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

Welcome To Pleasant Valley House - Madison, CT
9.9 26 reviews
Madison, CT
11/12 – 12/12
A$878/nightfor 1 night

Welcome To Pleasant Valley House

1 6
apartment , Clinton
This three-bedroom, two-bathroom house in Clinton, Connecticut, is a six-minute drive from the beach and offers easy access to Hammonasset Beach State Park and other attractions.
Sleeping eight comfortably, this modern farmhouse boasts a fully equipped kitchen, separate dining room, living room, loft, and basement with washer/dryer; outside, there's a deck with a grill and ample parking.
The Killingworth Estate - Madison, CT
9.8 10 reviews
Madison, CT
24/06 – 28/06
A$3020/nighttotal: A$12080 (4 )

The Killingworth Estate

4 8
house , Killingworth
This 67-acre lakefront property is located in Killingworth, a short drive from the town centre and the Connecticut shoreline. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious house has four bedrooms and can sleep up to 11 guests. The property offers a range of amenities, including a swimming pool, tennis court, and a fully equipped kitchen.
Cozy Maple Tree Cabin - Situated On 6 Private Acres- Enjoy Nature - Madison, CT
10 56 reviews
Madison, CT
11/12 – 12/12
A$1167/nightfor 1 night

Cozy Maple Tree Cabin - Situated On 6 Private Acres- Enjoy Nature

3 6
cabin , Killingworth
This charming lodge is situated in a peaceful rural area of Killingworth, just a short drive from attractions like the Adam Stanton House and General Store, Connecticut Valley Railroad State Park Trail, and Hammonasset Beach State Park. It is a great base for exploring the local history and natural beauty of the area.
The lodge spans 158 square metres and comfortably accommodates up to 8 guests in its three bedrooms and two bathrooms. The lodge offers a fully equipped kitchen, modern amenities like free high-speed Wi-Fi and a smart TV, as well as an outdoor patio for relaxing and enjoying the fresh air.
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.

Best Madison, CT holiday rentals with a pool

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

The Modernist | Patio & Pool | Beach (5-min Drive) - Madison, CT
10 14 reviews
Madison, CT
27/06 – 04/07
A$1323/nighttotal: A$9261 (7 )

The Modernist | Patio & Pool | Beach (5-min Drive)

1 4
apartment , Madison
The Modernist is located in Madison, Connecticut, just 2.2 kilometres from Hammonasset Beach and 1.6 kilometres from the town centre. The property is situated in a peaceful residential area, close to shops, restaurants, and attractions.
This four-bedroom house can accommodate up to eight guests, with three king-size beds and one queen-size bed. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, and parking.
Stay Aboard Mini-expedition Trawler Mary South - Madison, CT
Madison, CT
12/07 – 07/06
A$191/nighttotal: A$63030 (330 )

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.
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.
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

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
24/08 – 27/08
A$2388/nighttotal: A$7164 (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.
Bliss By The Sea - Cozy Beachside Escape - Madison, CT
10 1 review
Madison, CT
02/08 – 07/08
A$988/nighttotal: A$4940 (5 )

Bliss By The Sea - Cozy Beachside Escape

2 4
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.
Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck. - Madison, CT
10 55 reviews
Madison, CT
02/08 – 07/08
A$2030/nighttotal: A$10150 (5 )

Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck.

4 4
apartment , Guilford
This apartment is located directly across the street from a sandy beach with a playground, offering stunning water views of Long Island Sound and is within walking distance of restaurants, bars, and shops. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has four bedrooms and three bathrooms, accommodating up to eight guests, and offers a spacious open plan layout over 251 square metres. It includes a fully equipped kitchen, a wrap-around deck, a garden, a spa, a tennis court, parking, and a range of amenities for a comfortable stay, including kayaks, beach chairs, and outdoor games.
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
A$533/nighttotal: A$3731 (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.

Best Madison, CT holiday rentals with parking

Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 4 reviews
Madison, CT
24/08 – 27/08
A$790/nighttotal: A$2370 (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.
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly! - Madison, CT
Madison, CT
24/06 – 28/06
A$1043/nighttotal: A$4172 (4 )

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

4 8
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.
The Millhouse Downtown Chester - Madison, CT
10 116 reviews
Madison, CT
02/08 – 07/08
A$771/nighttotal: A$3855 (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.
Relaxing Summer Rental, Walking Distance To The Beach, Short Ride To The Outlets - Madison, CT
9.8 48 reviews
Madison, CT
11/07 – 18/07
A$608/nighttotal: A$4256 (7 )

Relaxing Summer Rental, Walking Distance To The Beach, Short Ride To The Outlets

3 4
apartment , Westbrook
This holiday home is located in Westbrook Center, just a short walk from Westbrook Town Beach and a short drive from Tanger Outlets. It’s rated excellent by previous guests and is ideal for a relaxing escape.
The property is a spacious three-bedroom house with one bathroom, offering 116 square metres of living space and sleeping up to six guests. It comes with a fully equipped kitchen, a patio, and a garden, perfect for enjoying outdoor meals and relaxing evenings.
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