Holiday Rentals in Madison, CT

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

Best family friendly Madison, CT holiday rentals

Among the 105 accommodations in Madison, CT, here are the 4 best family friendly rentals

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.8 11 reviews
Madison, CT
24/08 – 27/08
595 €/nighttotal: 1785 € (3 )

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

4 2
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.
Guilford Shoreline Private Home - Madison, CT
Madison, CT
07/09 – 30/09
568 €/nighttotal: 13064 € (23 )

Guilford Shoreline Private Home

1 2
apartment , Guilford
This apartment is located in the centre of Guilford, just a short walk from 20 restaurants, the waterfront, and the Norman Rockwell green, offering easy access to the town's attractions. The charming, historic town atmosphere adds to the appeal of this property.
This comfortable flat can accommodate up to five guests and has two bathrooms. It comes with a fully equipped kitchen, air conditioning, a private garden, a fitness centre, and parking. The apartment is also close to the beach, a farmer's market, and live music venues.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews
Madison, CT
07/09 – 30/09
533 €/nighttotal: 12259 € (23 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
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.
Madison Cozy Studio With Private Entrance - Madison, CT
9.8 580 reviews
Madison, CT
07/09 – 30/09
132 €/nighttotal: 3036 € (23 )

Madison Cozy Studio With Private Entrance

1 2
studio , Madison
This self-contained apartment is situated in a peaceful residential area in Madison, Connecticut, just 5 kilometres from the beach and the Shoreline East train station. The accommodation has consistently received excellent ratings for its cleanliness, location, and overall experience.
The studio has a separate entrance and bathroom, offering privacy for up to 4 guests. Amenities include a small fridge, microwave, coffee maker, Wi-Fi, air conditioning, and a private outdoor space with a fire pit and patio furniture.

Best Madison, CT holiday rentals with a pool

Among the 105 accommodations in Madison, CT, here are the 4 best rentals with a pool

Stay Aboard Mini-expedition Trawler Mary South - Madison, CT
Madison, CT
12/07 – 16/08
127 €/nighttotal: 4445 € (35 )

Stay Aboard Mini-expedition Trawler Mary South

2 3
boat , Clinton
The Mary South, a unique mini-expedition ship, is docked at Clinton Yacht Haven, offering convenient access just 1.6 kilometres from Hammonnasset Beach and State Park.
This vessel provides accommodation for four guests, featuring two bedrooms and two bathrooms, with amenities including air conditioning, internet, a kitchen, and access to the yacht haven's swimming pool and clubhouse.
Roof Top Pool, Ocean Views, Private Beach! - Madison, CT
Madison, CT
12/07 – 16/08
681 €/nighttotal: 23835 € (35 )

Roof Top Pool, Ocean Views, Private Beach!

1 3
apartment , Clinton
This Clinton flat, situated at the highest point of the shoreline, offers direct, private beach access and unparalleled panoramic ocean views, with sunrises and sunsets over the water.
Boasting old-world charm and rustic luxury, this Mediterranean-inspired dwelling accommodates up to five guests across two bathrooms, featuring a private plunge pool, outdoor shower, on-site kayaking, and potential discounts on Blue Heron Cruises.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
Madison, CT
07/09 – 30/09
547 €/nighttotal: 12581 € (23 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
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.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
07/09 – 30/09
1168 €/nighttotal: 26864 € (23 )

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.

4 2
houseboat , Clinton
This houseboat is situated in Clinton, Connecticut, offering convenient access to RJ Julia Booksellers, located just 300 meters away, and is within easy reach of Clinton Crossing Premium Outlets and Clinton Plaza Shopping Center.
This four-bedroom, four-bathroom vessel accommodates up to eight guests, featuring a king bed, queen bed, and two twin beds, complete with air conditioning and internet, and boasts a flybridge bar and aft deck dining area for enjoying panoramic views.

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.

Destinations nearby

Best Madison, CT holiday rentals with a balcony

Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 4 reviews
Madison, CT
24/08 – 27/08
480 €/nighttotal: 1440 € (3 )

Newly Renovated Carriage House Near Town & Beaches

2 2
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.
The Millhouse Downtown Chester - Madison, CT
10 116 reviews
Madison, CT
02/08 – 07/08
469 €/nighttotal: 2345 € (5 )

The Millhouse Downtown Chester

2 4
apartment , Chester
The Millhouse Downtown Chester is situated in the centre of Chester, just 8km from the Goodspeed Opera House and 27km from Wesleyan University. This apartment has received excellent ratings for its location, cleanliness and overall experience.
The accommodation is a 2-bedroom, 2-bathroom apartment spanning 102 square metres. The property offers a range of amenities including a fully equipped kitchen, private parking, a terrace with river views, an outdoor fireplace, and access to streaming services.
Grace Island.   Private Island!  Vacations, Getaways, Weddings & Special Events. - Madison, CT
Madison, CT
12/07 – 16/08
6184 €/nighttotal: 216440 € (35 )

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

11 3
apartment , Branford
Grace Island, a short distance off the coast of Branford, Connecticut, offers a secluded escape just a stone's throw from Farm River State Park and West Rock Ridge State Park. This historic island, built in 1850, provides a unique blend of history and modern comfort.
The 604 square metre property boasts 11 bedrooms, 6 bathrooms, and can accommodate up to 22 guests. Grace Island offers a range of amenities including a fully equipped kitchen, a spacious garden, a tennis court, and a terrace, perfect for enjoying the island's natural beauty.
Quarry House: Mid-century Modern - Madison, CT
9.0 2 reviews
Madison, CT
02/08 – 07/08
1079 €/nighttotal: 5395 € (5 )

Quarry House: Mid-century Modern

4 4
apartment , Haddam
This Haddam, Connecticut property, a mid-century modern house situated on a hill overlooking a river, is near the Goodspeed Opera House and other attractions.
The 202-square-metre (approximately 2178 square feet) dwelling boasts four bedrooms, three bathrooms, and can accommodate eight guests, featuring a kitchen with fridge, microwave, and dishwasher, plus air conditioning, a terrace, garden, and parking.

Best Madison, CT holiday rentals with parking

Waterfront Apartment-guilford Ct-***new Listing - Madison, CT
9.9 79 reviews
Madison, CT
24/08 – 27/08
308 €/nighttotal: 924 € (3 )

Waterfront Apartment-guilford Ct-***new Listing

1 2
studio , Guilford
This Guilford waterfront studio apartment is situated a short walk from a public beach, five minutes from Guilford's town docks and marina, and fifteen minutes from the town green.
The self-catering apartment, sleeping two, features a queen-sized bed, a small but well-equipped kitchen with fridge and freezer, air conditioning, a private bathroom, and a private garden offering stunning Long Island Sound views and opportunities for birdwatching.
Relax In A Cabin By The Beach (Cottage No.1) - Madison, CT
9.5 29 reviews
Madison, CT
24/08 – 27/08
202 €/nighttotal: 606 € (3 )

Relax In A Cabin By The Beach (Cottage No.1)

1 2
apartment , Madison
This Madison cottage is situated near Madison's beach and greenway trail, a short drive (approximately 1.6 to 3.2 km depending on the specific location within Madison) from the town centre.
The self-catering property sleeps two adults and a child, boasting a queen-size bed, a mini-fridge, coffee maker, microwave, toaster, and air conditioning; a pack 'n play is available for infants.
Shoreline Oasis - Madison, CT
9.4 8 reviews
Madison, CT
07/09 – 30/09
177 €/nighttotal: 4071 € (23 )

Shoreline Oasis

1 2
apartment , Clinton
This Clinton city-centre apartment offers easy access to the waterfront, train station, and Lobster Landing, with Hammonassett State Park and Chamard Vineyards within a short 8km drive.
The 51-square-metre self-contained flat comprises one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, Netflix/Hulu access, a terrace, and private parking.
“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach - Madison, CT
9.9 82 reviews
Madison, CT
12/07 – 16/08
374 €/nighttotal: 13090 € (35 )

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

4 3
apartment , Clinton
This apartment is located in Clinton, Connecticut, just 3.2 kilometres from the beach and within easy reach of shops, restaurants, and shopping outlets. It has received excellent ratings for its cleanliness, location and user experience.
The apartment offers four bedrooms, sleeping up to six guests, and is perfect for families or groups of friends. It features a well-equipped kitchen, a spacious four-season porch, a large garden and private parking.
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