Compare Vacation Rentals & Airbnb in Madison, CT

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Madison, CT vacation rentals
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156 Rentals and Airbnb in Madison, CT

Best family friendly Madison, CT vacation rentals

Among the 156 accommodations in Madison, CT, here are the 2 best family friendly rentals

Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 32 reviews

Daniel Boone Meets Mid Century Modern Retreat

cabin, Killingworth
This expansive five-bedroom lodge in Killingworth, Connecticut, offers 232 square meters of living space and is conveniently located near Chatfield Hollow State Park, Chamard Vineyards, and a short drive from Clinton Crossing Premium Outlets.
Guests can enjoy a mid-century modern sanctuary with a fully equipped kitchen, an on-site gym, and outdoor patios with a grill, perfect for exploring the surrounding 24 acres or visiting nearby attractions such as the Ivoryton Playhouse and Mystic Seaport, with year-round outdoor activities like hiking and apple picking readily available.
Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 6 reviews

Newly Renovated Carriage House Near Town & Beaches

apartment, Madison
This newly renovated carriage house is located in Madison, just 11 kilometres from Hammonasset Beach and within easy reach of Thimble Islands, City Hall and Yale University. The apartment has received excellent ratings for location, cleanliness and user experience.
The property offers two bedrooms and one bathroom, providing comfortable accommodation for up to four guests across 58 square metres. The apartment includes a private terrace, a garden, free Wi-Fi, a fully equipped kitchen, air conditioning and private parking.

Best Madison, CT vacation rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 1 best rentals with a pool

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 vacation rentals in Madison, CT

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

    For a first-time visit, you should definitely check out the Madison Beach & the charming shops and restaurants on Boston Post Road. The historic town green is also a must-see, with the iconic Madison Town Hall.
  • What are the best Airbnb and vacation 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 choice for a vacation rental. It's close to the beach, shops, and restaurants. Alternatively, the more residential neighbourhoods of North Madison or West Madison could be good choices if you prefer a quieter setting.
  • What are the most popular Airbnbs in Madison, CT?

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

    The Hammonasset Beach State Park is a fantastic spot for families, with a large beach, a playground, and a nature centre. The Madison Surf Club is a great place to learn to surf or just enjoy the beach.
  • What are the best vacation rentals with a pool in Madison, CT?

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

    The summer months are the busiest time in Madison, so booking your vacation rental in advance is essential. You can also find some good deals in the shoulder seasons, like spring and autumn, 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?

    The Madison Beach & Food Festival in July is a popular event, and the annual Madison Arts Festival in September is a great way to experience the local art scene. The nearby town of Guilford also hosts a number of events throughout the year, including the Guilford Fair in August.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

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

    The Madison Green is a great place to relax and enjoy the outdoors, and it's completely free. The Madison Historical Society offers free tours of the historic town hall, and the nearby Hammonasset Beach State Park has free access to the beach and trails.
  • What are the best restaurants with local dishes in Madison, CT?

    For a taste of local seafood, try The Lobster Shack on the waterfront. The Madison Beach Cafe is another popular spot for fresh seafood, and The Griswold Inn is a historic tavern that serves classic New England cuisine.
  • What are the best walking or cycling routes in Madison, CT?

    The scenic coastal path along the shoreline is a great option for walking or cycling. The Hammonasset Beach State Park also has a network of trails for hiking and biking.
  • Are there pet-friendly attractions in Madison, CT?

    Hammonasset Beach State Park is dog-friendly, and the nearby East River Park in Guilford also allows dogs on leash. Many restaurants and shops in Madison are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy than hotels, and they often have kitchen facilities, making it easier to cook your own meals. They can also be a more budget-friendly option, especially for larger families or groups.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison is known for its sailing and boating, with the Madison Yacht Club and the Madison Surf Club offering a range of activities. The town also has several parks and recreational facilities, including the Hammonasset Beach State Park, which has a variety of trails for hiking and biking.

Popular destinations

Best Madison, CT vacation rentals with a balcony

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.
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.
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.
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.

Best Madison, CT vacation 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.
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.
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly! - Madison, CT
10 1 review

Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!

apartment, Clinton
This lakefront holiday home in Clinton is located in a wooded, natural setting, a 1-minute walk from beach-style lake access and a short distance from the Adam Stanton House and General Store Museum and Scranton Memorial Library.
This four-bedroom, four-bathroom flat accommodates up to eleven guests, featuring a two-level layout with a private deck, hot tub, and fireplace, with amenities including a fridge, microwave, and air conditioning.
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