Historic Hoosier Hills From US $261
         

10.0 (124 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Madison Manor II by the River Hot Tub Downtown From US $176
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Chandler Hotel From US $154
         

10.0 (131 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Stoney Creek - Sit back and unwind From US $186
         

10.0 (105 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Designated Smoking Area
#209 Kings, River View, Deck, Bicentennial Park From US $396
         

10.0 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Madison

Over 172+ Luxury Places to Stay in or Near Madison
The Aviator: Serene Ambience & Stylish Comfort From US $572
         

Spacious family cabin with game room and backyard From US $522
         

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New
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Alterra:Slees 8,Steps to Main St,Serene From US $522
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
East Main Lofts - Coastal 201 From US $421
         

9.8 (9 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Madison

Over 18+ Top-Rated Vacation Rentals with a Pool in or Near Madison
#207 King Suites, River Views, Deck, Downtown From US $404
         

10.0 (39 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Red comfy cottage From US $218
         

9.8 (84 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Riverboat Inn and Suites From US $103
         

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9.4 (113 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn Madison near Clifty Falls From US $107
         

8.8 (688 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express & Suites Scottsburg by IHG From US $132
         

8.8 (681 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express Scottsburg by IHG From US $120
         

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8.8 (152 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Belterra Casino Resort From US $173
         

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8.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn & Suites Scottsburg From US $159
         

8.6 (988 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Madison

Over 38+ Pet-Friendly Vacation Rentals in or Near Madison
East End River Retreat Dogs Welcome! From US $288
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Accessibility
Red Roof Inn Scottsburg From US $67
         

6.4 (430 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Carol’s Cabin in the Woods in Historic Hoosier Hills From US $243
         

10.0 (41 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
The Nature House is a perfect mix of charm and location! From US $347
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining From US $214
         

East End River Retreat: Dogs Welcome! From US $219
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Madison on PetFriendly.io

Large Vacation Homes & Villas in Madison

Over 10+ Large Vacation Homes & Villas in or Near Madison
Rustic cabin just outside of Madison! From US $228
         

10.0 (60 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Designated Smoking Area
East Main Lofts From US $216
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
'The Bovard Lodge' Rustic Cabin Near Ohio River! From US $160
         

9.4 (38 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Pine Lodge at Lost Trails From US $337
         

New
House
  • Air Conditioner
  • Parking
  • TV
Renovated Craftsman House w/Patio & Fire Pit! From US $377
         

10.0 (49 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Historic Madison Retreat - 1 Mi to Ohio River From US $239
         

10.0 (10 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
East Main Lofts -Roller Rink 301 From US $980
         

10.0 (7 Reviews)
Apartment
  • Security/Safety
  • Child Friendly
The Hacienda. Sprawling Ranch Home From US $461
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Madison

Over 13+ Wheelchair Accessible Vacation Homes in or Near Madison
La Belle Rivière Suite 202 at The Chandler Hotel From US $184
         

10.0 (4 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill From US $211
         

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9.5 (211 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill From US $171
         

The Stablemans Quarters 206 at The Chandler Hotel From US $159
         

6.0 (1 Review)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Hampton Inn & Suites Scottsburg From US $169
         

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8.6 (146 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hillside Inn From US $106
         

8.4 (730 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Clifty Inn From US $166
         

8.4 (629 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn Madison near Clifty Falls From US $111
         

8.4 (240 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Madison Vacation Rentals and Airbnb Places to Stay Under $200

Over 77+ Madison Vacation Rentals and Airbnb Places to Stay Under $200
Cedar Rustic Cabin at Lost Trails From US $162
         

10.0 (21 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
East Main Lofts - Coastal 201 From US $177
         

10.0 (3 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
Hometowne Inn & Suites From US $84
         

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8.8 (574 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Modern cabin very close to scenic riverfront walks From US $171
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Maple Cozy Cabin at Lost Trails From US $156
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Walnut Secluded Cabin at Lost Trails From US $168
         

10.0 (2 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Mulberry Secluded Cabin at Lost Trails From US $183
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Madison

Over 71+ Instantly Bookable Vacation Homes in or Near Madison
The Cypress Grove Inn ~Madison, IN! *5 Star hosts! From US $250
         

10.0 (47 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Artist’s A-Frame From US $217
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Enchanted Cottage From US $243
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • View
  • Ocean View

About Madison Vacation Rentals

With more than 181 Madison vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Yntravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Madison.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Yntravel Madison, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Madison. Places to stay near Madison are 548.8 ft² on average, with prices averaging $216 a night.

Yntravel makes it easy and safe to find and compare vacation rentals in Madison with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Madison

Type Count
Vacation Homes 99
Hotels with Suites 37
Holiday Apartments 26
Cabin Rentals 12
Cottages 4
Others 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Madison

Pro Tip: Yntravel makes it easy to compare the best listings on Yntravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Yntravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Madison.

Weather in Madison

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

Madison Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Madison?
How many vacation rentals have private pools in Madison?

There are 1 vacation rentals with private pools near Madison. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Madison?

Currently, the total number of properties listed in 2026 is over 181 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.