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Compare Madison holiday rentals from 6 rental sites including HomeAway, Expedia, and more, from $70 a night.

Madison Information

About Madison

Madison is located on the southeastern coast of Connecticut, and is the perfect place to spend a relaxing vacation alone, or with a loved one. Whether you find yourself spending your days on the beach, or if you want to explore the many parks and restaurants near the New Haven area; you are guaranteed a good time out on Connecticut’s Long Island Sound shoreline.

Things to do in Madison

Madison is best known for not being known, but there are many fun things to do in the quiet city. Take a walk down the Sculpture Mile to explore cool art pieces, or to just read a book on a bench in the park-like area. If you come in-between May and October, check out the Antique Shows that tour through the area, and maybe pick up a few things for your house, or gifts for friends. In June, the Strawberry Festival is the place to see art and taste food from vendors coming from surrounding areas. Shoppers should be sure to plan a trip during the annual Madison sidewalk sale, an event that is hosted by many of the merchants in the city. Interested in staying close to the coast? Spend your days at East Wharf, West Wharf, or The Surf Club—the three beaches in the city.

Madison Day Trips

There are some really fun day trips you can take from Madison. Just 30 minutes west is New Haven, a city filled with a fun history and a peaceful ambience. A two-hour car ride will land you in the heart of NYC, where you can explore the Big Apple for a day (or maybe two!) For a little more of a historical trip, drive about two hours to Plymouth, and explore the land of the first settlers from England. Interested in a beach day out of the state? Head out to Long Beach, New York, and sip on some drinks by the water. For more city travel, you can drive upwards to Boston and spend time checking out Harvard, or going to a Red Sox game. For a nature adventure, you can take a little bit longer of a journey to Vermont and experience the Green Mountain National Forest.

Madison Accommodations

Whether you choose to spend your vacation by the beach or more towards land, we make it super easy for you to find the best place to stay. For those looking to stay close to the coast, we offer tons of beachfront homes at all three of the beaches in the Madison area, all at an affordable price. Looking to take a drive north? We have houses available in Chester, a city closer to the middle of Connecticut. For a day trip to New Haven, we recommend staying in one of the hotels we offer near North Branford, a city 20 minutes away from the New Haven area. For a little bit higher of a price, we have houses available near Old Saybrook, a city that lies right on the ocean, and offers great views no matter where you are. Regardless of where you decide to stay, you can compare rentals by price, reviews, ratings, and more on Tripping. Book your Madison vacation rental today!

Transportation in Madison

There are quite a few ways to get around Madison. The Shore Line East train station runs every day with service to a variety of cities in Connecticut, including Madison, Old Saybrook, New London, and Branford. There is also a both Connecticut Transit and Estuary Transit District bus lines running throughout Madison. If water travel is your thing, the Cross Sound Ferry runs between New London and Long Island, New York. Looking to rent a car? There is an Enterprise Car Rental service located on Boston Post Road.

Vacation Rentals in Madison

Save hundreds with a vacation home rental from and forget the hotel room. For the ultimate getaway, Madison offers 38 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Madison start at an average price of $320 a night with long-term rentals averaging $25 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 31 of Madison’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 3 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 32 vacation home rentals.

Traveling with your dog or cat? Choose from 12 pet-friendly rentals in Madison that allow you to bring your extended family’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 6 vacation rental sites in Madison where the top providers in that area are HomeAway, Expedia, and There are 29 HomeAway rentals, 4 Expedia short term rentals and 2 vacation rentals.