Compare vacation rentals in Madison, CT from 100+ sites!

156 available vacation rental offers

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

Best Vacation rentals and Airbnb offers in Madison, CT

Best Madison, CT vacation rentals with a balcony

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.
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.
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
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.

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 boasts deeded access to a private sandy beach, located steps from the shoreline in a quiet neighborhood.
The two-bedroom, two-bathroom rental sleeps six guests and features a full kitchen, private backyard with patio and wraparound deck, and modern interior design.
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 four houses from the water in Madison, Connecticut, within easy walking distance of three town beaches, the Madison Beach Club, and the town center. Guest reviews consistently praise the cottage's excellent location, cleanliness, and overall experience.
The cottage features a private carriage house with all-new furniture, a sunny porch, and one car parking. Enjoy a comfortable stay with amenities like air conditioning, a fully equipped kitchen, and a queen sleeper in the family room, perfect for a getaway with up to four 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.
Coastal Farmhouse Walking Distance To Town - Madison, CT
10 68 reviews

Coastal Farmhouse Walking Distance To Town

apartment, Guilford
This Guilford apartment is conveniently located near the town green, a short walk from restaurants and shops, with scenic salt marsh views. The apartment has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. This three-bedroom, two-bathroom apartment comfortably sleeps six guests. Enjoy modern amenities, air conditioning, and a fully equipped kitchen, ideal for preparing meals.
The apartment is close to beaches like Jacob's Beach and Madison Surf Club Beach, as well as shopping outlets like Clinton Crossings. Enjoy a peaceful retreat while still being close to the town's attractions.

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

Charming Cottage Is 1 Mile From Town And Beach - Madison, CT
9.8 13 reviews

Charming Cottage Is 1 Mile From Town And Beach

house, Madison
This renovated 1-bedroom, 1-bathroom cottage is located in a quiet residential area just 1 mile from downtown Madison and its beaches, offering a 10-minute walk to the village.
This furnished cottage accommodates up to 2 guests with an open-concept living area, a kitchen equipped with a fridge, microwave, and dishwasher, and air conditioning, providing easy access to shoreline activities.
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.
Charming 3 Bedroom Home Minutes From Beach - Madison, CT
10 7 reviews

Charming 3 Bedroom Home Minutes From Beach

apartment, Madison
This renovated barn-style house is located a short drive from Madison's town center, Madison beaches, and Hammonasset State Park, offering a unique blend of country and beach ambiance.
This 3-bedroom, 2-bathroom dwelling accommodates up to 6 guests and features a kitchen with a fridge, air conditioning, internet, a garden, fitness center, and 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 a prime location just a 1-minute walk from Hammonasset Beach, with Thimble Islands 16 miles away and Tweed-New Haven Airport 19 miles away.
This 750 square foot cottage accommodates up to 11 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen, free WiFi, and private parking.

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.

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.
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.
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.

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.

New Charming Coastal Bungalow Steps From The Beach - Madison, CT
10 12 reviews

New Charming Coastal Bungalow Steps From The Beach

apartment, Madison
Beach Sanctuary On The Long Island Sound - Madison, CT
9.9 61 reviews

Beach Sanctuary On The Long Island Sound

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.

Beautifully Furnished Apartment - Madison, CT
9.7 103 reviews

Beautifully Furnished Apartment

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.

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
©2026 cozycozy.com