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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 59 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.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
No reviews

Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.

houseboat, Clinton
This houseboat in Clinton, CT, is docked at a prime location, offering easy access to RJ Julia Booksellers and Clinton Crossing Premium Outlets, just a short distance away.
This four-bedroom, four-bathroom yacht accommodates up to eight guests, featuring a king bed, queen bed, and two twin beds, along with a flybridge bar and an aft deck dining area perfect for entertaining.
Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 27 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 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included - Madison, CT
10 1 review

Private 2nd-floor Apt | 4 Mins To Beach | Ev Charger & Parking Included

apartment, Westbrook
This 1-bedroom, 1-bathroom apartment in Westbrook Center is located 4 minutes from West Beach and less than 1 mile (approximately 5,280 feet) from Westbrook Outlets, offering central access to Route 1 for day trips and proximity to attractions like the Connecticut Valley Railroad State Park. This 540 square foot dwelling accommodates up to 4 guests with air conditioning, a full kitchen including a dishwasher, and off-street parking with a Level 2 EV charger.

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.

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

Historic New England Home ,Reunions Beach Pass

apartment, Guilford
This Guilford vacation home is located within walking distance of the Guilford Art Center, Hyland House Museum, and Bishops Orchard and Winery, offering easy access to local attractions. Guests consistently rate this property as excellent, making it a popular choice for travelers.
This 4-bedroom home provides ample space for families or groups of up to 6 guests, with a spacious 2000 square feet of living area. The house includes a fully equipped kitchen, a fireplace, a garden, and a terrace, perfect for enjoying meals, relaxing, and exploring the area.
Coastal Getaway On Marsh Near Beach, Town, Trails - Madison, CT
9.8 13 reviews

Coastal Getaway On Marsh Near Beach, Town, Trails

apartment, Guilford
This three-bedroom, two-bathroom Guilford vacation rental is located on a quiet cul-de-sac, one mile from Guilford Green and a short drive from Hammonasset Beach State Park and the train station.
The 3+ bedroom home features an open floor plan, sleeps eight guests, includes a fenced yard, two-car garage, and amenities such as Wi-Fi, air conditioning, and a grill; enjoy birdwatching from the deck overlooking the marsh.
Charming Cottage By The Sea - Madison, CT
9.6 17 reviews

Charming Cottage By The Sea

apartment, Guilford
This beachfront vacation rental in Guilford is conveniently located within a 3-mile radius of popular attractions like Chaffinch Island State Park, Guilford Art Center, and Bishops Orchard and Winery. Guests have consistently rated this property as excellent, making it a top choice for travelers seeking a comfortable and enjoyable stay.
The home features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy a relaxing stay with amenities like a Jacuzzi, a fireplace, a terrace, and a fully equipped kitchen.
Shabby Chic Retreat - Madison, CT
10 111 reviews

Shabby Chic Retreat

apartment, Madison
Greenfield Cottage is located in a peaceful neighborhood, just a short drive from Hammonasset State Park & Beach and Chatfield Hollow. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience.
This studio apartment is ideal for families or small groups, comfortably accommodating up to 4 guests. Enjoy amenities like a fully equipped kitchen, a private garden, and a soundproofed studio with a separate entrance, making it perfect for a relaxing and enjoyable stay.

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

42 Wall - The Heart Of Madison - Madison, CT
9.8 19 reviews

42 Wall - The Heart Of Madison

apartment, Madison
This 2-bedroom, 1-bathroom condo offers an excellent downtown Madison location on Wall Street, providing immediate walking access to shops, restaurants, the library, movie theater, the beach, town green, and the shoreline.
This apartment accommodates up to 4 guests and features air conditioning, a kitchen with a fridge, freezer, microwave, and dishwasher, making it a convenient base for exploring Madison.
New Charming Coastal Bungalow Steps From The Beach - Madison, CT
10 10 reviews

New Charming Coastal Bungalow Steps From The Beach

apartment, Madison
This 2-bedroom condo in Madison is located in a walkable coastal area, just 500 feet from the beach and 1.5 miles from downtown.
This recently remodeled 750 sq ft apartment accommodates up to 6 guests with 2 queen beds and a pull-out couch, featuring a full kitchen, air conditioning, internet, and parking for 2 vehicles, and is minutes from Hammonasset Beach State Park.
Charming Cottage Is 1 Mile From Town And Beach - Madison, CT
10 5 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.
The Davis House - Madison, CT
9.8 68 reviews

The Davis House

apartment, Guilford
This 3-bedroom, 3-bathroom apartment is located in a peaceful neighborhood in Guilford, just a mile from the historic town green and a half mile from Interstate 95. This rental consistently receives excellent ratings for its cleanliness, location, and overall experience.
The apartment offers a spacious layout with a large fenced-in yard, perfect for relaxing or entertaining. Guests can enjoy a fully equipped kitchen, air conditioning, and access to outdoor activities like hiking, biking, and kayaking, all within a short drive.

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.

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.
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.
Luxury Riverfront Estate | Pool, Spa & Tennis - Madison, CT
10 39 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.

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.

Beachfront Cottage With Panoramic Views Of Long Island Sound In Madison Ct - Madison, CT
10 8 reviews

Beachfront Cottage With Panoramic Views Of Long Island Sound In Madison Ct

cottage, Madison
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 72 reviews

New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026

apartment, Madison
Spacious Family Beach House - Madison, CT
10 2 reviews

Spacious Family Beach House

apartment, Madison
Entire Home - Cheerful 4 Bedroom On The Shoreline. - Madison, CT
10 39 reviews

Entire Home - Cheerful 4 Bedroom On The Shoreline.

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.

The Rising Tide Cottage - Madison, CT
9.9 85 reviews

The Rising Tide Cottage

house, 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.

Guilford Oceanfront - Walk To Beach, Green, Train - Madison, CT
10 2 reviews

Guilford Oceanfront - Walk To Beach, Green, Train

apartment, Guilford
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