Best Holiday rentals and Airbnb offers in Madison, CT
8.0 1 review
Madison, CT
24/08 – 27/08
SG$251/nighttotal: SG$753 (3 )
Walk To Coast! Convenient Cottage In Dtwn Madison
1 2
apartment , Madison
This apartment is located in downtown Madison, offering walkable access to East Wharf Beach Park and Seaview Beach, and is within 1 kilometre of the Shoreline Greenway Trail. This 51 square meter, one-bedroom flat accommodates up to four guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and a washer/dryer, with step-free entry to the two-story studio cottage.
9.9 44 reviews
Madison, CT
27/06 – 04/07
SG$774/nighttotal: SG$5418 (7 )
The Farmhouse Stay
1 4
apartment , Haddam
The Farmhouse Stay is situated in Haddam, just a short drive from the Connecticut River and the historic Haddam Meadows State Park, offering a peaceful setting surrounded by nature. The property has received excellent ratings for its cleanliness, location, and overall experience. The two-bedroom, two-bathroom house can comfortably accommodate up to six guests and features a well-equipped kitchen, laundry room, and a spacious garden. Guests can enjoy a range of activities, including hiking, kayaking, and exploring the nearby historic sites.
9.6 15 reviews
Madison, CT
27/06 – 04/07
SG$619/nighttotal: SG$4333 (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.
10 3 reviews
Madison, CT
24/08 – 27/08
SG$223/nighttotal: SG$669 (3 )
Walk To Coast! Convenient Cottage In Dtwn Madison
1 2
apartment , Madison
This studio apartment in Madison is located behind a well-regarded French restaurant, offering a walkable neighbourhood with easy access to local attractions. This self-contained unit accommodates up to four guests with a queen bed and a queen sleeper sofa, featuring a private balcony, a Smart TV, reserved parking, and a Pack 'n Play for families.
10 7 reviews
Madison, CT
12/07 – 16/08
SG$1066/nighttotal: SG$37310 (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.
10 7 reviews
Madison, CT
02/08 – 07/08
SG$411/nighttotal: SG$2055 (5 )
The Little Cottage On The Ct River
1 4
cottage , Haddam
This Haddam cottage is situated near the Connecticut River and the Connecticut Valley Railroad State Park Trail, within walking distance of the Goodspeed Opera House and East Haddam Historical Society and Museum. The self-catering property sleeps four guests in one bedroom with one bathroom, and includes a fully equipped kitchen, laundry facilities, free Wi-Fi, parking, and air conditioning.
10 1 review
Madison, CT
02/08 – 07/08
SG$1255/nighttotal: SG$6275 (5 )
Beachside Bliss W/ Game Room, Gym & Golf Green
3 4
apartment , Westbrook
This three-bedroom flat in Westbrook, CT, offers direct beach access and is located 2 kilometres from the town centre and 3.2 kilometres from Westbrook Town Beach. This accommodation, suitable for six guests, boasts a private garden with a putting green and fire pit, a games room with arcade machines, and a home gym, all complemented by high-speed Wi-Fi for work or leisure.
9.4 10 reviews
Madison, CT
12/07 – 16/08
SG$476/nighttotal: SG$16660 (35 )
Now Has Tv + Linens - Relaxing 4-bedroom Cottage In Westbrook, Ct At West Beach
4 3
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.
Madison, CT
24/08 – 27/08
SG$319/nighttotal: SG$957 (3 )
Quiet Killingworth Rental W/ Deck & Grill!
1 2
apartment , Killingworth
This one-bedroom flat is situated in Deep River, just 19 kilometres from Killingworth, and is a short drive from the Goodspeed Opera House and Wesleyan University. The apartment is located in a peaceful area, offering a tranquil escape from the hustle and bustle. The 89 square metre flat has one bedroom and one bathroom, comfortably accommodating two guests. It features air conditioning, free Wi-Fi, a fully equipped kitchen with a fridge and microwave, a shared patio and grill, and cable TV.
9.9 81 reviews
Madison, CT
24/08 – 27/08
SG$220/nighttotal: SG$660 (3 )
A Peaceful Perch
1 2
apartment , Killingworth
This Killingworth studio apartment boasts a unique location on River Road, overlooking a glacial rock formation, less than 16km from Hammonasset Beach State Park and a short drive from Madison's amenities. The self-catering apartment offers a well-equipped kitchenette with fridge and microwave, sleeps two guests, and features a private deck with nature views, benefitting from excellent user ratings for cleanliness and location.
9.8 11 reviews
Madison, CT
07/09 – 30/09
SG$582/nighttotal: SG$13386 (23 )
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger
4 2
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.
10 56 reviews
Madison, CT
11/12 – 12/12
SG$1054/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.
Best family friendly Madison, CT holiday rentals
Among the 105 accommodations in Madison, CT, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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
What are the top family-friendly attractions in Madison, CT?
The most popular family-friendly attractions are the Madison Beach, the Hammonasset Beach State Park, and the Madison Surf Club. The beach offers a playground, and Hammonasset has a large, sandy beach, a playground, and a nature center, while the Surf Club is perfect for a family day out with its swimming pool and tennis courts.
What are the best Airbnb and vacation rentals in Madison, CT?
When is the best time to book a vacation rental in Madison, CT?
The best time to book a vacation rental is in the summer months, from June to August, as this is when the weather is best and the town is at its most lively. But if you're looking for a quieter experience, you could consider visiting in the spring or autumn.
What are the best budget-friendly activities in Madison, CT?
For a budget-friendly day out, head to the Hammonasset Beach State Park. It's a beautiful park with a long sandy beach, a playground, and a nature center. It's a great place to spend a day enjoying the outdoors without spending a lot of money.
What are the best vacation rentals with a pool in Madison, CT?
What are the best restaurants with local dishes in Madison, CT?
For local dishes, you'll want to try the Lobster Roll at The Lobster Shack, or the clam chowder at The Madison Beach Hotel. These are both classic New England dishes and are sure to satisfy your taste buds.
What are the best rentals for families and kids in Madison, CT?
What are the best walking or cycling routes in Madison, CT?
The Madison Green is a great place to start a walk or cycle. You can also explore the coastal path along the Sound, or head inland and explore the scenic backroads.
What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?
Are there pet-friendly attractions in Madison, CT?
Yes, the Hammonasset Beach State Park is pet-friendly. You can bring your dog to the beach and enjoy a walk along the shore. The park also has a dog park where your furry friend can run around off-leash.
What are the benefits of choosing a vacation rental in Madison, CT?
Vacation rentals offer more space and privacy than hotels, and you can often find rentals with amenities like kitchens and laundry facilities. They're also a great option for families or groups of friends travelling together.
What are the top sports attractions and facilities in Madison, CT?
Madison is known for its sailing, and there are several sailing clubs in the area. The Madison Surf Club offers tennis courts, a swimming pool, and a fitness center. If you're looking for a more casual activity, there's a public tennis court at the Madison Green.
Destinations nearby
Best Madison, CT holiday rentals with a balcony
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.
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.
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.
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
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.
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.
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.
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.