Discover a selection of 281 vacation rentals in Madison, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $110 per night, and houses and cottages are popular options for a stay in Madison. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Madison
Destination guide

Discover New England's marvelous Madison

Nestled against the shoreline of Connecticut's Long Island Sound, and just a 30-minute drive from New Haven, Madison offers a postcard-perfect example of New England picturesque. From days spent shopping at the independent stores and eateries in the town's charming downtown to relaxing along the unspoiled coastline at Hammonasset Beach State Park, ample activities and attractions allow travelers to explore at their own pace. If you're planning to stay a while, Madison vacation rentals are the perfect way to stay close to the action, offering a relaxed base for your getaway, whether traveling with family, friends or both.

Things to do

Enjoy family adventures near Madison

Just a short drive from Madison vacation rentals, you'll find an array of attractions to keep the whole family entertained. Near the banks of the Connecticut River, the Essex Steam Train & Riverboat offers a variety of tours, including a 2.5-hour railroad excursion into the state's unspoiled river valley and a cruise to the spot where thousands of swallows swarm over the lower Connecticut River. A drive in the other direction leads to thrilling aerial escapades at the Adventure Park at the Discovery Museum, although those traveling without kids may prefer to check out some of the local wineries instead.


Find your perfect spot in Madison

Indoors or outside, Madison offers a quintessential New England experience. The town's quaint downtown features independent dining spots and boutique stores selling handcrafted bird boxes, not to mention an old-fashioned movie theater and a world-famous bookseller. Travelers keen to soak up more of the same can explore nearby New Haven, while those who prefer natural surroundings can find their perfect spot on the sand along the 2 miles of beachfront at Hammonasset Beach State Park. Over the summer, free events such as S'mores on the Shore movie nights and Wednesday-night concerts are a lovely way to end the day.


Seasonal appeal in Madison

Madison weather is fairly typical of New England. Daytime temperatures over the summer months of July and August can soar toward 90 degrees, although breezes floating in from Long Island Sound can prevent the stuffy air of further inland. Despite the appeal of spending sun-drenched summers in Madison vacation rentals, there's little debate that the best time to visit anywhere in New England is during fall. Brilliant colors start to turn the foliage into a dazzling display of red, orange and yellow - and the daytime temperatures are still plenty warm enough to get outside and enjoy the show.

Natural features

Natural wonders near Madison

The appeal of the unspoiled sandy beach at Hammonasset Beach State Park can't be understated but travelers willing to travel a little further afield will find numerous natural delights on the menu. The East River Wildlife Area, located at the edge of Madison's western border is home to all manner of creatures, including American oystercatchers and majestic great blue herons, making it the perfect spot for wildlife watching and photography. To the northeast of the town, the 16,000-acre Cockaponset State Forest offers hiking, horseback riding and mountain biking for much of the year, and cross-country skiing and snowmobiling in winter.

How to get there

Traveling to and around Madison

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 14.5 mi (23.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Oxford, CT (OXC-Waterbury - Oxford), which is 28.7 mi (46.2 km) away.

How many vacation rentals are available around Madison, CT?

Our 2021 property listings offer a large selection of 281 vacation rentals around Madison. From 249 house rentals to 74 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Madison?

Vrbo offers a large selection of vacation rentals near lovely places in Madison. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Allis-Bushnell House and Museum: 746 vacation rentals
  • North Madison Shopping Center: 447 vacation rentals
  • Deacon John Grave House: 727 vacation rentals
  • Scranton Memorial Library: 744 vacation rentals
  • RJ Julia Booksellers: 738 vacation rentals

But there are many other points of interest around Madison listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Madison?

Yes, of course. Vrbo has 249 Houses in Madison. Our other popular types of vacation rentals in Madison include:

  • Cottages: 74 rentals available
  • Cabins: 74 rentals available
  • Bungalows: 74 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Madison?

Yes, you can select your preferred vacation rental with pool among our 28 vacation rentals with pool available in Madison. Please use our search bar to access the selection of vacation rentals available.