Holiday Rentals in Madison, CT

156 available vacation rental offers

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Madison, CT holiday rentals
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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 2 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.
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.

Best Madison, CT holiday rentals with a pool

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

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.

Frequently asked questions about holiday rentals in Madison, CT

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Best Madison, CT holiday rentals with a balcony

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.
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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 76 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.
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.

Best Madison, CT holiday rentals with parking

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.
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.
Welcoming 1-bedroom Cottage In Charming Madison Is One Mile To Town And Beach! - Madison, CT
10 1 review

Welcoming 1-bedroom Cottage In Charming Madison Is One Mile To Town And Beach!

cottage, Madison
This one-bedroom bungalow in Madison is located an 8-minute walk from Hammonasset Beach State Park and a short drive from Hammonasset Beach, with convenient access to cultural sites such as the Allis-Bushnell House and Museum and the Hyland House Museum.
The 42 square metre property accommodates two guests and features a fully equipped kitchen, complimentary Wi-Fi, air conditioning, an on-site garden, and off-street parking, with an in-unit washer and dryer provided for added convenience.
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