Madison holiday rentals

We found 136 holiday rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Scroll through and select from holiday rentals in Madison to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Madison getaway

Learn about the unique charm of Madison with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Madison

Are you looking for attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Madison a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bay Country Shop (9.5 mi / 15.2 km)
  • Phillips Wharf Environmental Center (15.6 mi / 25.1 km)
  • Perigeaux Vineyards and Winery (16.6 mi / 26.8 km)
  • Layton's Chance Vineyard and Winery (17 mi / 27.4 km)

Exploring the natural features in Madison

Whether you're an outdoor enthusiast or just want to take in the scenery, Madison is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Harriet Tubman Underground Railroad National Historical Park (6 mi / 9.7 km)
  • Blackwater National Wildlife Refuge (8 mi / 13 km)
  • Calvert Cliffs State Park (14 mi / 22.5 km)
  • Breezy Point Beach (17.6 mi / 28.4 km)
  • Long Wharf Park (9.3 mi / 15 km)
  • Bill Burton Fishing Pier State Park (11.2 mi / 18.1 km)

Transport to and around Madison

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 22.7 mi (36.5 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Madison?

Based on our research, houses are considered the most popular type of property in Madison. But of course, everyone's idea of an epic trip isn't going to be the same. Vrbo has holiday homes of all sizes and shapes, and we'll help you find the best fit for your needs.

How much does it cost to rent a holiday home in Madison?

The average price for a holiday home in Madison can vary based on factors including length of stay, property type and season. Whether you're looking for a sprawling villa with lots of bedrooms or a quaint cottage for just you and your sweetheart, just add your dates of travel to discover stays with amazing value.

How much does it cost to rent a beach house in Madison?

When you travel and the style and size of the property will help determine the cost of your beachside stay. Enter your Madison travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to choose the amenities and features you want in your holiday home.

Are there pet-friendly holiday homes in Madison?

You're in luck. There are. You can pick from two holiday homes that allow pets in Madison on Vrbo. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly holiday homes to find a property where Rover can get in on the fun.

What are popular home amenities in Madison?

The most popular home amenities people search for in Madison are a fireplace, a firepit and a garden. Whether you're going on holiday with family, your besties or even pets, Vrbo holiday properties come with the best amenities for beginning new traditions with your loved ones.

Are there holiday homes in Madison that welcome kids?

Gather your whole crew for a fun-filled adventure in Madison at one of our two family-friendly holiday homes. Many of these stays feature amenities that are ideal for getaways with children, such as full kitchens, multiple bedrooms and private pools. Simply click on the "Properties good for families" filter and choose your favourite option.

What are the top attractions for families in Madison?

Keeping the kids entertained during your holiday in Madison is easy with these awesome family-friendly attractions:

  • Richardson Maritime Museum
  • Choptank River Lighthouse
  • Long Wharf Park

How can I find holiday homes with air conditioning in Madison?

Pick from two Vrbo holiday homes with air conditioning in Madison giving you that gentle, cool breeze and extra level of comfort. Enter your chosen travel dates and then use our handy filter tool to locate stays with air conditioning.

How old do you have to be to rent a holiday home in Madison?

You should check with the Madison holiday property you want on Vrbo as the age limit varies. However, it's typically 16, 18 or 21.

How long can I rent a holiday home in Madison for?

It all depends on the Madison property. To browse available options offering extended stays, simply enter your dates and guest number into Vrbo. Look forward to having the property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and a backyard to play in. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

More Holiday Rentals ideas