Holiday Rentals in Madison, CT

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Madison, CT holiday rentals
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156 Holiday rentals and Airbnb in Madison, CT

Best family friendly Madison, CT holiday rentals

Among the 156 accommodations in Madison, CT, here are the 1 best family friendly rentals

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.6 13 reviews

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger

apartment, Haddam
This waterfront property is located in Killingworth, Connecticut, just a short distance from Cockaponset State Forest and Sundial Herb Garden, offering easy access to nature and local attractions. The property has received excellent guest ratings, highlighting its comfortable and enjoyable stay.
This four-bedroom house spans 121 square metres and comfortably accommodates up to 10 guests. It features a fully equipped kitchen, a terrace, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.

Best Madison, CT holiday rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 2 best rentals with a pool

Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

apartment, Killingworth
This charming four-bedroom apartment in Killingworth is a 40-kilometre drive from Hammonasset Beach State Park and a 27-kilometre drive from the Lyman Orchards Golf Course and Farmers Market. It has received excellent user ratings and is perfect for families or groups looking for a comfortable and convenient base to explore the surrounding area.
This spacious apartment offers 189 square metres of living space, comfortably accommodating up to eight guests. You'll enjoy a private pool and patio, covered parking, a fully equipped kitchen, a fireplace, a fire pit and barbecue grill, and a washer and dryer.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
No reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

house, Killingworth
This Killingworth holiday home, situated approximately 21 kilometres from Wesleyan University and 24 kilometres from the Goodspeed Opera House, offers a peaceful retreat in Connecticut.
The 189-square-metre property boasts four bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, terrace, free Wi-Fi, and a fully equipped kitchen with dishwasher.

Frequently asked questions about holiday rentals in Madison, CT

  • What should a first-time visitor not miss in Madison, CT?

    You definitely shouldn't miss the scenic beauty of Hammonasset Beach State Park, a popular spot for swimming, sunbathing, and picnicking. The Madison Historical Society Museum is also worth a visit, showcasing the town's rich history and culture.
  • What are the best Airbnb and holiday rentals in Madison, CT?

  • Which neighborhood in Madison, CT should you consider for a vacation rental?

    The area around the Madison Green is a great option for a vacation rental, with its charming shops, restaurants, and proximity to the beach. It's also close to the historic town centre and offers a vibrant, lively atmosphere.
  • What are the most popular Airbnbs in Madison, CT?

  • What are the top family-friendly attractions in Madison, CT?

    The Children's Museum of Southeastern Connecticut in nearby New London is a great choice for families, offering interactive exhibits and educational activities. Hammonasset Beach State Park is also a popular destination, with its sandy beach, playground, and nature trails.
  • What are the best holiday rentals with a pool in Madison, CT?

  • When is the best time to book a vacation rental in Madison, CT?

    To avoid peak season crowds and secure the best deals, it's recommended to book your vacation rental in Madison during the shoulder seasons, from April to May or September to October, when the weather is still pleasant but the crowds are smaller.
  • What are the best rentals for families and kids in Madison, CT?

  • What events or festivals should visitors check out in and around Madison, CT?

    Madison's annual July 4th celebration is a highlight, with a parade, fireworks, and live music. The Guilford Fair, held in late August, is another popular event, featuring agricultural exhibits, live entertainment, and carnival rides.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

  • What are the best budget-friendly activities in Madison, CT?

    A stroll along the scenic Madison shoreline is a free and enjoyable activity. The Madison Green is another great option, offering a tranquil setting for a picnic or simply relaxing outdoors.
  • What are the best restaurants with local dishes in Madison, CT?

    The Lobster Landing Restaurant is a local favourite, serving fresh seafood dishes, including their renowned lobster rolls. The Madison Beach Hotel also offers a fantastic dining experience with its elegant setting and locally sourced ingredients.
  • What are the best walking or cycling routes in Madison, CT?

    The Shoreline Greenway Trail, a multi-use path, offers scenic walking and cycling routes along the Connecticut coastline. The Madison Green to Hammonasset Beach State Park route is a popular choice, offering a combination of urban and coastal scenery.
  • Are there pet-friendly attractions in Madison, CT?

    Hammonasset Beach State Park welcomes leashed dogs on designated areas of the beach. The Madison Green also allows dogs on leash, providing a pleasant spot for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy compared to hotels, often with kitchens and living areas. They also provide a more home-like atmosphere and can be more budget-friendly, especially for larger groups or families.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison is home to the Madison Beach & Yacht Club, offering a variety of water sports activities, including sailing, swimming, and kayaking. The town also has several public parks with sports fields and courts for basketball, tennis, and other activities.

Popular destinations

Best Madison, CT holiday rentals with a balcony

Welcoming Tiny Home! Downtown & Beachy️ - Madison, CT
10 24 reviews

Welcoming Tiny Home! Downtown & Beachy️

apartment, Guilford
Seagrass Bungalow is a charming mini-home located in the centre of Guilford, just a short walk from the town green, shops, restaurants, and Jacobs Beach. This highly rated property has received excellent reviews from previous guests.
The self-catering bungalow can accommodate up to two guests and is perfect for a romantic getaway. Enjoy the private deck, outdoor shower, fire pit, and large grassy yard, or relax in the spa and take advantage of the on-site parking.

Best Madison, CT holiday rentals with parking

New Coastal Cottage 2 Miles To Beach + Lake Access - Madison, CT
10 8 reviews

New Coastal Cottage 2 Miles To Beach + Lake Access

apartment, Clinton
This holiday let in Clinton is located 3.2 kilometres from Hammonassett Beach and a short walk to Boulder Lake Beach, with downtown Madison and Clinton also 3.2 kilometres away.
This two-bedroom bungalow accommodates up to six guests and features air conditioning, Wi-Fi, a microwave oven, a dishwasher, and a screened-in porch with an outdoor picnic table and fire pit.
Walk To Coast! Convenient Cottage In Dtwn Madison - Madison, CT
8.0 1 review

Walk To Coast! Convenient Cottage In Dtwn Madison

apartment, Madison
This apartment is located in downtown Madison, offering walkable access to East Wharf Beach Park and Seaview Beach, and is within 1 kilometre of the Shoreline Greenway Trail.
This 51 square meter, one-bedroom flat accommodates up to four guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and a washer/dryer, with step-free entry to the two-story studio cottage.
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.8 11 reviews

2 Mi To Dtwn: 2-acre Retreat W/ Large Yard!

apartment, Madison
This Madison seaside property is situated less than 2km from Hammonasset Beach State Park, the Allis-Bushnell House and Museum, and the Scranton Memorial Library, with RJ Julia Booksellers and Anna Mia's also nearby.
This 372 square metre house offers four bedrooms, three bathrooms, sleeps six guests, and boasts a fully equipped kitchen, terrace, garden, parking, and air conditioning.
Walk To Coast! Convenient Cottage In Dtwn Madison - Madison, CT
No reviews

Walk To Coast! Convenient Cottage In Dtwn Madison

studio, Madison
This downtown Madison flat offers a prime walk-to-coast position, located 2.2 kilometres from Hammonasset Beach State Park and 32 kilometres from Yale University.
This 51 square metre property features one bedroom, one bathroom, air conditioning, private parking, and complimentary WiFi, with a fully equipped kitchen and an in-unit washing machine.
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