Holiday Rentals in Madison, CT

156 available vacation rental offers

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

Best Holiday rentals and Airbnb offers in Madison, CT

Best family friendly Madison, CT holiday rentals

Among the 156 accommodations in Madison, CT, here are the 1 best family friendly rentals

Historic New England Home ,Reunions Beach Pass - Madison, CT
9.2 90 reviews

Historic New England Home ,Reunions Beach Pass

apartment, Guilford
This four-bedroom house is located in Guilford, within a 15-minute walk of the Guilford Art Center and Hyland House Museum, and less than 2km from the Henry Whitfield State Museum and Bishops Orchard and Winery. It has received excellent ratings from previous guests.
The property spans 186 square metres and can comfortably accommodate up to six guests. It features a garden, barbecue grills, a fully equipped kitchen, free Wi-Fi, a fireplace, and a terrace, perfect for enjoying the outdoors and relaxing after exploring the local area.

Best Madison, CT holiday rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 1 best rentals with a pool

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.

Frequently asked questions about holiday rentals in Madison, CT

Popular destinations

Best Madison, CT holiday rentals with a balcony

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.
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.
Welcoming Tiny Home! Downtown & Beachy️ - Madison, CT
10 24 reviews

Welcoming Tiny Home! Downtown & Beachy️

apartment, Guilford
Seagrass Bungalow is a charming mini-home located in the centre of Guilford, just a short walk from the town green, shops, restaurants, and Jacobs Beach. This highly rated property has received excellent reviews from previous guests.
The self-catering bungalow can accommodate up to two guests and is perfect for a romantic getaway. Enjoy the private deck, outdoor shower, fire pit, and large grassy yard, or relax in the spa and take advantage of the on-site parking.
Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck. - Madison, CT
10 63 reviews

Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck.

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 holiday rentals with parking

2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.5 2 reviews

2 Mi To Dtwn: 2-acre Retreat W/ Large Yard!

house, Madison
This three-bedroom house, perfect for eleven guests, is situated in Madison, Connecticut, a two-mile (3.2km) drive from the town centre and within walking distance of Hammonasset Beach State Park.
The 372-square-metre property boasts a fully equipped kitchen, three bathrooms, free Wi-Fi, and parking, with proximity to New Haven's attractions including Yale University and Tweed-New Haven Airport.
Walk To Coast! Convenient Cottage In Dtwn Madison - Madison, CT
8.0 1 review

Walk To Coast! Convenient Cottage In Dtwn Madison

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.
New Coastal Cottage 2 Miles To Beach + Lake Access - Madison, CT
10 8 reviews

New Coastal Cottage 2 Miles To Beach + Lake Access

apartment, Clinton
This holiday let in Clinton is located 3.2 kilometres from Hammonassett Beach and a short walk to Boulder Lake Beach, with downtown Madison and Clinton also 3.2 kilometres away.
This two-bedroom bungalow accommodates up to six guests and features air conditioning, Wi-Fi, a microwave oven, a dishwasher, and a screened-in porch with an outdoor picnic table and fire pit.
New Charming Coastal Bungalow Steps From The Beach - Madison, CT
10 1 review

New Charming Coastal Bungalow Steps From The Beach

house, Madison
This coastal bungalow in Madison offers unparalleled proximity, situated just a 1-minute walk from Hammonasset Beach, with Thimble Islands 26 kilometres and Goodspeed Opera House 32 kilometres away.
This 70 square metre accommodation features one bedroom and one bathroom, a fully equipped kitchen, free Wi-Fi, and private parking, accommodating up to 11 guests, and is managed by a private host for a personalised experience.
©2026 cozycozy.com