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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

Iconic Beachfront Summer Estate East, Shared Pool - Madison, CT
9.8 55 reviews

Iconic Beachfront Summer Estate East, Shared Pool

apartment
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.
Clinton Beach House & Cottage W/ Pool, Near Shore - Madison, CT
9.9 23 reviews

Clinton Beach House & Cottage W/ Pool, Near Shore

apartment, Clinton
This five-bedroom, three-bathroom house in Clinton is located a short distance (approximately 0.24 km) from the town's marinas and beach.
Sleeping up to 14 guests, this spacious property boasts a private in-ground pool, fully fenced backyard with fire pit, and is close to Clinton's waterside attractions.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
9.0 6 reviews

Stunning Historic Waterfront Mansion With Pool

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.
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.

Best family friendly Madison, CT lodging

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

Coastal Getaway On Marsh Near Beach, Town, Trails - Madison, CT
9.9 14 reviews

Coastal Getaway On Marsh Near Beach, Town, Trails

apartment, Guilford
This three-bedroom Guilford property, a short 1.6km drive from Guilford Green, offers easy access to Hammonasset Beach and Thimble Island Cruises.
The spacious house, featuring a remodeled kitchen, two bathrooms, and a two-car garage, comfortably accommodates eight guests and includes amenities such as beach equipment, a barbecue, and ample bedding.
Summer Is Filling Up-beach, Shopping And Golf - Madison, CT
9.8 6 reviews

Summer Is Filling Up-beach, Shopping And Golf

apartment, Clinton
This seaside Clinton holiday home is situated within 3.2km of Bailey's Dog Park and Clinton Crossing Premium Outlets, and within 4.8km of Clinton Plaza Shopping Centre and the Adam Stanton House and General Store Museum.
This three-bedroom, three-bathroom property offers 177 square metres of space, accommodating up to six guests, and features a fully equipped kitchen, garden, terrace, free Wi-Fi, on-site arcade, and barbecue facilities.
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.
Quiet Killingworth Rental W/ Deck & Grill! - Madison, CT
10 16 reviews

Quiet Killingworth Rental W/ Deck & Grill!

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.

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

Seaside Sanctuary Steps From Long Island Sound - Madison, CT
10 2 reviews

Seaside Sanctuary Steps From Long Island Sound

apartment, Westbrook
This Westbrook Centre holiday home, a block from Route 1 and five minutes from Route 95, offers easy access to Westbrook's downtown area, marina, and local restaurants.
The 260 square metre (2800 square feet) property boasts four bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, outdoor shower, ample parking, and proximity to the Katharine Hepburn Cultural Arts Center and Mashantucket Pequot Museum & Research Centre.
Coastal Getaway With Water Views In Every Room - Madison, CT
10 10 reviews

Coastal Getaway With Water Views In Every Room

apartment, Madison
This beachfront property in Madison, Connecticut, approximately 16km from Guilford, offers spectacular views of the Long Island Sound and is close to attractions such as the Deacon John Grave House and Scranton Memorial Library.
Sleeping six comfortably, this three-bedroom, one-bathroom apartment provides a fridge, dishwasher, air conditioning, parking, internet access, and is pet-friendly, ideal for families visiting the Guilford area.
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.
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.

Best Madison, CT accommodations with a kitchen

Waterfront Lakehouse Getaway In Clinton W/ Hot Tub - Madison, CT
8.6 26 reviews

Waterfront Lakehouse Getaway In Clinton W/ Hot Tub

apartment, Clinton
The Lakehouse retreat is situated on the tranquil shores of a lake in Clinton, just a short drive from the town centre and a few minutes from the scenic Clinton River Trail. This lakeside retreat offers a peaceful escape from the hustle and bustle of city life.
The Lakehouse comfortably accommodates up to ten guests in four bedrooms, making it ideal for families or groups of friends. The property features a private dock, a cosy fireplace, a garden, and a fully equipped kitchen with a fridge and microwave.
Private Lake Hideaway Nestled In The Woods - Madison, CT
8.9 13 reviews

Private Lake Hideaway Nestled In The Woods

apartment, Deep River
This four-bedroom property is located in Deep River, just a short distance from the town centre and its attractions, surrounded by private woodland and bordering state forests. The accommodation has received excellent user, location and cleanliness ratings.
The property has three bathrooms and can comfortably accommodate up to eight guests. It offers a private solarium, a deck, a master suite with panoramic views, exclusive lakefront access, and a tranquil and secluded setting.
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 Rising Tide Cottage - Madison, CT
9.9 95 reviews

The Rising Tide Cottage

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.
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