Madison vacation rentals

We found 136 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Madison to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include WiFi and a hot tub. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Choose a vacation rental for your Madison getaway

Learn about the unique charm of Madison with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. With a vacation 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 hoping to discover attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Madison a fun spot to vacation. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 spend some time taking in the scenery, Madison is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Great Marsh Park (9.3 mi / 15 km)

Transportation to and around Madison

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

Frequently asked questions

What is the most popular type of vacation rental 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 vacation rentals 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 vacation rental in Madison?

The average price for a vacation 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 vacation home.

Are there pet-friendly vacation rentals in Madison?

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

What are popular rental amenities in Madison?

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

Are there vacation rentals in Madison that welcome kids?

Gather your whole crew for a fun-filled adventure in Madison at one of our two family-friendly vacation 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 favorite option.

What are the top attractions for families in Madison?

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

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

How can I find vacation rentals with air conditioning in Madison?

Pick from two Vrbo vacation 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 vacation rental in Madison?

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

How long can I rent a vacation rental 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.