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

Charm + Location. Walk To Beach, Town, & Harbor. - Madison, CT
9.9 296 reviews
Madison, CT
24/08 – 27/08
281 €/nighttotal: 843 € (3 )

Charm + Location. Walk To Beach, Town, & Harbor.

1 2
apartment , Guilford
This charming cottage is ideally situated in Guilford, within easy walking distance of the town's main attractions, including the green, the harbour, and the beach. It boasts excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage offers two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy its well-equipped kitchen, spacious living areas, screened porch, large side yard, and bike rentals, perfect for exploring the area.
Private Beach, 3 Bedroom House Right On The Water - Madison, CT
10 7 reviews
Madison, CT
12/07 – 16/08
717 €/nighttotal: 25095 € (35 )

Private Beach, 3 Bedroom House Right On The Water

1 3
house , Clinton
This three-bedroom apartment is located on Kelsey Point in Clinton, just a short walk or bike ride from Hammock Beach, offering a tranquil escape with stunning ocean views. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment comfortably sleeps eight guests and features a spacious kitchen and two living areas, perfect for family gatherings. Guests can enjoy access to a private beach, paddle boards, beach chairs, a fire pit, and a screened porch with a hammock and outdoor shower, providing ample opportunities for relaxation and outdoor activities.
Waterfront Goodspeed Airport 2-bedroom House With Ac, Wifi - Madison, CT
9.6 15 reviews
Madison, CT
27/06 – 04/07
416 €/nighttotal: 2912 € (7 )

Waterfront Goodspeed Airport 2-bedroom House With Ac, Wifi

2 4
apartment , East Haddam
This East Haddam waterfront property is situated directly on the Connecticut River, adjacent to Goodspeed Airport and within walking distance of the Goodspeed Opera House.
The two-bedroom, two-bathroom house sleeps six guests and offers amenities including kayaks, Starlink Wi-Fi, and a garden, plus proximity to Machimoodus State Park and the Essex Steam Train.
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.

Best Madison, CT holiday rentals with a pool

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

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.
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.
Resort Style Getaway W/pool, Spa, Game Room & More - Madison, CT
9.9 119 reviews
Madison, CT
11/07 – 18/07
1357 €/nighttotal: 9499 € (7 )

Resort Style Getaway W/pool, Spa, Game Room & More

5 4
apartment , East Haddam
This spacious home is located just 1.6 kilometres from the charming East Haddam Center, offering easy access to the Connecticut River, Gillette Castle, and the town beach. It has received excellent ratings for user experience, location, and cleanliness.
The property spans 418 square metres and comfortably accommodates up to 14 guests. Amenities include a private resort-style patio with a pool, hot tub, fireplace, fire pit, bar and grill, 65" TV, outdoor bathroom, and shower, a game room with a pool table, ping pong table, arcade basketball, poker table, and foosball, and a kitchen with a fridge, freezer, microwave oven, and dishwasher.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
Madison, CT
24/06 – 28/06
1311 €/nighttotal: 5244 € (4 )

Stunning Historic Waterfront Mansion With Pool

5 8
apartment , Clinton
This historic 5-bedroom former Clinton Country Club Clubhouse offers direct waterfront views of Clinton Harbour and Meigs Point, situated less than 1 kilometre from Clinton's shops and restaurants.
This luxury flat accommodates up to 10 guests with a chef's kitchen featuring Sub-Zero appliances, a Gunite swimming pool, multiple decks, and private nanny quarters, all equipped with air conditioning, Wi-Fi, and parking.

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

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
24/08 – 27/08
1452 €/nighttotal: 4356 € (3 )

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.
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.
2 Mins/350 Ft Walk To West Beach 4-br Cottage In Westbrook, Ct With Large Yard - Madison, CT
9.4 10 reviews
Madison, CT
27/06 – 04/07
324 €/nighttotal: 2268 € (7 )

2 Mins/350 Ft Walk To West Beach 4-br Cottage In Westbrook, Ct With Large Yard

4 4
cottage , Westbrook
This charming cottage in Westbrook Centre is just a stone's throw from West Beach and a short walk from the town centre, offering a peaceful retreat in a classic New England setting. It has consistently received excellent user ratings, making it a popular choice for travellers.
This spacious four-bedroom property, spanning 93 square metres, comfortably sleeps seven guests. The cottage offers a range of amenities, including a well-equipped kitchen, a private garden, a terrace, and a hot/cold outdoor shower, perfect for enjoying the beautiful weather and exploring the surrounding attractions.
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included - Madison, CT
Madison, CT
02/08 – 07/08
329 €/nighttotal: 1645 € (5 )

Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included

1 4
apartment , Westbrook
This Westbrook flat is centrally located in Westbrook Centre, a four-minute drive from West Beach and less than 1 kilometre from the Westbrook Outlets.
This one-bedroom, 50-square-metre flat accommodates up to four guests and features a Level 2 EV charger, off-street parking, air conditioning, a kitchen with a fridge, microwave, and dishwasher, and a spacious living area with a 55-inch television.

Best Madison, CT holiday rentals with parking

The Connecticut Cottage Historic Modern Charm - Madison, CT
Madison, CT
02/08 – 07/08
509 €/nighttotal: 2545 € (5 )

The Connecticut Cottage Historic Modern Charm

2 4
cottage , Clinton
This 1790s stone holiday home in Clinton offers a prime shoreline position, located 5 minutes' drive from Clinton Outlets and Town Beach, and 10-15 minutes' drive from Madison Beaches and Old Saybrook Historic Downtown.
This two-bedroom, two-bathroom holiday home accommodates up to four guests and features air conditioning, Wi-Fi, a garden, and parking, with nearby attractions including the Allis-Bushnell House and Museum and the Hyland House Museum.
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt - Madison, CT
8.8 23 reviews
Madison, CT
02/08 – 07/08
251 €/nighttotal: 1255 € (5 )

Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt

2 4
apartment , East Haddam
This East Haddam apartment is ideally located a two-minute walk from the Goodspeed Opera House, 27 kilometres from Wesleyan University, and 45 kilometres from Eastern Connecticut State University.
This two-bedroom, one-bathroom flat offers 84 square metres of space, sleeping up to nine guests and boasting a fully equipped kitchen, air conditioning, free on-site parking, and a private entrance.
“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.
Tranquil Lakefront Home @ Hidden Lake - Madison, CT
9.7 48 reviews
Madison, CT
24/06 – 28/06
480 €/nighttotal: 1920 € (4 )

Tranquil Lakefront Home @ Hidden Lake

1 8
apartment , Haddam
This lakefront house in Haddam is a short distance from the town centre, offering easy access to historic landmarks and local amenities. It has received excellent ratings for its cleanliness, location, and overall experience.
This spacious home can accommodate up to eight guests in its four bedrooms and one bathroom. Guests can enjoy a range of amenities, including a fire pit, a large garden, a dock, and a dedicated workspace, ensuring a comfortable and enjoyable stay.
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