Holiday Rentals in Madison, CT

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Madison, CT holiday rentals
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Best Holiday rentals and Airbnb offers 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

Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck. - Madison, CT
10 55 reviews
Madison, CT
07/09 – 30/09
SG$1223/nighttotal: SG$28129 (23 )

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

4 2
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.
Welcome To Pleasant Valley House - Madison, CT
9.9 26 reviews
Madison, CT
11/12 – 12/12
SG$793/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.
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown. - Madison, CT
9.8 27 reviews
Madison, CT
02/08 – 07/08
SG$1129/nighttotal: SG$5645 (5 )

New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.

4 4
apartment , Durham
This Durham holiday home is situated approximately 2.3 kilometres from Millers Pond State Park, and within 10 kilometres of Ron McCutcheon Park and Tri-Mountain State Park, offering easy access to local recreational areas and Lyman Orchards.
The four-bedroom property sleeps eight guests, boasting three bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, a terrace, garden, parking, and free Wi-Fi; enjoy a comfortable stay with amenities such as a fireplace and barbecue facilities.
1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach - Madison, CT
Madison, CT
02/08 – 07/08
SG$681/nighttotal: SG$3405 (5 )

1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach

2 4
apartment , Westbrook
This ground-floor flat in Westbrook Centre offers convenient access, being a 4-minute drive from West Beach and less than 1 kilometre from Westbrook Outlets.
This 50 square metre apartment sleeps up to four guests and features two bedrooms, one bathroom, a kitchen with a dishwasher, air conditioning, and dedicated parking, serving as an ideal base for exploring the shoreline.

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
SG$1013/nighttotal: SG$35455 (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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 68 reviews
Madison, CT
07/09 – 30/09
SG$935/nighttotal: SG$21505 (23 )

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.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
27/06 – 04/07
SG$1984/nighttotal: SG$13888 (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.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 10 reviews
Madison, CT
07/09 – 30/09
SG$819/nighttotal: SG$18837 (23 )

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.

Frequently asked questions about holiday rentals in Madison, CT

Destinations nearby

Best Madison, CT holiday rentals with a balcony

Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included - Madison, CT
Madison, CT
02/08 – 07/08
SG$490/nighttotal: SG$2450 (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.
The Millhouse Downtown Chester - Madison, CT
10 116 reviews
Madison, CT
02/08 – 07/08
SG$697/nighttotal: SG$3485 (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.  \Nprivate Island!  Vacations, Getaways, Weddings & Special Events. - Madison, CT
Madison, CT
12/07 – 07/06
SG$8306/nighttotal: SG$2740980 (330 )

Grace Island. \Nprivate 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.
Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 4 reviews
Madison, CT
24/08 – 27/08
SG$714/nighttotal: SG$2142 (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.

Best Madison, CT holiday rentals with parking

Spectacular Lake Front Cabin Close To Ct Shoreline - Madison, CT
Madison, CT
27/06 – 04/07
SG$1456/nighttotal: SG$10192 (7 )

Spectacular Lake Front Cabin Close To Ct Shoreline

2 4
cabin , Guilford
This North Branford lodge is situated approximately 10km from Guilford town centre and attractions such as the Guilford Art Centre and Bill Miller's Castle.
The two-bedroom, one-bathroom self-catering property sleeps four guests and offers amenities including a fully equipped kitchen with dishwasher and microwave, laundry facilities, air conditioning, parking, and barbecue grills; nearby Orchard Hill Plaza provides further shopping options.
Relax In A Cabin By The Beach (Cottage No.1) - Madison, CT
9.5 29 reviews
Madison, CT
24/08 – 27/08
SG$301/nighttotal: SG$903 (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.
The Davis House - Madison, CT
9.8 67 reviews
Madison, CT
24/08 – 27/08
SG$453/nighttotal: SG$1359 (3 )

The Davis House

3 2
apartment , Guilford
This spacious three-bedroom house is located in a peaceful neighbourhood in Guilford, Connecticut, just 1.6 kilometres from the historic town green and 0.8 kilometres from Interstate 95. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has three bathrooms and can accommodate up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a large fenced garden, and parking. Guests can also enjoy outdoor activities such as hiking, biking, and kayaking, all within a short drive.
River Front Home Good For Family And Groups - Madison, CT
10 1 review
Madison, CT
27/06 – 04/07
SG$3016/nighttotal: SG$21112 (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.
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