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Best Vacation rentals and Airbnb offers in Madison, CT
Madison, CT
06/20 – 08/20
$6627/nighttotal: $2823102 (426 )
Grace Island. \Nprivate Island! Vacations, Getaways, Weddings & Special Events.
11 2
apartment , Branford
This unique 11-bedroom island hotel is located in Branford, Connecticut, near Farm River State Park and West Rock Ridge State Park, and offers a natural beauty that is second to none. It features a floor area of 6500 square feet and can accommodate up to 22 guests. The island offers a wide range of amenities, activities, and features, including a dishwasher, terrace/balcony, garden, concierge, tennis court, games, water sports, and fishing gear. It also boasts full catering and dedicated chefs, freshly caught local seafood, and close proximity to Stony Creek Museum and Hyland House Museum.
Madison, CT
06/23 – 06/26
$321/nighttotal: $963 (3 )
The Connecticut Cottage Historic Modern Charm
2 3
cottage , Clinton
This restored 1790s stone house in Clinton offers a prime shoreline location, just a 5-minute drive to Clinton Outlets and Town Beach, and within walking distance of the Allis-Bushnell House and Museum and Hyland House Museum. This cottage accommodates up to 4 guests in 2 bedrooms and 2 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking, with easy access to Madison Beaches (10 miles), Old Saybrook Historic Downtown (15 miles), Mystic Seaport (30 miles), and New Haven (20 miles).
10 37 reviews
Madison, CT
11/22 – 11/29
$289/nighttotal: $2023 (7 )
Charming Madison, Ct Carriage House Ocean Rental
1 2
apartment , Madison
This charming cottage is located just four houses from the water in Madison, Connecticut, within easy walking distance of three town beaches, the Madison Beach Club, and the town center. Guest reviews consistently praise the cottage's excellent location, cleanliness, and overall experience. The cottage features a private carriage house with all-new furniture, a sunny porch, and one car parking. Enjoy a comfortable stay with amenities like air conditioning, a fully equipped kitchen, and a queen sleeper in the family room, perfect for a getaway with up to four guests.
9.8 6 reviews
Madison, CT
06/23 – 06/26
$445/nighttotal: $1335 (3 )
The Beach Nest-lux Cottage Steps To The Beach
2 3
apartment , Clinton
This charming cottage is located just steps from the beach on Shore Rd in Clinton, offering easy access to the sand and surf and minutes away from the town center and Connecticut shoreline attractions. The cottage is in a peaceful neighborhood with easy access to the town's attractions and the beautiful Connecticut shoreline. This cozy cottage features two bedrooms and one bathroom, comfortably accommodating up to five guests. The cottage offers modern amenities, including a fully equipped kitchen, a washer and dryer, a dishwasher, and air conditioning, as well as access to the internet and parking for two vehicles.
8.7 6 reviews
Madison, CT
11/22 – 11/29
$115/nighttotal: $805 (7 )
Stylish Modern Tiny Stay Steps From The Ocean
1 2
house , Clinton
This modern guest house in Clinton is steps from the beach and a short walk from local shops. The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, Wi-Fi, parking, and a garden.
9.6 9 reviews
Madison, CT
11/22 – 11/29
$501/nighttotal: $3507 (7 )
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard!
3 2
apartment , Madison
This Madison seaside home, less than 1.2 miles from Hammonasset Beach State Park, Allis-Bushnell House, and Scranton Memorial Library, offers convenient access to local attractions and amenities. This 4000-square-foot vacation rental boasts three bedrooms, three bathrooms, and accommodates six guests, featuring a fully equipped kitchen, garden, patio, and gas grills.
Madison, CT
11/22 – 11/29
$245/nighttotal: $1715 (7 )
Walk To Coast! Convenient Cottage In Dtwn Madison
1 2
studio , Madison
This downtown Madison cottage is located 1.4 miles from Hammonasset Beach and within driving distance of Thimble Islands and Yale University. This one-bedroom, one-bathroom apartment offers 550 square feet of living space, can accommodate up to 7 guests, and includes a fully equipped kitchen with a fridge and microwave, air conditioning, WiFi, and on-site laundry.
9.7 19 reviews
Madison, CT
11/22 – 11/29
$437/nighttotal: $3059 (7 )
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard!
3 2
apartment , Madison
This renovated three-bedroom house in Madison, CT, is located two miles from Hammonasset Beach State Park and a short drive from Bishop's Orchards. This three-bathroom home sleeps six guests and features a fully equipped kitchen with a Keurig coffee maker, a fireplace, flat-screen TVs, a private yard with a deck, fire pit, and gas grill, plus driveway parking for three cars.
Madison, CT
06/23 – 06/26
$459/nighttotal: $1377 (3 )
Tranquil Two Bedroom Home Near Shoreline
1 3
apartment , Madison
This Madison rental is conveniently located near Shoreline beaches, restaurants, and shops, making it easy to explore the city. The home is perfect for a family or group of friends with two bedrooms, one bathroom, and a guest capacity of four. The home features a fully equipped kitchen, a living room with a grand piano, a sitting room, a dining room, a back deck with a patio set and a gas BBQ grill, and central air conditioning. Enjoy a relaxing evening on the deck or spend time enjoying the beautiful piano.
Madison, CT
06/20 – 08/20
$728/nighttotal: $310128 (426 )
Gorgeous Connecticut Beachhouse ~
2 2
apartment , Guilford
This waterfront apartment is located just a 5-minute walk from Guilford Town Green, offering easy access to shops, restaurants, and cultural attractions. The area is charming and offers a peaceful escape from the hustle and bustle of city life. The apartment has 2 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy stunning water views, multiple decks for outdoor living, a gourmet kitchen, a master suite with a Jacuzzi tub, and ample parking for 5 cars.
10 2 reviews
Madison, CT
06/23 – 06/26
$2757/nighttotal: $8271 (3 )
Hollow Brook Estate
4 3
apartment , Killingworth
This 4-bedroom, 2-bathroom Killingworth vacation rental sits on a secluded 70-acre lakefront estate, offering a private natural setting near the Deacon John Grave House and within reasonable proximity to Madison, CT. This expansive estate features a pool with a waterfall, private tennis, volleyball, and bocce courts, an outdoor kitchen with a pizza oven, and a separate guest house with a commercial kitchen, game room, and weight room, accommodating up to 12 guests.
9.9 32 reviews
Madison, CT
11/22 – 11/29
$197/nighttotal: $1379 (7 )
Riverfront Antique Cabin In The Heart Of Madison
1 2
cabin , Madison
This Madison, Maine cabin sits on the Neck River, 1.5 miles from Grass Island and 2 miles from downtown Madison's beaches, shops, and restaurants. This two-bedroom, one-bathroom cottage sleeps four, offering a full kitchen, air conditioning, a stone porch perfect for fishing, and kayak access to the river, plus on-site ping pong and games.
Best Madison, CT vacation rentals with a balcony
9.6 10 reviews
Madison, CT
11/22 – 11/29
$483/nighttotal: $3381 (7 )
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger
4 2
apartment , Killingworth
This waterfront vacation home in Killingworth is located near Cockaponset State Forest and Sundial Herb Garden, offering easy access to scenic hiking trails and unique botanical attractions. It has earned excellent user ratings, making it a popular choice for travelers. This 1300 square foot house comfortably sleeps up to 10 guests in its 4 bedrooms and 1 bathroom. Enjoy the convenience of a fully equipped kitchen, air conditioning, a private terrace, a garden, and parking, perfect for relaxing and exploring the surrounding area.
10 55 reviews
Madison, CT
11/22 – 11/29
$1021/nighttotal: $7147 (7 )
Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck.
4 2
apartment , Guilford
This charming vacation home is located in Guilford, directly across the street from a sandy beach with a playground and within walking distance of the historic Guilford Green. The apartment has received excellent user ratings and is perfect for families and groups seeking a comfortable and convenient stay. This spacious 4-bedroom, 3-bathroom rental offers 2,700 square feet of living space and comfortably accommodates up to 8 guests. Enjoy a fully equipped kitchen, a wrap-around deck with outdoor dining, a huge backyard, a gas grill, and a variety of outdoor games, plus kayaks, ping pong and foosball tables, beach chairs and an umbrella, and a hot/cold outdoor shower.
Madison, CT
06/23 – 06/26
$1518/nighttotal: $4554 (3 )
Stunning Historic Waterfront Mansion With Pool
5 3
apartment , Clinton
This historic 5-bedroom house, formerly the Clinton Country Club Clubhouse, is located on the waterfront with direct views of Clinton Harbor and Meigs Point, less than a mile from downtown Clinton's shopping and dining. This waterfront home offers a private Gunite pool, multiple decks with water views, a chef's kitchen with Sub-Zero appliances and a Wolf Stove, two fireplaces, a wrap-around all-season porch, luxurious Captain's quarters on the third floor, and nanny quarters with a separate entrance, accommodating up to 10 guests.
Madison, CT
06/23 – 06/26
$1578/nighttotal: $4734 (3 )
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.
4 3
houseboat , Clinton
This houseboat in Clinton, CT, is docked at a prime location, offering easy access to RJ Julia Booksellers and Clinton Crossing Premium Outlets, just a short distance away. This four-bedroom, four-bathroom yacht accommodates up to eight guests, featuring a king bed, queen bed, and two twin beds, along with a flybridge bar and an aft deck dining area perfect for entertaining.
Guest-Favorite Family Vacation Rentals in Madison, CT
Find the perfect family vacation rental or Airbnb in Madison, CT with plenty of room to spread out near local beaches.
10 89 reviews
Madison, CT
11/22 – 11/29
$212/nighttotal: $1484 (7 )
The Barn By The Sound
1 2
studio , Madison
This studio apartment is located in a quiet, historic neighborhood in Madison, just a block from Long Island Sound and the Boston Post Road. The studio has received excellent ratings for cleanliness, location, and user experience. This one-bedroom apartment comfortably sleeps two guests. It features a modern kitchen with a gas cooktop, microwave, oven, refrigerator, dishwasher, and a Roku smart TV. Guests can enjoy a sunny bench outside the barn, perfect for morning coffee and planning their day.
9.8 11 reviews
Madison, CT
11/22 – 11/29
$503/nighttotal: $3521 (7 )
Coastal Getaway On Marsh Near Beach, Town, Trails
1 2
apartment , Guilford
This three-bedroom, two-bathroom Guilford vacation rental is located on a quiet cul-de-sac, one mile from Guilford Green and a short drive from Hammonasset Beach State Park and the train station. The 3+ bedroom home features an open floor plan, sleeps eight guests, includes a fenced yard, two-car garage, and amenities such as Wi-Fi, air conditioning, and a grill; enjoy birdwatching from the deck overlooking the marsh.
9.8 21 reviews
Madison, CT
11/22 – 11/29
$578/nighttotal: $4046 (7 )
Cheerful 4br Home-7 Min Walk To Private Beach
1 2
apartment , Madison
This Madison apartment rental in Kelsey Place offers a short walk to a private beach. The 4-bedroom, 3-bathroom home sleeps 10, features a 3-car garage, modern appliances, and a family-friendly layout with a large master suite and private balcony.
9.2 5 reviews
Madison, CT
11/22 – 11/29
$620/nighttotal: $4340 (7 )
Private Pool! Getaway, 14 Mi To Hammonasset Beach
4 2
apartment , Killingworth
This charming vacation home is located in Killingworth, a short drive from Hammonasset Beach State Park and Lyman Orchards Golf Course. It has received excellent user ratings, making it a popular choice for travelers. This 4-bedroom, 2-bathroom rental offers 2,030 square feet of space, comfortably accommodating up to 8 guests. Enjoy a private pool and terrace, a fully equipped kitchen, laundry facilities, and a fireplace.
Frequently Asked Questions about vacation rentals in Madison, CT
What are the top family-friendly attractions in Madison, CT?
The Madison Beach & Recreation Area is a great spot for families, with a playground, picnic areas, and a splash pad. The Hammonasset Beach State Park is another great option, with a large beach, hiking trails, and a nature center.
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 summer months (June to August) are the busiest time for tourism in Madison, so it's best to book your rental well in advance. If you're looking for a more affordable option, you could consider visiting in the shoulder seasons (spring and fall).
What events or festivals should visitors check out in and around Madison, CT?
The Madison Beach & Arts Festival in July is a popular event, featuring live music, art exhibits, and food vendors. The Madison Farmers Market takes place every Saturday from May to October, offering local produce and crafts.
What are the best vacation rentals with a pool in Madison, CT?
What are the best budget-friendly activities in Madison, CT?
Take a walk or bike ride along the Madison Shoreline Trail, enjoy a picnic at Hammonasset Beach State Park, or explore the Madison Historical Society Museum.
What are the best rentals for families and kids in Madison, CT?
What are the best restaurants with local dishes in Madison, CT?
For classic New England seafood, check out The Lobster Landing or The Griswold Inn. The Madison Beach Hotel offers a more upscale dining experience with beautiful views of the Long Island Sound.
What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?
What are the best walking or cycling routes in Madison, CT?
The Madison Shoreline Trail is a great option for a scenic walk or bike ride. It stretches for over 5 miles along the coast, offering views of the Long Island Sound and the surrounding coastline.
Are there pet-friendly attractions in Madison, CT?
Yes, many of Madison's parks and beaches are dog-friendly. Hammonasset Beach State Park has a designated dog beach area, and the Madison Green is also a great spot to walk your furry friend.
What are the benefits of choosing a vacation rental in Madison, CT?
Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
What are the top sports attractions and facilities in Madison, CT?
Madison has a number of sports facilities, including the Madison Beach & Recreation Area, which offers a variety of activities like tennis, basketball, and volleyball. The Hammonasset Beach State Park also has a number of hiking trails and a boat launch.
Destinations nearby
Best Madison, CT vacation rentals with parking
9.9 225 reviews
Madison, CT
11/22 – 11/29
$451/nighttotal: $3157 (7 )
1860's Colonial House Near Downtown And Beaches!
1 2
house , Madison
This charming 1860s Colonial home is located in Madison, just a short 17-minute walk from Hammonasset Beach and a quick drive to Thimble Islands, offering a peaceful escape from the hustle and bustle of downtown. The house consistently receives excellent ratings for its cleanliness, location, and overall experience. The home features four bedrooms and three bathrooms, providing ample space for families or groups of friends. Enjoy modern amenities like air conditioning, a fully equipped kitchen, a private terrace, a garden, and parking, perfect for a comfortable and relaxing stay.
10 4 reviews
Madison, CT
11/22 – 11/29
$366/nighttotal: $2562 (7 )
New Coastal Cottage 2 Miles To Beach + Lake Access
2 2
cottage , Clinton
This newly refurnished cottage in Clinton is located 2 miles from Hammonassett Beach and a short walk to Boulder Lake Beach, with downtown Clinton and Madison also within 2 miles. This 2-bedroom, 1-bathroom rental accommodates up to 6 guests and features air conditioning, a microwave, dishwasher, internet, and parking, with a screened-in porch and fire pit for outdoor enjoyment.
9.6 69 reviews
Madison, CT
11/22 – 11/29
$207/nighttotal: $1449 (7 )
Cozy Garden Apartment Along The Shoreline
1 2
apartment , Guilford
This one-bedroom apartment is located in Guilford, just 17 miles from New Haven's City Hall and 9.5 miles from Thimble Islands, offering a peaceful retreat close to attractions. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 4310 square foot apartment features a fully equipped kitchenette, a private patio with garden views, and a Jacuzzi for relaxation. Guests can enjoy amenities like a picnic area, complimentary Wi-Fi, private parking, and access to nearby windsurfing and fishing opportunities.
Madison, CT
11/22 – 11/29
$228/nighttotal: $1596 (7 )
Walk To Coast! Convenient Cottage In Dtwn Madison
1 2
apartment , Madison
This apartment is located in downtown Madison, within walking distance of East Wharf Beach Park and Seaview Beach, and is 2 miles from Hammonasset Beach State Park. This 550 square foot unit offers a queen bed and queen sleeper sofa for up to 4 guests, with amenities including a private balcony, on-site laundry, and step-free entry.
Neighborhoods and points of interest in Madison, CT
Check Out Vacation Rentals with a Pool in Madison, CT
A vacation rental with a pool in Madison, CT is the perfect amenity to complement your time spent by the water.
9.8 10 reviews
Madison, CT
11/22 – 11/29
$545/nighttotal: $3815 (7 )
Private Pool! Getaway, 14 Mi To Hammonasset Beach
4 2
apartment , Killingworth
This secluded vacation home is located in Killingworth, Connecticut, close to beaches, hiking trails, and lakes, making it a great base for exploring the area. Guests consistently rate the property excellent for its location, cleanliness, and overall experience. The home features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a private pool, a gas grill, a wood-burning fire pit, and a walking trail, perfect for relaxing and enjoying the outdoors.
9.8 10 reviews
Madison, CT
11/22 – 11/29
$1853/nighttotal: $12971 (7 )
The Killingworth Estate
4 2
house , Killingworth
This 67-acre lakefront estate is located in Killingworth, Connecticut, just a short drive from the charming town center and a scenic distance from the Connecticut shoreline. The property has earned excellent ratings for its location, cleanliness, and overall experience. The home features four bedrooms and three bathrooms, accommodating up to eleven guests. Enjoy a luxurious stay with private tennis, volleyball, and bocce courts, a pool with a waterfall, an outdoor kitchen with a pizza oven, multiple patios, decks, and gardens.
Madison, CT
11/22 – 11/29
$623/nighttotal: $4361 (7 )
Private Pool! Getaway, 14 Mi To Hammonasset Beach
4 2
house , Killingworth
This Killingworth house rental, a peaceful retreat located 13 miles from Wesleyan University and 15 miles from the Goodspeed Opera House, offers easy access to Connecticut attractions. The 2,030-square-foot home features four bedrooms, two bathrooms, accommodates up to 15 guests, and includes a private pool, Wi-Fi, and a fully equipped kitchen with modern appliances.
9.8 51 reviews
Madison, CT
11/22 – 11/29
$1327/nighttotal: $9289 (7 )
Waterfront Estate Home - Pool And Private Beach Pavilion - East
9 2
apartment , Madison
This charming summer home is located on Middle Beach Road in Madison, Connecticut, offering private waterfront access to Long Island Sound and a shared pool. It boasts excellent user, location, and cleanliness ratings. The property is comprised of two twin homes, offering privacy and ample space for everyone. This spacious vacation rental features nine bedrooms, a large living area, and a full kitchen, perfect for families or groups of friends. Guests can enjoy the private beach, the shared pool, and the beautiful views of Long Island Sound.
Discover Vacation Rentals by the Sea in Madison, CT
Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Madison, CT. Book your next shoreside stay today.
9.9 174 reviews
Madison, CT
06/23 – 06/26
$296/nighttotal: $888 (3 )
Cozy Cottage Near Downtown Clinton, Marina & Hammonasset Park
3 3
cottage , Clinton
10 1 review
Madison, CT
06/23 – 06/26
$672/nighttotal: $2016 (3 )
Bliss By The Sea - Cozy Beachside Escape
2 3
apartment , Clinton
9.8 17 reviews
Madison, CT
11/22 – 11/29
$439/nighttotal: $3073 (7 )
One Bedroom Apt-cristys Madison
1 2
apartment , Madison
9.8 53 reviews
Madison, CT
11/22 – 11/29
$418/nighttotal: $2926 (7 )
Cozy Beach Cottage Close To Everthing
1 2
apartment , Madison
Discover 5-Star Vacation Rentals in Madison, CT
Refined interiors and prime locations make these luxury waterfront vacation rentals in Madison, CT the ideal choice for your stay.
10 2 reviews
Madison, CT
11/22 – 11/29
$385/nighttotal: $2695 (7 )
Spacious Family Beach House
1 2
apartment , Madison
Best Vacation Rentals with a Steam Room in Madison, CT
Maximize your recovery with an on-site sauna, a standard feature at these premier Madison, CT vacation rentals.
9.9 174 reviews
Madison, CT
06/23 – 06/26
$296/nighttotal: $888 (3 )
Cozy Cottage Near Downtown Clinton, Marina & Hammonasset Park
