Discover a selection of 23 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 $77 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.
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

Activities and attractions in Madison

Do you want to find things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Madison a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chamard Vineyards (1.7 mi / 2.8 km)
  • Chatfield Hollow State Park (4.9 mi / 8 km)
  • Essex Steam Train (9.6 mi / 15.5 km)
  • Connecticut Sportsplex (12.7 mi / 20.5 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Powder Ridge Mountain Park and Resort (16.6 mi / 26.7 km)

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

Transportation to and around Madison

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 16.5 mi (26.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away.

What are the top vacation rentals in or near Madison?

Whatever you're seeking in a vacation, you'll find a rental in or around Madison that fits you like a glove. These are some of our favorites:

  • "Beach Cottage Close To Silver Sands State Park" is a hit with guests. Around 25 miles from Madison, it has 2 bedrooms and plenty of handy amenities, including a stovetop and a nearby beach.
  • Alternatively, unpack your suitcase at "Family House Near Hammonasset Beach State Park". Located around 1 mile from the heart of Madison, it has 4 bedrooms and features a fenced yard and a playground.

For even more great options, use the search bar at the top of the page to find the perfect Madison vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Madison?

If you've been busier than an ant in a picnic basket, you deserve to escape for a couple of glorious days. Leave work early on Friday and live it up at one of these weekend getaways in or near Madison:

  • "Birdsong - Relaxation, Activities And Culture In Quaint Shoreline Town" is perfect for a couple of days of R&R. It comes with a host of amenities, such as a smart TV and towels, and is located about 2 miles to the northwest of Madison.
  • Or, toss a few clothes in an overnight bag and enjoy a mini break at "Madison, Ct - Coastal Modern Farmhouse W". This well-liked property is around 4 miles south of Madison and features a fridge and games.

Can I find studio apartments for rent in and around Madison?

Studio apartments are a simple yet stylish option, ideally suited for traveling sweethearts or solo stays. Spend your days getting acquainted with your surroundings and your nights chilling out in your comfy hideaway. These vacation rentals in or near Madison are sure to please:

  • After a big day of outdoor exploration, come home to the comforts of "Birdsong - Relaxation, Activities And Culture In Quaint Shoreline Town". A kitchen and beach sun loungers are among the handy amenities you'll find here.
  • Alternatively, use "Cozy Summer Cottage In Quiet Condo Community" as a base to check off the best attractions around you. This comfy home away from home comes with shopping, coffee and tea making facilities and more.

Can I find short term rentals in or near Madison?

Whether you're looking for a small apartment for you and a friend or a villa big enough for the whole family, there's no shortage of short-term rentals in and around Madison. These retreats make a comfortable base for a quick trip:

  • For a fantastic few nights away, it's hard to go past "Adorable Cottage Close To Beaches And Town". It's near the center of Madison, in addition to plenty of things to see and do.
  • Alternatively, spend a couple of relaxing nights at "Sundrenched 5 Bedroom Home With Private Dock Near Beaches". This comfy, centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Madison?

Whether spent in a cabin, a cottage or a condo, a romantic weekend getaway is an excellent way to add some fire to your relationship. Whisk your sweetheart away for a couple of days at one of these top escapes in or near Madison:

  • Sneak off on Friday afternoon for a couple of passion-filled evenings at "Beach Cottage Close To Silver Sands State Park". Around 25 miles from Madison, this property comes with plenty of nice touches, like a nearby bay and a nearby marina.
  • Alternatively, spend a few blissful days sipping wine and canoodling at "Family House Near Hammonasset Beach State Park", around 1 mile from Madison. A nearby bay and winery tours will help ramp up the romance.

What are the best large group vacation rentals in or near Madison?

Big groups mean gigantic fun. They also mean finding someplace that'll comfortably fit your whole gang. Check out our large group vacation rentals in or around Madison and get everyone together under the same roof:

  • A wide array of amenities including a kitchen and a swimming pool make "Waterfront Estate Home - Beach And Shared Pool" a favorite with groups. This retreat has 9 bedrooms and sleeps up to 20 guests. From the center of Madison, it's around 4 miles away to the south.
  • Nothing takes priority over spending time with the people you love, and "The Queen Of The Thimble Islands" makes it easy to do that. Located around 8 miles to the southwest of Madison, as many as 15 guests can stay in this vacation rental which has 8 bedrooms. A garden and a kitchen are among the numerous amenities you'll have at hand.

What are the best houses for rent with a pool in or near Madison?

Nothing says fun and frivolity like a pool does. Dig out your inflatable flamingo and browse these rental houses in or near Madison that come with this must-have amenity:

  • Pack your swim gear and make yourself comfortable at "Family House Near Hammonasset Beach State Park". There are also lots of other great amenities here, including a microwave oven and a dishwasher.
  • "Private Beachfront House In Madison Ct" is the sort of place you go to get away from it all and enjoy your surroundings, starting with its awesome pool. A kitchen and a TV are also on hand to make your visit nice and comfortable.

Curious what the weather is like in Madison? It has a humid subtropical climate, with average summertime temperatures ranging from 65 ºF to 80 ºF. If you're seeking a little more inspiration on places to stay in this exciting destination, use the search bar at the top of the page and adjust the filters to scroll through our entire range of Madison vacation rentals.

What are the best large family vacation rentals in or near Madison?

Whether your perfect escape is high in the hills or by the beach, you'll have so much more fun if you share it with those closest to you. Choose one of these large family vacation rentals in or near Madison and bring the whole crew:

  • Get everyone under the same roof at "Family House Near Hammonasset Beach State Park", which has 4 bedrooms sleeping up to 10 guests. This escape is around 1 mile to the east of Madison and features amenities such as cable/satellite TV services and a fenced pool.
  • Another great option is "Steps To Beach; Walk To Town". This large rental is 4 miles southeast of Madison and comes with a TV, a kitchen island and more. With 4 bedrooms accommodating up to 8 people, you won't have to leave anyone off your invitation list.

When you want to explore your surroundings, there are plenty of family-friendly attractions nearby to keep everyone happy. Lighthouse Point Carousel, Connecticut Children's Museum and Shepaug Eagle Observation Area should be top of your agenda.

Are there vacation rentals with fire pits in or near Madison?

Crackers, chocolate, marshmallows and a campfire are the four ingredients you need to make a tasty snack and epic vacation memories. If you love the sound of huddling around a fire pit nibbling on s'mores, look into these retreats in or around Madison:

  • Laugh, sing and reconnect with friends and family around the fire at "Family House Near Hammonasset Beach State Park". This escape comes with plenty of other top amenities, such as a swimming pool and a fireplace.
  • Stoke the embers and then savor the relaxed atmosphere at "Madison, Ct - Coastal Modern Farmhouse W". This sought-after pad also comes with a kitchen and a firepit.