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Madison, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Madison, CT

Best Madison, CT vacation rentals with a balcony

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 charming vacation home is located in Guilford, directly across the street from a sandy beach with a playground and within walking distance of the historic Guilford Green. The apartment has received excellent user ratings and is perfect for families and groups seeking a comfortable and convenient stay.
This spacious 4-bedroom, 3-bathroom rental offers 2,700 square feet of living space and comfortably accommodates up to 8 guests. Enjoy a fully equipped kitchen, a wrap-around deck with outdoor dining, a huge backyard, a gas grill, and a variety of outdoor games, plus kayaks, ping pong and foosball tables, beach chairs and an umbrella, and a hot/cold outdoor shower.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
No reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

house, Killingworth
This Killingworth house rental, a peaceful retreat located 13 miles from Wesleyan University and 15 miles from the Goodspeed Opera House, offers easy access to Connecticut attractions.
The 2,030-square-foot home features four bedrooms, two bathrooms, accommodates up to 15 guests, and includes a private pool, Wi-Fi, and a fully equipped kitchen with modern appliances.
Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 32 reviews

Daniel Boone Meets Mid Century Modern Retreat

cabin, Killingworth
This wilderness lodge is located in Killingworth, 20 minutes by car from Mystic Seaport and Mohegan Sun, and adjacent to Chatfield Hollow State Park on 24 acres of private land.
This 2500 sq ft cabin, accommodating up to 10 guests, features 5 bedrooms, 4 bathrooms, a full kitchen, an on-site gym, and outdoor patios with a grill, offering a unique "mid century modern meets Daniel Boone" decor.
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 vacation home is located in Killingworth, a short drive from Hammonasset Beach State Park and Lyman Orchards Golf Course. It has received excellent user ratings, making it a popular choice for travelers.
This 4-bedroom, 2-bathroom rental offers 2,030 square feet of space, comfortably accommodating up to 8 guests. Enjoy a private pool and terrace, a fully equipped kitchen, laundry facilities, and a fireplace.

Guest-Favorite Family Vacation Rentals in Madison, CT

Find the perfect family vacation rental or Airbnb in Madison, CT with plenty of room to spread out near local beaches.

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 vacation home in Killingworth is located near Cockaponset State Forest and Sundial Herb Garden, offering easy access to scenic hiking trails and unique botanical attractions. It has earned excellent user ratings, making it a popular choice for travelers.
This 1300 square foot house comfortably sleeps up to 10 guests in its 4 bedrooms and 1 bathroom. Enjoy the convenience of a fully equipped kitchen, air conditioning, a private terrace, a garden, and parking, perfect for relaxing and exploring the surrounding area.
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 3.5 acres near the Connecticut shoreline (15 minutes away), offers breathtaking views and convenient access to shops and restaurants.
The 4-bedroom, 2-bathroom house sleeps 8, boasts a heated gunite pool and spa (seasonal June-October), a private tennis court, and features a gourmet kitchen, hardwood and slate floors, and two stone fireplaces.
Hollow Brook Estate - Madison, CT
10 3 reviews

Hollow Brook Estate

apartment, Killingworth
This 4-bedroom, 2-bathroom Killingworth vacation rental sits on a secluded 70-acre lakefront estate, offering a private natural setting near the Deacon John Grave House and within reasonable proximity to Madison, CT.
This expansive estate features a pool with a waterfall, private tennis, volleyball, and bocce courts, an outdoor kitchen with a pizza oven, and a separate guest house with a commercial kitchen, game room, and weight room, accommodating up to 12 guests.
Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond - Madison, CT
10 7 reviews

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

house, Killingworth
This luxurious apartment is located in Killingworth, Connecticut, just 15 minutes from shops, restaurants, and the Connecticut shoreline. It is rated excellent by previous guests. This spacious 4-bedroom, 3-bathroom apartment can comfortably accommodate up to 10 guests. It features a private pool, a tennis court, a fully equipped kitchen, and a large garden with a pond.

Frequently Asked Questions about vacation rentals in Madison, CT

  • What are the top family-friendly attractions in Madison, CT?

    The Madison Beach & Recreation Area is a great spot for families, with a playground, picnic areas, and a splash pad. The Hammonasset Beach State Park is another great option, with a large beach, hiking trails, and a nature center.
  • What are the best Airbnb and vacation rentals in Madison, CT?

  • When is the best time to book a vacation rental in Madison, CT?

    The summer months (June to August) are the busiest time for tourism in Madison, so it's best to book your rental well in advance. If you're looking for a more affordable option, you could consider visiting in the shoulder seasons (spring and fall).
  • What are the most popular Airbnbs in Madison, CT?

  • What events or festivals should visitors check out in and around Madison, CT?

    The Madison Beach & Arts Festival in July is a popular event, featuring live music, art exhibits, and food vendors. The Madison Farmers Market takes place every Saturday from May to October, offering local produce and crafts.
  • What are the best vacation rentals with a pool in Madison, CT?

  • What are the best budget-friendly activities in Madison, CT?

    Take a walk or bike ride along the Madison Shoreline Trail, enjoy a picnic at Hammonasset Beach State Park, or explore the Madison Historical Society Museum.
  • What are the best rentals for families and kids in Madison, CT?

  • What are the best restaurants with local dishes in Madison, CT?

    For classic New England seafood, check out The Lobster Landing or The Griswold Inn. The Madison Beach Hotel offers a more upscale dining experience with beautiful views of the Long Island Sound.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

  • What are the best walking or cycling routes in Madison, CT?

    The Madison Shoreline Trail is a great option for a scenic walk or bike ride. It stretches for over 5 miles along the coast, offering views of the Long Island Sound and the surrounding coastline.
  • Are there pet-friendly attractions in Madison, CT?

    Yes, many of Madison's parks and beaches are dog-friendly. Hammonasset Beach State Park has a designated dog beach area, and the Madison Green is also a great spot to walk your furry friend.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison has a number of sports facilities, including the Madison Beach & Recreation Area, which offers a variety of activities like tennis, basketball, and volleyball. The Hammonasset Beach State Park also has a number of hiking trails and a boat launch.

Popular destinations

Best Madison, CT vacation rentals with parking

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 Madison cottage provides convenient access, located an 8-minute walk from Hammonasset Beach State Park and an 11-minute drive from Hammonasset Beach, with nearby attractions including the Allis-Bushnell House and Museum and Scranton Memorial Library. This 450 sq ft rental accommodates two guests with one bedroom and one bathroom, featuring a full kitchen with an ice dispenser, air conditioning, Wi-Fi, an on-site washer and dryer, and garden access.
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 charming waterfront cottage in Madison, Connecticut, offers stunning views of Neck River, Long Island Sound, and Faulkner's Island, just a short distance from the town center. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
The cottage is perfect for families, with a spacious layout accommodating up to 8 guests. It features a fully equipped kitchen, a private beach, a deck with water views, and a variety of amenities for a comfortable stay, including kayaking and paddleboarding.
Relax In A Cabin By The Beach (Cottage No.2) - Madison, CT
9.3 21 reviews

Relax In A Cabin By The Beach (Cottage No.2)

apartment, Madison
This Madison cottage is conveniently located near Madison's beach and greenway trail, a short drive from the downtown area.
The 1-bedroom, 1-bathroom unit sleeps up to 3 guests and features a full kitchen with stove/oven, microwave, and fridge, plus a Smart TV and free Wi-Fi.
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 renovated three-bedroom house in Madison, CT, is located two miles from Hammonasset Beach State Park and a short drive from Bishop's Orchards.
This three-bathroom home sleeps six guests and features a fully equipped kitchen with a Keurig coffee maker, a fireplace, flat-screen TVs, a private yard with a deck, fire pit, and gas grill, plus driveway parking for three cars.

Neighborhoods and points of interest in Madison, CT

Check Out Vacation Rentals with a Pool in Madison, CT

A vacation rental with a pool in Madison, CT is the perfect amenity to complement your time spent by the water.

The Killingworth Estate - Madison, CT
9.8 12 reviews

The Killingworth Estate

house, Killingworth
This 67-acre lakefront estate is located in Killingworth, Connecticut, just a short drive from the charming town center and a scenic distance from the Connecticut shoreline. The property has earned excellent ratings for its location, cleanliness, and overall experience.
The home features four bedrooms and three bathrooms, accommodating up to eleven guests. Enjoy a luxurious stay with private tennis, volleyball, and bocce courts, a pool with a waterfall, an outdoor kitchen with a pizza oven, multiple patios, decks, and gardens.
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 3.5 acres near the Connecticut shoreline (15 minutes away), offers breathtaking views and convenient access to shops and restaurants.
The 4-bedroom, 2-bathroom house sleeps 8, boasts a heated gunite pool and spa (seasonal June-October), a private tennis court, and features a gourmet kitchen, hardwood and slate floors, and two stone fireplaces.
Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond - Madison, CT
10 7 reviews

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

house, Killingworth
This luxurious apartment is located in Killingworth, Connecticut, just 15 minutes from shops, restaurants, and the Connecticut shoreline. It is rated excellent by previous guests. This spacious 4-bedroom, 3-bathroom apartment can comfortably accommodate up to 10 guests. It features a private pool, a tennis court, a fully equipped kitchen, and a large garden with a pond.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
No reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

house, Killingworth
This Killingworth house rental, a peaceful retreat located 13 miles from Wesleyan University and 15 miles from the Goodspeed Opera House, offers easy access to Connecticut attractions.
The 2,030-square-foot home features four bedrooms, two bathrooms, accommodates up to 15 guests, and includes a private pool, Wi-Fi, and a fully equipped kitchen with modern appliances.

Discover Vacation Rentals by the Sea in Madison, CT

Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Madison, CT. Book your next shoreside stay today.

Charming Madison, Ct Carriage House Ocean Rental - Madison, CT
10 39 reviews

Charming Madison, Ct Carriage House Ocean Rental

apartment
Spacious Family Beach House - Madison, CT
10 3 reviews

Spacious Family Beach House

apartment, Madison
One Bedroom Apt-cristys Madison - Madison, CT
9.8 19 reviews

One Bedroom Apt-cristys Madison

apartment, Madison
Waterfront Apartment-guilford Ct-***new Listing - Madison, CT
10 85 reviews

Waterfront Apartment-guilford Ct-***new Listing

apartment, Guilford

Discover 5-Star Vacation Rentals in Madison, CT

Refined interiors and prime locations make these luxury waterfront vacation rentals in Madison, CT the ideal choice for your stay.

2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.8 11 reviews

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

apartment, Madison

Best Vacation Rentals with a Steam Room in Madison, CT

Maximize your recovery with an on-site sauna, a standard feature at these premier Madison, CT vacation rentals.

Stylish Modern Tiny Stay Steps From The Ocean - Madison, CT
9.3 17 reviews

Stylish Modern Tiny Stay Steps From The Ocean

house, Clinton
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