Vacation 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

Edwin Leete House - Madison, CT
10 41 reviews
Madison, CT
11/12 – 12/12
A$1556/nightfor 1 night

Edwin Leete House

2 6
apartment , Guilford
The Carriage House is situated in Guilford's historic district, just a block from the Guilford Green and a short walk to the beach and marina. This charming property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom house can comfortably accommodate up to seven guests. The Carriage House offers a fully equipped kitchen, a private garden, parking, and air conditioning, ensuring a comfortable and enjoyable stay.
Private Beach, 3 Bedroom House Right On The Water - Madison, CT
10 7 reviews
Madison, CT
12/07 – 16/08
A$1180/nighttotal: A$41300 (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.
Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 5 reviews
Madison, CT
22/11 – 29/11
A$717/nighttotal: A$5019 (7 )

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.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews
Madison, CT
22/11 – 29/11
A$882/nighttotal: A$6174 (7 )

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.

Best Madison, CT holiday rentals with a pool

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

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
27/06 – 04/07
A$2196/nighttotal: A$15372 (7 )

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

4 4
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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 68 reviews
Madison, CT
22/11 – 29/11
A$1137/nighttotal: A$7959 (7 )

New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026

4 2
apartment , Madison
This waterfront holiday home in Madison, Connecticut enjoys a prime location with stunning views of the Long Island Sound and Neck River, just a short distance from Faulkner's Island. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The spacious cottage features an open-plan design with multiple bedrooms, accommodating up to eight guests. The property boasts a fully equipped kitchen, a large deck, a private beach, and access to a range of water activities, making it ideal for families and groups seeking a memorable holiday experience.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 10 reviews
Madison, CT
22/11 – 29/11
A$775/nighttotal: A$5425 (7 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
apartment , Killingworth
This holiday home is located in Killingworth, Connecticut, just a short drive from beaches, hiking trails, and lakes. It boasts excellent user, location, and cleanliness ratings.
This spacious property can accommodate up to 8 guests across 4 bedrooms and 2 bathrooms. Guests can enjoy a private pool, deck with a gas grill, fire pit, a walking trail, and a babbling brook, perfect for relaxing and enjoying the Connecticut weather.
Roof Top Pool, Ocean Views, Private Beach! - Madison, CT
Madison, CT
12/07 – 16/08
A$1121/nighttotal: A$39235 (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.

Frequently asked questions about holiday rentals in Madison, CT

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

    The Madison Beach is a must-visit for families, with its shallow waters and plenty of space for kids to play. The Hammonasset Beach State Park, just a short drive away, is another great option for a family day out, with its long sandy beach, playground, and nature trails.
  • What are the best Airbnb and holiday rentals in Madison, CT?

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

    You'll find the best deals on vacation rentals in the shoulder seasons, from April to May and September to October, when the weather is still pleasant but the crowds are smaller. If you want to experience the summer buzz, then book your rental in June, July or August, but be prepared to pay a premium.
  • What are the most popular Airbnbs in Madison, CT?

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

    A walk along the scenic coastline is a great way to enjoy Madison without spending any money. The Madison Green is also a lovely spot for a picnic lunch, and there are plenty of free events and activities taking place throughout the year.
  • What are the best holiday rentals with a pool in Madison, CT?

  • What are the best restaurants with local dishes in Madison, CT?

    Try the Lobster Roll at the Madison Beach Cafe, or the New England Clam Chowder at the The Griswold Inn. Both are classic local dishes, and they're delicious.
  • What are the best rentals for families and kids in Madison, CT?

  • What are the best walking or cycling routes in Madison, CT?

    The Shoreline Greenway Trail is a great option for both walking and cycling, offering stunning views of the Long Island Sound. The Madison Green is a lovely spot for a leisurely stroll, and there are plenty of quiet residential streets perfect for a bike ride.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

    Family House Near Hammonasset Beach State Park and Sundrenched 5 Br Home W/ Private Dock Near Beaches are the best holiday rentals or Airbnb with a jacuzzi in Madison, CT.

  • Are there pet-friendly attractions in Madison, CT?

    Yes, the Madison Beach is pet-friendly, and there are plenty of dog-walking trails in the area. The Hammonasset Beach State Park also welcomes dogs, but they must be kept on a leash.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy than a hotel room, and they're often more affordable, especially for families or groups. You'll also have access to a kitchen, which can save you money on dining out.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison has several public parks with sports facilities, including tennis courts, basketball courts, and baseball fields. The Madison Beach is also a popular spot for swimming, kayaking, and paddleboarding.

Destinations nearby

Best Madison, CT holiday rentals with a balcony

Stunning Historic Waterfront Mansion With Pool - Madison, CT
Madison, CT
24/06 – 28/06
A$2156/nighttotal: A$8624 (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.
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included - Madison, CT
Madison, CT
02/08 – 07/08
A$542/nighttotal: A$2710 (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.
Bliss By The Sea - Cozy Beachside Escape - Madison, CT
10 1 review
Madison, CT
23/06 – 26/06
A$847/nighttotal: A$2541 (3 )

Bliss By The Sea - Cozy Beachside Escape

2 3
apartment , Clinton
This Clinton waterfront apartment, situated in the Harborview Beach Association community, offers easy walking or cycling access to the beach and proximity to local landmarks such as the Adam Stanton House and General Store Museum.
The two-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, Roku TVs, a spacious back deck with gas grill, and ample parking; enjoy nearby attractions like the Allis-Bushnell House and Museum and RJ Julia Booksellers.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.6 10 reviews
Madison, CT
24/06 – 28/06
A$905/nighttotal: A$3620 (4 )

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

4 8
apartment , Killingworth
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 parking

Remodeled 4 Br Waterfront Beach House With All The Comforts Of Home...and More! - Madison, CT
9.8 20 reviews
Madison, CT
11/07 – 18/07
A$817/nighttotal: A$5719 (7 )

Remodeled 4 Br Waterfront Beach House With All The Comforts Of Home...and More!

4 4
apartment , Clinton
This charming beach house is located directly on the sand in Clinton, just a short drive from the town centre. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has four bedrooms and one bathroom, comfortably accommodating eight guests. It includes a fully equipped kitchen, a private sandy beach, a rear porch with seating, and direct access to the beach.
Resort Style Getaway W/pool, Spa, Game Room & More - Madison, CT
9.9 119 reviews
Madison, CT
11/07 – 18/07
A$2231/nighttotal: A$15617 (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.
River Front Home Good For Family And Groups - Madison, CT
10 1 review
Madison, CT
11/07 – 18/07
A$3284/nighttotal: A$22988 (7 )

River Front Home Good For Family And Groups

1 4
house , East Haddam
This East Haddam riverfront property is a short walk from the Goodspeed Opera House, 29km from Wesleyan University, and 45km from Eastern Connecticut State University.
Sleeping up to 15 guests, this one-bedroom house boasts four bathrooms, a fully equipped kitchen, a jacuzzi, private parking, Wi-Fi, and a garden; enjoy river views and nearby water activities.
“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach - Madison, CT
9.9 82 reviews
Madison, CT
12/07 – 16/08
A$616/nighttotal: A$21560 (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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