Photo by D.D.Oakley

Madison holiday lettings

We found 78 holiday rentals — enter your dates for availability

Discover a selection of 39 homes, 17 apartments and other holiday rentals in Madison that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and cable TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Madison

Showing deals for:21 Nov - 28 Nov

Image gallery for Cozy Cabin Madison Indiana

Exterior
10 out of 10 rating
Exceptional
(16 reviews)

Cozy Cabin Madison Indiana

Milton, KY

8% off
Price is £1,175
£168 per night
includes taxes & fees
Cozy Cabin Madison Indiana

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Madison

Find out more about Madison

Delight in the riverfront landscape of Madison

The area's history and festivals are just some of the reasons to come on holiday to Madison. This city's casino gaming, riverfront and shopping draw many visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Madison

Are you hoping to find attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Madison a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lanthier Winery (0.4 mi / 0.7 km)
  • Stream Cliff Herb Farm and Winery (16.1 mi / 25.9 km)
  • The Ridge Winery Tasting Room (20.3 mi / 32.7 km)
  • Kentucky Speedway (24.9 mi / 40 km)
  • Thomas Family Winery (0.1 mi / 0.2 km)
  • Westwood Golf Course (23 mi / 37 km)

Exploring the natural landscape of Madison

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Madison is a great place to get outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • General Butler State Resort Park (12.9 mi / 20.8 km)
  • Muscatatuck National Wildlife Refuge (26.7 mi / 43 km)
  • Vevay Island (18.3 mi / 29.5 km)
  • Linza Graham Park (21 mi / 33.9 km)
  • Lake Iola Park (21.5 mi / 34.6 km)
  • Muscatatuck County Park (22.8 mi / 36.7 km)

Transport options to and around Madison

Fly into Louisville International Airport (SDF), the closest airport, located 42.7 mi (68.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Cincinnati-Northern Kentucky Int'l Airport (CVG), which is 44.7 mi (71.9 km) away.

Frequently asked questions

What is the best area to stay in Madison when booking a holiday rental?
When considering a holiday rental in Madison, Indiana, one of the most appealing areas to stay is the historic downtown district. This charming neighbourhood is filled with beautifully preserved 19th-century architecture and offers a vibrant atmosphere with plenty of shops, cafes, and restaurants. Staying here puts you within walking distance of the iconic Lanthier Winery, where you can enjoy tastings and scenic views, as well as the fascinating Madison Museum of Fine Arts, which showcases local art and history.

Another wonderful option is the riverfront area, which boasts stunning views of the Ohio River. This picturesque setting is superb for leisurely strolls along the waterfront and provides easy access to the scenic Clifty Falls State Park, known for its beautiful hiking trails and waterfalls. The riverfront area typically has a good selection of holiday rentals, allowing visitors to choose from quaint cottages to larger homes, suiting various group sizes.
How much does it cost to rent a holiday home in Madison?
Prices for holiday rentals in Madison vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Madison to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Madison holiday house rentals?
You can find great discounts on house rentals in Madison on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday houses are the most popular type of rental accommodation, with approximately 35 available throughout the area. These houses are often situated in family-friendly neighbourhoods, providing ample space and a homely atmosphere. Most holiday houses feature multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups seeking a relaxing getaway. Additionally, there are around 15 apartments for those looking for a more compact option, often located near the town centre and local attractions. For those who prefer a more rustic experience, several cabins and cottages can also be found, offering unique charm and a connection to nature.
Are there any family house rentals in Madison?
In Madison, Indiana, there are numerous family-friendly holiday rentals available—specifically, around 34 options throughout the area. The town is known for its charming historic districts and proximity to outdoor activities, making it an excellent choice for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.
Can I rent a holiday home with a pool or hot tub in Madison?
In Madison, Indiana, there are several holiday homes available for rent that feature pools and hot tubs, providing a refreshing option for travellers looking to relax. The picturesque town, known for its historic charm and scenic riverfront, offers a range of properties suitable for families or groups. Many of these rentals come equipped with private pools, hot tubs, and outdoor spaces, allowing guests to enjoy the serene surroundings.
Can I find long-stay holiday rentals in Madison?
A long-stay holiday rental in Madison is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Madison?
In Madison, Indiana, there are several pet-friendly house rentals available, with around 17 options to choose from. Many of these properties offer a range of amenities designed for comfort and convenience, such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.
Are there any remote work holiday rentals in Madison?
In Madison, Indiana, there is a good selection of remote work holiday rentals, with around 53 available. Many of these properties cater specifically to remote workers, featuring amenities such as high-speed Wi-Fi, dedicated office spaces, desks with comfortable chairs, and sometimes even computer monitors for an efficient working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Madison holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Madison with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Madison?
In Madison, Indiana, holiday rentals commonly feature essential amenities that cater to travellers' needs. Most properties include a fully equipped kitchen, allowing guests to prepare their own meals, alongside a microwave and refrigerator for added convenience. Additionally, cookware, dishware, and utensils are typically provided, making it easy for visitors to enjoy home-cooked meals during their stay.
When is the best time to visit Madison for a holiday rental?
The best time to visit Madison, Indiana, for a holiday rental is during the vibrant summer months from May to July, with July being the most popular. This peak season attracts families and adventure enthusiasts eager to enjoy the warm weather, local festivals, and outdoor activities. Stroll along the picturesque riverfront, explore the charming historic district, or take part in the various community events that showcase the area's culture.

During this season, temperatures typically hover in the mid to high 20s Celsius, creating an inclusive setting for outdoor sightseeing and leisurely walks through the scenic parks. The city comes alive with activities, making it an ideal time for those who appreciate a lively and engaging holiday experience.

For travellers looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience where you can enjoy the local scenery and the peacefulness of the off-peak season. The stunning autumn colours in the surrounding landscapes provide a beautiful backdrop for leisurely drives and cosy explorations.
How early should I book a Madison holiday rental?
Book your Madison holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Madison?
In Madison, Indiana, visitors can enjoy a variety of attractions that showcase the town's rich history and scenic beauty. The historic downtown area is lined with charming shops and restaurants, with great sites such as the Madison Historic District, where beautifully preserved 19th-century buildings can be explored.

The Lanier Mansion State Historic Site offers guided tours of the grand residence, providing insights into the area's past. For those interested in outdoor activities, Clifty Falls State Park is nearby, featuring picturesque hiking trails, waterfalls, and opportunities for picnicking amidst nature.
Can I change or cancel my Madison home rental booking on Vrbo?
To find Madison holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Madison holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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