0 Bedrooms for 1 Guest
Price $10 - $1000+

179 Madison Vacation Rentals & Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Madison vacation rentals from 5 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $43 to $1000 a night. 

    Information about Madison

    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

    Looking for the perfect vacation rental for your Madison getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Madison offers 179 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 93 properties with high-speed internet, 4 full with jacuzzi and pool, and NaN homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

    For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $7631 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Madison has 179 gorgeous homes with 34 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

    Search properties from 5 rental sites in Madison where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 101 HomeAway rentals, 55 Booking.com short term rentals and 14 TripAdvisor vacation rentals.