This one-bedroom flat is situated in a peaceful neighbourhood just a short walk from the town green, placing you within easy reach of shops, restaurants, the train station, the marina, and Guilford beach. The property has received excellent ratings for its location, cleanliness, and overall experience. The flat is ideal for couples or solo travellers, offering a comfortable full-size bed and a fully equipped kitchen. Guests can enjoy free Wi-Fi, on-street parking, and a prime location in the heart of Guilford.
9.8 10 reviews
Madison, CT
23/06 – 26/06
$2632/nighttotal: $7896 (3 )
The Killingworth Estate
4 3
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.
9.9 174 reviews
Madison, CT
23/06 – 26/06
$414/nighttotal: $1242 (3 )
Cozy Cottage Near Downtown Clinton, Marina & Hammonasset Park
3 3
cottage , Clinton
This family-friendly cottage is located just 1.6km from Indian River Marina and the Adam Stanton House, and within 3.2km of Clinton Town Beach and Hammonasset Beach State Park. The cottage is highly rated by guests, with excellent reviews for location, cleanliness, and overall experience. The property offers 3 bedrooms and 1 bathroom across 93 square metres. Guests can enjoy a fully equipped kitchen, a patio for outdoor dining, a garden, and a barbecue grill, as well as modern amenities like air conditioning, internet, and a washing machine.
10 2 reviews
Madison, CT
23/06 – 26/06
$3853/nighttotal: $11559 (3 )
Hollow Brook Estate
4 3
apartment , Killingworth
This expansive 70-acre lakefront estate in Killingworth offers a secluded setting, conveniently located near Madison, CT, and attractions such as the Deacon John Grave House and Scranton Memorial Library. This luxurious holiday home boasts four bedrooms, accommodating up to twelve guests, and features private recreational facilities including tennis, volleyball, and bocce courts, alongside a pool with a waterfall and a dedicated guest house with a game room and weight room.
Madison, CT
20/06 – 20/08
$1017/nighttotal: $433242 (426 )
Gorgeous Connecticut Beachhouse ~
2 2
apartment , Guilford
This waterfront apartment is located just 5km from the Guilford Town Green, a charming area with shops, restaurants and regular events. The apartment is a 5-minute drive from the town centre. This two-bedroom, two-bathroom property can comfortably accommodate up to 6 guests. The apartment offers direct waterfront access with a stone pier for kayaking, stand-up paddleboarding, and fishing, along with multiple decks for outdoor dining and relaxing.
9.2 7 reviews
Madison, CT
23/06 – 26/06
$360/nighttotal: $1080 (3 )
Shoreline Oasis
1 3
apartment , Clinton
This Clinton city-centre apartment offers easy access to the waterfront, train station, and Lobster Landing, with Hammonassett State Park and Chamard Vineyards within a short 8km drive. The 51-square-metre self-contained flat comprises one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, Netflix/Hulu access, a terrace, and private parking.
9.4 7 reviews
Madison, CT
22/11 – 29/11
$460/nighttotal: $3220 (7 )
The Mermaids Cove
1 2
apartment , Madison
This Madison cottage, situated on a quiet, private street with direct beach access to the Long Island Sound, offers a peaceful retreat close to Madison town centre. Sleeping five guests, this three-bedroom, one-bathroom property boasts a full kitchen, fireplace, smart TV, patio with wheelchair access, screened porch, and a hybrid bicycle for guest use; enjoy the private beach and proximity to local restaurants and attractions.
9.6 9 reviews
Madison, CT
22/11 – 29/11
$700/nighttotal: $4900 (7 )
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard!
3 2
apartment , Madison
This Madison seaside property is situated less than 2km from Hammonasset Beach State Park, the Allis-Bushnell House and Museum, and the Scranton Memorial Library, with RJ Julia Booksellers and Anna Mia's also nearby. This 372 square metre house offers four bedrooms, three bathrooms, sleeps six guests, and boasts a fully equipped kitchen, terrace, garden, parking, and air conditioning.
Madison, CT
22/11 – 29/11
$319/nighttotal: $2233 (7 )
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.
Madison, CT
23/06 – 26/06
$1607/nighttotal: $4821 (3 )
New & Updated Coastal Home, Steps To The Sound -Sleeps 10 - Hot Tub - Central Ac
4 3
apartment , Madison
This four-bedroom, two-bathroom flat in Madison Centre offers direct access to the Long Island Sound with water views and is located just 800 metres from East Wharf Beach, with Madison town centre and other beaches also within easy reach. This recently updated apartment accommodates up to ten guests and features central air conditioning, a hot tub, fire table, and a screened-in porch, making it ideal for wedding guests with specific Thursday to Sunday September rental options.
Madison, CT
23/06 – 26/06
$1178/nighttotal: $3534 (3 )
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!
4 3
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.
Madison, CT
23/06 – 26/06
$582/nighttotal: $1746 (3 )
New Charming Coastal Bungalow Steps From The Beach
1 3
apartment , Madison
This newly remodelled two-bedroom flat offers exceptional proximity to the beach, just 152 metres away, and is conveniently situated 2.4 kilometres from downtown Madison, providing easy access to local shops and restaurants, whilst being mere minutes from Hammonasset Beach State Park. Accommodating up to six guests, this coastal getaway features two queen beds and a pull-out sofa, a full bathroom with a walk-in shower, private driveway parking for two vehicles, and is located in a quiet, walkable neighbourhood.
Best family friendly Madison, CT vacation rentals
Among the 105 accommodations in Madison, CT, here are the 4 best family friendly rentals
9.2 5 reviews
Madison, CT
22/11 – 29/11
$866/nighttotal: $6062 (7 )
Private Pool! Getaway, 14 Mi To Hammonasset Beach
4 2
apartment , Killingworth
This charming four-bedroom apartment in Killingworth is a 40-kilometre drive from Hammonasset Beach State Park and a 27-kilometre drive from the Lyman Orchards Golf Course and Farmers Market. It has received excellent user ratings and is perfect for families or groups looking for a comfortable and convenient base to explore the surrounding area. This spacious apartment offers 189 square metres of living space, comfortably accommodating up to eight guests. You'll enjoy a private pool and patio, covered parking, a fully equipped kitchen, a fireplace, a fire pit and barbecue grill, and a washer and dryer.
10 13 reviews
Madison, CT
22/11 – 29/11
$290/nighttotal: $2030 (7 )
Quiet Killingworth Rental W/ Deck & Grill!
1 2
apartment , Killingworth
This Killingworth seaside flat is situated 15km from attractions including the Sundial Herb Garden and Chatfield Hollow State Park. The 89 square metre self-catering apartment sleeps four, boasting a fully equipped kitchen, Wi-Fi, parking, and a playground nearby.
10 111 reviews
Madison, CT
22/11 – 29/11
$423/nighttotal: $2961 (7 )
Shabby Chic Retreat
1 2
apartment , Madison
Greenfield Cottage is located in a quiet neighbourhood in Madison, Connecticut, just 6.5km from Hammonasset State Park & Beach and close to Chatfield Hollow. The property enjoys excellent ratings for location, cleanliness, and overall user experience. This charming cottage offers a separate studio apartment with a private entrance and garden space for guests who desire privacy. The accommodation can comfortably sleep up to four people and comes equipped with a kitchen, a garden, parking, laundry facilities, and a keypad lock for easy access.
10 55 reviews
Madison, CT
22/11 – 29/11
$1427/nighttotal: $9989 (7 )
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.
Best Madison, CT vacation rentals with a pool
Among the 105 accommodations in Madison, CT, here are the 4 best rentals with a pool
10 68 reviews
Madison, CT
22/11 – 29/11
$1118/nighttotal: $7826 (7 )
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.
9.8 51 reviews
Madison, CT
22/11 – 29/11
$1855/nighttotal: $12985 (7 )
Waterfront Estate Home - Pool And Private Beach Pavilion - East
9 2
apartment , Madison
This summer house on Middle Beach Road in Madison, Connecticut is just a short distance from the town centre and offers private waterfront access to Long Island Sound. The property has received excellent ratings for user experience, location and cleanliness. The house is spread over 366 square metres and has nine bedrooms, comfortably sleeping 20 guests. It offers a range of amenities including a private beach, a swimming pool, a garden, parking, and a fully equipped kitchen.
Madison, CT
23/06 – 26/06
$2122/nighttotal: $6366 (3 )
Stunning Historic Waterfront Mansion With Pool
5 3
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.
Madison, CT
23/06 – 26/06
$2206/nighttotal: $6618 (3 )
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.
4 3
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.
Frequently Asked Questions about vacation rentals in Madison, CT
What should a first-time visitor not miss in Madison, CT?
For a first-time visit, you should definitely check out the Madison Beach & the charming shops and restaurants on Boston Post Road. The historic town green is also a must-see, with the iconic Madison Town Hall.
What are the best Airbnb and vacation rentals in Madison, CT?
Which neighborhood in Madison, CT should you consider for a vacation rental?
The area around the Madison Green is a great choice for a vacation rental. It's close to the beach, shops, and restaurants. Alternatively, the more residential neighbourhoods of North Madison or West Madison could be good choices if you prefer a quieter setting.
What are the top family-friendly attractions in Madison, CT?
The Hammonasset Beach State Park is a fantastic spot for families, with a large beach, a playground, and a nature centre. The Madison Surf Club is a great place to learn to surf or just enjoy the beach.
What are the best vacation rentals with a pool in Madison, CT?
When is the best time to book a vacation rental in Madison, CT?
The summer months are the busiest time in Madison, so booking your vacation rental in advance is essential. You can also find some good deals in the shoulder seasons, like spring and autumn, when the weather is still pleasant but the crowds are smaller.
What are the best rentals for families and kids in Madison, CT?
What events or festivals should visitors check out in and around Madison, CT?
The Madison Beach & Food Festival in July is a popular event, and the annual Madison Arts Festival in September is a great way to experience the local art scene. The nearby town of Guilford also hosts a number of events throughout the year, including the Guilford Fair in August.
What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?
What are the best budget-friendly activities in Madison, CT?
The Madison Green is a great place to relax and enjoy the outdoors, and it's completely free. The Madison Historical Society offers free tours of the historic town hall, and the nearby Hammonasset Beach State Park has free access to the beach and trails.
What are the best restaurants with local dishes in Madison, CT?
For a taste of local seafood, try The Lobster Shack on the waterfront. The Madison Beach Cafe is another popular spot for fresh seafood, and The Griswold Inn is a historic tavern that serves classic New England cuisine.
What are the best walking or cycling routes in Madison, CT?
The scenic coastal path along the shoreline is a great option for walking or cycling. The Hammonasset Beach State Park also has a network of trails for hiking and biking.
Are there pet-friendly attractions in Madison, CT?
Hammonasset Beach State Park is dog-friendly, and the nearby East River Park in Guilford also allows dogs on leash. Many restaurants and shops in Madison are also pet-friendly.
What are the benefits of choosing a vacation rental in Madison, CT?
Vacation rentals offer more space and privacy than hotels, and they often have kitchen facilities, making it easier to cook your own meals. They can also be a more budget-friendly option, especially for larger families or groups.
What are the top sports attractions and facilities in Madison, CT?
Madison is known for its sailing and boating, with the Madison Yacht Club and the Madison Surf Club offering a range of activities. The town also has several parks and recreational facilities, including the Hammonasset Beach State Park, which has a variety of trails for hiking and biking.
Destinations nearby
Best Madison, CT vacation rentals with a balcony
9.6 69 reviews
Madison, CT
22/11 – 29/11
$289/nighttotal: $2023 (7 )
Cozy Garden Apartment Along The Shoreline
1 2
apartment , Guilford
This one-bedroom apartment is located in Guilford, Connecticut, a short drive from New Haven's City Hall and Thimble Islands, offering a peaceful retreat away from the city's bustle. Guests consistently praise the apartment's excellent cleanliness, location, and overall experience. The apartment spans 400 square metres and includes a fully equipped kitchen, a private patio with garden views, and access to a range of amenities including a Jacuzzi, spa, and parking. Enjoy windsurfing and fishing nearby, relax on the terrace, or simply unwind with streaming services and complimentary Wi-Fi.
9.6 16 reviews
Madison, CT
22/11 – 29/11
$759/nighttotal: $5313 (7 )
Charming Cottage By The Sea
2 2
apartment , Guilford
This beach house is situated in Guilford, just 5km from Chaffinch Island State Park, Guilford Art Center, and Hyland House Museum, offering easy access to local attractions. The property has received excellent user ratings, so you can be assured of a comfortable and enjoyable stay. This two-bedroom, two-bathroom property can comfortably accommodate up to six guests. The house provides a range of amenities, including a Jacuzzi, a terrace, a garden, a spa, parking, and a fully equipped kitchen, perfect for relaxing and enjoying your time in Guilford.
Madison, CT
20/06 – 20/08
$9264/nighttotal: $3946464 (426 )
Grace Island. \Nprivate Island! Vacations, Getaways, Weddings & Special Events.
11 2
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 1 review
Madison, CT
23/06 – 26/06
$833/nighttotal: $2499 (3 )
Bliss By The Sea - Cozy Beachside Escape
2 3
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.
Best Madison, CT vacation rentals with parking
10 24 reviews
Madison, CT
23/06 – 26/06
$662/nighttotal: $1986 (3 )
Newly Renovated Beach Cottage!
1 3
apartment , Madison
This Madison cottage, a four-minute walk from a private association beach, is situated in a family-friendly community; the precise distance to Madison landmarks is unspecified. Sleeping six guests, this recently refurbished three-bedroom holiday home boasts a newly renovated kitchen and bathroom, a private breezeway sleeping area, outdoor patio, outdoor shower, and two-car driveway parking.
Madison, CT
22/11 – 29/11
$871/nighttotal: $6097 (7 )
Private Pool! Getaway, 14 Mi To Hammonasset Beach
4 2
house , Killingworth
This Killingworth holiday home, situated approximately 21 kilometres from Wesleyan University and 24 kilometres from the Goodspeed Opera House, offers a peaceful retreat in Connecticut. The 189-square-metre property boasts four bedrooms, two bathrooms, sleeps fifteen guests, and includes a private pool, terrace, free Wi-Fi, and a fully equipped kitchen with dishwasher.
9.9 82 reviews
Madison, CT
22/11 – 29/11
$385/nighttotal: $2695 (7 )
The Rising Tide Cottage
1 2
house , Madison
The Rising Tide Cottage is situated in a peaceful neighbourhood on the Connecticut shoreline, less than 1.6 kilometres from downtown Madison. The cottage boasts excellent ratings for location, cleanliness and user experience. The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, Wi-Fi, and complimentary beach chairs and towels for use at the nearby Pent Road Beach.
Madison, CT
22/11 – 29/11
$620/nighttotal: $4340 (7 )
Coral Cottage - In Clinton Harbor!
3 2
apartment , Clinton
This boutique cottage in Clinton, CT, is a short 300-meter walk from the harbour, boat launch, and waterfront dining establishments including Shanks, Rocky's Aqua, and Lobster Landing, offering convenient access to local attractions such as the Adam Stanton House and General Store Museum. This 139 square meter residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and three provided kayaks for exploring the local waterways.
