We found 259 vacation rentals — enter your dates for availability
Discover a selection of 259 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 $130 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.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find the best place to stay — Madison
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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.
Activities
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.
Weather
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 259 vacation rentals around Madison. From 233 house rentals to 71 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:
- Hammonasset Beach State Park: 781 vacation rentals
- Allis-Bushnell House and Museum: 686 vacation rentals
- Meigs Point Nature Center: 800 vacation rentals
- North Madison Shopping Center: 390 vacation rentals
- Deacon John Grave House: 671 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 233 Houses in Madison. Our other popular types of vacation rentals in Madison include:
- Cottages: 71 rentals available
- Cabins: 71 rentals available
- Bungalows: 71 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 23 vacation rentals with pool available in Madison. Please use our search bar to access the selection of vacation rentals available.