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Madison, CT place to stay
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179 Lodgings in Madison, CT

Best Madison, CT lodging with a pool

Among the 179 accommodations in Madison, CT, here are the 4 best ones with a pool

Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 11 reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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.
Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond - Madison, CT
10 7 reviews

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

house, Killingworth
This luxurious four-bedroom apartment is situated in Killingworth, Connecticut, just 15 kilometres from shops, restaurants, and the Connecticut shoreline. It is rated excellent by previous guests and offers a peaceful retreat in a secluded natural setting.
The property spans 334 square metres and comfortably accommodates up to 10 guests. Enjoy a range of amenities, including a heated swimming pool, a Jacuzzi, a private tennis court, and a fully equipped kitchen with top-of-the-line appliances.
Luxury Riverfront Estate | Pool, Spa & Tennis - Madison, CT
10 39 reviews

Luxury Riverfront Estate | Pool, Spa & Tennis

house, Killingworth
This luxurious Killingworth estate, situated on a secluded 3.5-acre property approximately 24km from the Connecticut shoreline, offers breathtaking views and complete privacy.
The four-bedroom, two-bathroom dwelling boasts a heated swimming pool and spa (seasonal June-October), a private tennis court, and ample space for eight guests, including a gourmet kitchen with top-of-the-line appliances and a vintage dining room table seating up to ten.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
No reviews

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.

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.

Best family friendly Madison, CT lodging

Among the 179 accommodations in Madison, CT, here are the 4 best for families

Marina Chic: Bright Seaside Gem - Madison, CT
10 37 reviews

Marina Chic: Bright Seaside Gem

apartment, Guilford
The Point House in Guilford, Connecticut offers a superb location, a short walk from Guilford's beaches, restaurants, a marina, and the Guilford train station.
This three-bedroom, three-bathroom holiday home sleeps six (with an additional blow-up bed available), boasting a modern interior, full kitchen with dishwasher, air conditioning, a jacuzzi, and ample parking.
Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included - Madison, CT
10 1 review

Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included

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.
Scenic Mulberry Point Connecticut Beach House - Madison, CT
9.9 83 reviews

Scenic Mulberry Point Connecticut Beach House

apartment, Guilford
This beachfront property is located in Guilford, just a short distance from Daniel's Beach, overlooking Indian Cove and Faulkners Lighthouse, offering stunning views of the coastline. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a spacious living area, and a private garden with a barbecue and fire pit, perfect for enjoying the outdoors. Guests can also enjoy the sunroom and deck, offering stunning views of the ocean.
Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 5 reviews

Newly Renovated Carriage House Near Town & Beaches

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.

Frequently asked questions about accommodations in Madison, CT

  • What are the most convenient modes of transportation within Madison, CT?

    Madison is a relatively small town, so getting around is easy. You can easily walk or bike around the town centre and the beach areas. If you're planning to explore further afield, renting a car is the best option. There is also a local bus service, but it's not as frequent as in larger cities.
  • What outdoor activities and adventures are popular in and around Madison, CT?

    Madison is a haven for outdoor enthusiasts. The town has several parks and nature preserves, perfect for hiking, kayaking, and birdwatching. The Hammonasset Beach State Park offers opportunities for swimming, sunbathing, and fishing. For a more challenging adventure, try rock climbing at East Rock Park in nearby New Haven.
  • What types of accommodations are available in Madison, CT?

    Madison offers a range of accommodation options to suit all budgets. You can find charming bed and breakfasts, comfortable motels, and luxurious hotels. There are also several vacation rentals available, from cosy cottages to spacious apartments. For a unique experience, consider staying at the Madison Beach Hotel, a historic landmark with stunning ocean views.
  • When is the best time to visit Madison, CT?

    The best time to visit Madison is during the summer months, from June to August, when the weather is warm and sunny, and the beaches are bustling with activity. If you prefer a quieter experience, spring and autumn offer pleasant weather and fewer crowds. You can also enjoy the festive atmosphere of the holiday season in December.
  • What local dishes and culinary experiences are a must-try in Madison, CT?

    Madison has a vibrant culinary scene, with a focus on fresh seafood and local produce. Be sure to try the lobster rolls, a classic New England dish. The town is also home to several excellent Italian restaurants, serving up delicious pasta and pizza. For a sweet treat, try the famous Madison Beach Hotel's ice cream, a local favourite.
  • In which part of Madison, CT should you consider renting accommodation?

    The best areas to rent accommodation in Madison depend on your preferences. If you want to be close to the beach, consider staying in the Madison Beach area. For a more central location, the historic town centre offers easy access to shops, restaurants, and attractions. If you prefer a quieter setting, the residential areas of the town are also a good option.

Popular destinations

Best Madison, CT accommodations with a balcony

Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
No reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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.
The Millhouse Downtown Chester - Madison, CT
10 120 reviews

The Millhouse Downtown Chester

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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 72 reviews

New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026

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.

Best Madison, CT accommodations with a kitchen

Rosemary Lane House | Walk To Guilford Green - Madison, CT
9.4 127 reviews

Rosemary Lane House | Walk To Guilford Green

apartment, Guilford
This apartment is situated in a peaceful neighbourhood just off the south side of the Guilford Green, within a 1km walk of the town centre, restaurants, and the train station. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The three-bedroom property can comfortably accommodate up to eight guests. It features a modern kitchen with a fridge, freezer, microwave, and dishwasher, a private garden, parking, air conditioning, a washer and dryer, and a finished walk-out basement with a ping pong table and TV.
Beach With Free Pass! Shopping Outlets And Golf! - Madison, CT
9.6 84 reviews

Beach With Free Pass! Shopping Outlets And Golf!

apartment, Clinton
This apartment is located in Madison, Connecticut, just a short drive from Clinton, with easy access to 15 miles of beach, downtown Madison, and premium outlets within 8 kilometres. The property has excellent user, location and cleanliness ratings, making it a highly recommended choice for travellers.
The apartment offers comfortable accommodation for up to 6 guests with multiple bedrooms, a game room and a sunroom with a deck. It comes with a fully equipped kitchen, air conditioning, a private garden, parking and internet access, providing everything you need for a relaxing and enjoyable stay.
Madison Riverside Retreat - Madison, CT
9.9 14 reviews

Madison Riverside Retreat

apartment, Madison
This riverside house in Madison, Connecticut, is situated 8km from Madison's shoreline, beaches, and downtown area, offering easy access to shops and restaurants.
Sleeping up to five guests, this three-bedroom, two-bathroom property boasts a chef's kitchen, extensive outdoor decking with a fire pit overlooking the Hammonasset River, and a fitness centre; nearby activities include biking, hiking, fishing, and paddling.
The Millhouse Downtown Chester - Madison, CT
9.8 25 reviews

The Millhouse Downtown Chester

apartment, Chester
This apartment is located in Chester Center, just 0.5km from the Norma Terris Theater and within 5km of several attractions including Connecticut Valley Railroad State Park Trail, Connecticut River, Chester Creek Marina, and Gillette Castle State Park. It has received excellent user ratings.
This two-bedroom, two-bathroom apartment is 93 square meters and can accommodate up to 5 guests. It offers a fully equipped kitchen, free WiFi, a terrace, a garden, a spa, parking, and access to barbecue grills.
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