Find short term rentals in Madison, CT at the best prices

146 available short term rental offers

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Madison, CT short term rentals
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Best Short term and Weekly rentals in Madison, CT

Best family friendly Madison, CT Short term rentals

Among the 146 accommodations in Madison, CT, here are the 4 best family friendly rentals

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.
Hollow Brook Estate - Madison, CT
10 3 reviews

Hollow Brook Estate

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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 77 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.
Charming Madison, Ct Carriage House Ocean Rental - Madison, CT
10 39 reviews

Charming Madison, Ct Carriage House Ocean Rental

apartment
This charming cottage is located just a few hundred metres from the beach and a short walk from Madison's town centre, offering a peaceful retreat close to the action. It consistently receives excellent reviews for its location, cleanliness, and overall experience.
The cottage comfortably sleeps four guests and features a well-equipped kitchen, a private garden, and parking for one car. Guests can enjoy air conditioning, modern amenities, and a sunny porch for relaxing and soaking up the fresh air.

Best Madison, CT lodging with a balcony

Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 32 reviews

Daniel Boone Meets Mid Century Modern Retreat

cabin, Killingworth
This expansive five-bedroom lodge in Killingworth, Connecticut, offers 232 square meters of living space and is conveniently located near Chatfield Hollow State Park, Chamard Vineyards, and a short drive from Clinton Crossing Premium Outlets.
Guests can enjoy a mid-century modern sanctuary with a fully equipped kitchen, an on-site gym, and outdoor patios with a grill, perfect for exploring the surrounding 24 acres or visiting nearby attractions such as the Ivoryton Playhouse and Mystic Seaport, with year-round outdoor activities like hiking and apple picking readily available.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.6 13 reviews

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger

apartment, Haddam
This waterfront property is located in Killingworth, Connecticut, just a short distance from Cockaponset State Forest and Sundial Herb Garden, offering easy access to nature and local attractions. The property has received excellent guest ratings, highlighting its comfortable and enjoyable stay.
This four-bedroom house spans 121 square metres and comfortably accommodates up to 10 guests. It features a fully equipped kitchen, a terrace, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.
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.
Scranton Seahorse Inn - Madison, CT
9.1 292 reviews

Scranton Seahorse Inn

B&B, Madison
The Scranton Seahorse Inn is situated in Madison, Connecticut, just a short drive from Hammonasset Beach State Park and Madison Country Club. It consistently receives excellent ratings for location, cleanliness, and overall user experience.
The inn offers a comfortable and welcoming stay with a single bedroom and bathroom. Guests can enjoy a range of amenities and activities, including a jacuzzi, terrace, garden, spa, concierge service, fitness centre, room service, and complimentary bicycle rentals.

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Best Madison, CT lodging with a kitchen

Walk To Coast! Convenient Cottage In Dtwn Madison - Madison, CT
9.0 2 reviews

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.
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.7 21 reviews

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

apartment, Madison
This Madison, Connecticut holiday home is situated 3.2km from Hammonasset Beach State Park and offers easy access to Bishop's Orchards and Madison's town centre.
The three-bedroom, three-bathroom property sleeps six, boasting a fully equipped kitchen with modern appliances, a private garden with fire pit and gas grill, driveway parking for three cars, and features a blend of period details and contemporary comforts.
New Coastal Cottage 2 Miles To Beach + Lake Access - Madison, CT
10 9 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.
Walk To Coast! Convenient Cottage In Dtwn Madison - Madison, CT
10 5 reviews

Walk To Coast! Convenient Cottage In Dtwn Madison

apartment, Madison
This studio apartment in Madison is located behind a well-regarded French restaurant, offering a walkable neighbourhood with easy access to local attractions.
This self-contained unit accommodates up to four guests with a queen bed and a queen sleeper sofa, featuring a private balcony, a Smart TV, reserved parking, and a Pack 'n Play for families.

Best Madison, CT lodging with laundry available

Coastal Getaway With Water Views In Every Room - Madison, CT
9.8 68 reviews

Coastal Getaway With Water Views In Every Room

apartment, Madison
This three-bedroom Madison waterfront apartment, boasting stunning views of the Long Island Sound and East River, offers convenient access to local attractions.
Sleeping up to six guests, the property features a modern open-plan layout, including a private deck, two parking spaces, and a fully equipped kitchen with dishwasher, plus a private garage and internal stairs.
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.
Newly Renovated Carriage House Near Town & Beaches - Madison, CT
10 6 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.
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly! - Madison, CT
10 1 review

Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!

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.
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