Compare Vacation Rentals & Airbnb in Madison, CT

156 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Madison, CT vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

156 Rentals and Airbnb in Madison, CT

Best family friendly Madison, CT vacation rentals

Among the 156 accommodations in Madison, CT, here are the 4 best family friendly rentals

Perfect Cape Beach Cottage In Madison Ct! - Madison, CT
9.7 42 reviews

Perfect Cape Beach Cottage In Madison Ct!

apartment, Madison
This Madison, Connecticut beach cottage offers deeded access to a private sandy beach, located steps from the shore in a quiet neighbourhood.
The two-bedroom, two-bathroom property sleeps six, features a full kitchen with freezer and dishwasher, a private backyard, patio, wraparound deck, and air conditioning; note that bedrooms are upstairs via a spiral staircase.
Coastal Farmhouse Walking Distance To Town - Madison, CT
10 68 reviews

Coastal Farmhouse Walking Distance To Town

apartment, Guilford
This fully renovated apartment is located a short walk (1.1 miles) from Guilford's historic town green, which is filled with restaurants and shops. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms, two bathrooms, and can comfortably accommodate up to six guests. It features air conditioning, a fully equipped kitchen, and easy access to nearby beaches, shopping, and the town's attractions.
Charm + Location. Walk To Beach, Town, & Harbor. - Madison, CT
9.9 302 reviews

Charm + Location. Walk To Beach, Town, & Harbor.

apartment, Guilford
This charming cottage is ideally situated in Guilford, within easy walking distance of the town's main attractions, including the green, the harbour, and the beach. It boasts excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage offers two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy its well-equipped kitchen, spacious living areas, screened porch, large side yard, and bike rentals, perfect for exploring the area.
Cheerful 4br Home-7 Min Walk To Private Beach - Madison, CT
9.8 21 reviews

Cheerful 4br Home-7 Min Walk To Private Beach

house, Madison
This four-bedroom, three-bathroom apartment in Kelsey Place, Madison, offers easy access to a private beach, the precise distance requiring further clarification regarding Kelsey Place's location relative to Madison landmarks.
Sleeping up to ten guests, the property features a spacious layout including a master suite with private balcony and a ground floor bedroom with en-suite bathroom, boasting modern amenities such as a dishwasher and air conditioning, alongside a garden and parking.

Best Madison, CT vacation rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 2 best rentals with a pool

The Killingworth Estate - Madison, CT
9.8 12 reviews

The Killingworth Estate

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.
Luxury Riverfront Estate | Pool, Spa & Tennis - Madison, CT
10 46 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.

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 most popular Airbnbs in Madison, CT?

  • 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.

Popular destinations

Best Madison, CT vacation rentals with a balcony

Lakehouse W/ Hot Tub In Clinton, Ct - Madison, CT
10 1 review

Lakehouse W/ Hot Tub In Clinton, Ct

apartment, Clinton
This lakefront property in Clinton offers scenic water views and direct access to a beach-style lake entry just 60 metres away, set within a wooded, nature-filled location.
This four-bedroom flat accommodates up to ten guests, featuring a two-level layout, a hot tub, an indoor fireplace, and a private deck perfect for observing local wildlife.

Best Madison, CT vacation rentals with parking

Modern Hammonassett River Retreat - Madison, CT
9.9 37 reviews

Modern Hammonassett River Retreat

cabin, Clinton
This renovated cabin is located on a picturesque knoll with direct river access, just 5 kilometres from Hammonasset State Park and Madison Town Center. It has received excellent ratings for location, cleanliness, and overall user experience.
The lodge offers 3 bedrooms and 2 bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a hot tub, an outdoor kitchen and shower, a fire pit, and a spacious deck overlooking the river.
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.
Cozy Beach Cottage Close To Everthing - Madison, CT
9.8 58 reviews

Cozy Beach Cottage Close To Everthing

apartment, Madison
This Madison cottage, situated 1.6 km from restaurants and shops, offers stunning water views from the family room and bedrooms.
Sleeping four guests, this two-bedroom, two-bathroom holiday home boasts a fully equipped kitchen, air conditioning, garden, parking, and a fire pit; nearby swimming and cycling opportunities further enhance its appeal.
Charming 3 Bedroom Home Minutes From Beach - Madison, CT
10 7 reviews

Charming 3 Bedroom Home Minutes From Beach

apartment, Madison
This recently renovated barn-style dwelling offers a unique country and beach escape, located just minutes from Madison town centre and the Madison beaches, with Hammonasset State Park a short drive away.
This spacious 3-bedroom, 2-bathroom flat accommodates up to 6 guests and features a kitchen with a fridge, air conditioning, and a garden, whilst the development boasts a fitness centre and parking.
©2026 cozycozy.com