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Best Vacation rentals and Airbnb offers in Madison, CT
9.9 14 reviews
Madison, CT
07/12 – 08/16
$444/nighttotal: $15540 (35 )
Walk To The Water - Beach House With Views!
1 3
apartment , Guilford
This Mulberry Point home, less than two miles from downtown Guilford and near numerous hiking trails, offers a quiet beach community setting. This recently renovated two-bedroom house features a separate office, a fully equipped kitchen with high-end appliances, a private deck with a gas grill, a one-car garage with laundry facilities, and accommodates up to four guests.
9.5 205 reviews
Madison, CT
08/02 – 08/07
$403/nighttotal: $2015 (5 )
Postcard Cabins Machimoodus, Outdoor Collection By Marriott Bonvoy
2 4
cabin , East Haddam
This East Haddam cabin rental is conveniently located in a regional park, 0.7 miles from Machimoodus State Park and within 6 miles of the Goodspeed Opera House and Comstock Bridge. The pet-friendly cottage features a kitchenette with a stovetop, a private shower, a desk, a patio, and free parking; nearby attractions include Gillette Castle State Park and Cockaponset State Forest.
8.7 6 reviews
Madison, CT
08/24 – 08/27
$152/nighttotal: $456 (3 )
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.
Madison, CT
07/11 – 07/18
$628/nighttotal: $4396 (7 )
Guilford Shoreline Private Home
1 4
apartment , Guilford
This apartment is located in the heart of Guilford, just a short walk from the waterfront, the Norman Rockwell green, and 20 restaurants. The charming town offers a mix of history, culture, and outdoor activities, making it a perfect destination for travelers. This rental has two bedrooms and two bathrooms, comfortably accommodating up to five guests. The apartment features a fully equipped kitchen, air conditioning, a private backyard, and access to a fitness center and parking.
9.8 6 reviews
Madison, CT
08/02 – 08/07
$467/nighttotal: $2335 (5 )
The Beach Nest-lux Cottage Steps To The Beach
2 4
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.
9.9 32 reviews
Madison, CT
06/24 – 06/28
$870/nighttotal: $3480 (4 )
Zaku’s Lake House
1 8
apartment , Clinton
This 5-bedroom, 2-bathroom rental is located in Clinton, offering a peaceful escape with a private backyard and a full deck overlooking a lake. Guests consistently rate the location, cleanliness, and overall experience as excellent. The spacious home comfortably accommodates up to 10 guests. Enjoy a fully equipped kitchen, air conditioning, a BBQ, a fire pit, and stunning lake views from the deck.
9.8 27 reviews
Madison, CT
07/11 – 07/18
$772/nighttotal: $5404 (7 )
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.
4 4
apartment , Durham
This Durham vacation home is conveniently located near Millers Pond State Park (1.4 miles) and within 6 miles of Ron McCutcheon Park, Tri-Mountain State Park, Lyman Orchards, and Lyman Meadow Golf Club. This spacious four-bedroom house, sleeping up to eight guests, features a fully equipped kitchen, a fireplace, barbecue grills, and a terrace—perfect for families seeking outdoor recreation near Durham's parks and orchards.
9.8 48 reviews
Madison, CT
07/11 – 07/18
$427/nighttotal: $2989 (7 )
Relaxing Summer Rental, Walking Distance To The Beach, Short Ride To The Outlets
3 4
apartment , Westbrook
This Westbrook vacation home is located just a short walk from Westbrook Town Beach and a short drive from Tanger Outlets, offering a peaceful retreat in a convenient location. Guests consistently rate this property as excellent, highlighting its comfortable and well-equipped nature. The 1250 square foot house has three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a patio, a garden, a barbecue grill, air conditioning, internet access, and parking.
9.9 296 reviews
Madison, CT
08/24 – 08/27
$325/nighttotal: $975 (3 )
Charm + Location. Walk To Beach, Town, & Harbor.
1 2
apartment , Guilford
This charming cottage is conveniently located in the heart of Guilford, within easy walking distance of the town green, harbor, and beach. It consistently receives excellent ratings for location, cleanliness, and overall experience. The cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, a screened porch with games, a large side yard with a hammock and lawn furniture, and additional outdoor activities like bikes, yard games, and beach gear.
10 18 reviews
Madison, CT
07/11 – 07/18
$659/nighttotal: $4613 (7 )
New England Shoreline Charm, Private Beach Access
1 4
apartment , Madison
Summersalt, a Madison beach house, is located a short distance from a private beach ideal for swimming and relaxation. This three-bedroom, 1.5-bathroom rental sleeps eight guests and boasts a well-equipped kitchen with appliances including a Keurig, Crockpot, Instant Pot, fridge, freezer, microwave, and dishwasher, plus an enclosed porch, outdoor shower, grill, and patio.
Madison, CT
06/24 – 06/28
$1137/nighttotal: $4548 (4 )
New & Updated Coastal Home, Steps To The Sound -Sleeps 10 - Hot Tub - Central Ac
4 8
apartment , Madison
This Madison vacation home in Madison Center offers direct access to the Long Island Sound and is a 0.5-mile walk to East Wharf Beach, with proximity to West Wharf Beach and Surf Club Beach. This 4-bedroom, 2-bathroom apartment accommodates up to 10 guests with central air conditioning, a hot tub, fire table, outdoor grill, and a screened-in porch, providing a comfortable stay near attractions like the Allis-Bushnell House and Museum.
9.9 119 reviews
Madison, CT
07/11 – 07/18
$1568/nighttotal: $10976 (7 )
Resort Style Getaway W/pool, Spa, Game Room & More
5 4
apartment , East Haddam
This East Haddam apartment is just one mile from the charming East Haddam Center, offering easy access to the Connecticut River, Gillette Castle, and the town beach. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This spacious 5-bedroom home, with a floor area of 4500 square feet, comfortably accommodates up to 14 guests. Enjoy a private resort-style patio with a pool, hot tub, fireplace, and grill, along with a game room featuring a pool table, ping pong table, and arcade basketball.
Best Madison, CT vacation rentals with a balcony
Madison, CT
06/24 – 06/28
$1516/nighttotal: $6064 (4 )
Stunning Historic Waterfront Mansion With Pool
5 8
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.
9.0 2 reviews
Madison, CT
08/02 – 08/07
$1247/nighttotal: $6235 (5 )
Quarry House: Mid-century Modern
4 4
apartment , Haddam
This Haddam, Connecticut home, known as the Quarry House, sits atop a hill near the Connecticut River, offering easy access to attractions like the Goodspeed Opera House and the East Haddam Historical Society Museum. The 2170-square-foot mid-century modern residence boasts four bedrooms, three bathrooms, and accommodates eight guests, featuring a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and proximity to the Sundial Herb Garden and Kidcity Children's Museum.
Madison, CT
08/02 – 08/07
$381/nighttotal: $1905 (5 )
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included
1 4
apartment , Westbrook
This 1-bedroom, 1-bathroom apartment in Westbrook Center is located 4 minutes from West Beach and less than 1 mile (approximately 5,280 feet) from Westbrook Outlets, offering central access to Route 1 for day trips and proximity to attractions like the Connecticut Valley Railroad State Park. This 540 square foot dwelling accommodates up to 4 guests with air conditioning, a full kitchen including a dishwasher, and off-street parking with a Level 2 EV charger.
9.4 10 reviews
Madison, CT
07/11 – 07/18
$427/nighttotal: $2989 (7 )
Now Has Tv + Linens - Relaxing 4-bedroom Cottage In Westbrook, Ct At West Beach
4 4
cottage , Westbrook
This charming cottage is located in Westbrook Center, a short walk from West Beach and about 1.1 miles from the Shoreline East train station. It's a great option for families or groups looking for a comfortable and convenient place to stay near the beach. The cottage has received excellent user ratings, so you can be sure it's a good choice. The cottage has four bedrooms and two bathrooms, with enough space to comfortably accommodate seven guests. Enjoy the outdoors with a protected porch, screened-in sleeping porch, enclosed side porch, and outdoor shower, as well as a large lawn perfect for family gatherings.
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 20 reviews
Madison, CT
06/24 – 06/28
$834/nighttotal: $3336 (4 )
Whispering Meadow House
1 8
apartment , Guilford
This spacious Guilford home, sleeping eight, boasts four bedrooms, three bathrooms, and a fully equipped kitchen including a dishwasher and microwave. The house features a large open-concept great room, a jacuzzi, outdoor amenities such as a Weber grill and smoker, and ample parking; precise Guilford location details are unavailable.
10 7 reviews
Madison, CT
07/12 – 08/16
$829/nighttotal: $29015 (35 )
Private Beach, 3 Bedroom House Right On The Water
1 3
house , Clinton
This Clinton apartment is located in Kelsey Point, a short walk or bike ride from Hammock Beach and a mile from the town center. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment has three bedrooms and one bathroom, comfortably sleeping eight guests. Enjoy the private beach access, stunning ocean views, and outdoor amenities, including a BBQ grill, outdoor table, hammock, and screened porch.
9.8 26 reviews
Madison, CT
07/15 – 07/18
$1269/nighttotal: $3807 (3 )
Waterside Retreat! 4br/3ba With Private Dock/views
1 11
apartment , Clinton
Waterside, a historic family home in Clinton, Connecticut, is located steps from Clinton Town Beach and offers direct access to the Hammock River with a private dock. This four-bedroom, three-bathroom house sleeps eight guests and features a gourmet kitchen with Wolf Sub-Zero appliances, a waterfront patio with a grill and fire pit, and abundant amenities including beach gear and fast WiFi.
9.7 48 reviews
Madison, CT
07/11 – 07/18
$383/nighttotal: $2681 (7 )
Tranquil Lakefront Home @ Hidden Lake
1 4
apartment , Haddam
This lakefront house in Haddam is just a short drive from the town center and its historic landmarks, offering a peaceful retreat on Hidden Lake. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. The house has four bedrooms and can comfortably accommodate up to eight guests, making it ideal for families or groups. Enjoy the lake views from the three-season room, relax by the fire pit, and take advantage of the spacious yard, dedicated workspace, and ample parking.
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
9.8 52 reviews
Madison, CT
08/02 – 08/07
$554/nighttotal: $2770 (5 )
Beach Sanctuary On The Long Island Sound
1 4
apartment , Guilford
This Guilford, Connecticut island home boasts stunning Long Island Sound views, a short drive from Guilford's town green, train station, and a 20-minute drive to New Haven and Yale University. The newly renovated mid-century modern house features two queen bedrooms, a sofa bed, a full kitchen with dishwasher, a private association beach, outdoor patio with grill and firepit, and a game room with ping pong.
10 15 reviews
Madison, CT
07/11 – 07/18
$345/nighttotal: $2415 (7 )
Enjoy A Taste Of New England In Historic Guilford Ct
2 4
apartment , Guilford
This charming house is located in the heart of Guilford, within easy walking distance of the Guilford Art Center, Hyland House Museum, and Bishops Orchard and Winery. Guests rave about the excellent location and comfortable accommodations. This vacation home features two bedrooms, a sofa bed, and can comfortably sleep up to four guests. The fully equipped kitchen, private patio, and garden provide everything you need for a relaxing and enjoyable stay.
10 1 review
Madison, CT
08/02 – 08/07
$694/nighttotal: $3470 (5 )
Bliss By The Sea - Cozy Beachside Escape
2 4
apartment , Clinton
This Clinton waterfront apartment, located within the Harborview Beach Association, offers easy access to Harborview Beach and is a short walk or bike ride from the Adam Stanton House and General Store Museum. This single-level rental boasts two bedrooms, one bathroom, and sleeps four guests comfortably, featuring a fully equipped kitchen, in-unit laundry, a spacious deck, fenced yard, gas grill, and Roku TV with Wi-Fi.
10 13 reviews
Madison, CT
08/24 – 08/27
$240/nighttotal: $720 (3 )
Quiet Killingworth Rental W/ Deck & Grill!
1 2
apartment , Killingworth
This Killingworth seaside rental is conveniently located within 9 miles of attractions like the Sundial Herb Garden and Chatfield Hollow State Park. This 960-square-foot, two-bedroom, one-bathroom apartment sleeps four and features a fully equipped kitchen, in-unit games and books, and on-site parking and playground access.
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.
Madison, CT
07/11 – 07/18
$1599/nighttotal: $11193 (7 )
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.
4 4
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.
9.8 10 reviews
Madison, CT
06/24 – 06/28
$2123/nighttotal: $8492 (4 )
The Killingworth Estate
4 8
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.
10 14 reviews
Madison, CT
06/27 – 07/04
$930/nighttotal: $6510 (7 )
The Modernist | Patio & Pool | Beach (5-min Drive)
1 4
apartment , Madison
This modern house is located in Madison, just a short drive from Hammonasset Beach and the town center. It is a peaceful neighborhood with easy access to local shops, restaurants, and attractions. The house has four bedrooms and four bathrooms, comfortably accommodating up to eight guests. It includes a chef's kitchen, a spacious patio, a swimming pool, and a fire pit for outdoor enjoyment.
Madison, CT
07/12 – 08/16
$147/nighttotal: $5145 (35 )
Stay Aboard Mini-expedition Trawler Mary South
2 3
boat , Clinton
The Mary South, a unique mini-expedition ship accommodation, is docked at Clinton Yacht Haven, offering a waterfront stay a short distance from Hammonnasset Beach and State Park. This vessel provides 2 bedrooms and 2 bathrooms for up to 4 guests, featuring air conditioning, internet, a kitchen, and access to the yacht haven's swimming pool and clubhouse.
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.
10 55 reviews
Madison, CT
06/24 – 06/28
$1320/nighttotal: $5280 (4 )
Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck.
4 8
apartment , Guilford
9.6 69 reviews
Madison, CT
08/24 – 08/27
$243/nighttotal: $729 (3 )
Cozy Garden Apartment Along The Shoreline
1 2
apartment , Guilford
8.8 6 reviews
Madison, CT
07/11 – 07/18
$443/nighttotal: $3101 (7 )
Adorable Cottage With Cottage Porch, Walk To Water & Town
2 4
cottage , Westbrook
Madison, CT
06/27 – 07/04
$7202/nighttotal: $50414 (7 )
Grace Island. \Nprivate Island! Vacations, Getaways, Weddings & Special Events.
11 4
apartment , Branford
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.
Madison, CT
06/24 – 06/28
$733/nighttotal: $2932 (4 )
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!
4 8
apartment , Clinton
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.
