Compare Vacation Rentals & Airbnb in Madison, CT

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Madison, CT vacation rentals
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105 Rentals and Airbnb in Madison, CT

Best family friendly Madison, CT vacation rentals

Among the 105 accommodations in Madison, CT, here are the 4 best family friendly rentals

Edwin Leete House - Madison, CT
10 41 reviews
Madison, CT
11/12 – 12/12
$1529/nightfor 1 night

Edwin Leete House

2 6
apartment , Guilford
The Carriage House is situated in Guilford's historic district, just a block from the Guilford Green and a short walk to the beach and marina. This charming property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom house can comfortably accommodate up to seven guests. The Carriage House offers a fully equipped kitchen, a private garden, parking, and air conditioning, ensuring a comfortable and enjoyable stay.
Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt - Madison, CT
8.8 23 reviews
Madison, CT
02/08 – 07/08
$406/nighttotal: $2030 (5 )

Walk To Goodspeed Opera House From This Quaint 2 Bdrm Apt

2 4
apartment , East Haddam
This East Haddam apartment is ideally located a two-minute walk from the Goodspeed Opera House, 27 kilometres from Wesleyan University, and 45 kilometres from Eastern Connecticut State University.
This two-bedroom, one-bathroom flat offers 84 square metres of space, sleeping up to nine guests and boasting a fully equipped kitchen, air conditioning, free on-site parking, and a private entrance.
The Millhouse Downtown Chester - Madison, CT
9.8 23 reviews
Madison, CT
02/08 – 07/08
$776/nighttotal: $3880 (5 )

The Millhouse Downtown Chester

3 4
apartment , Chester
This apartment is located in Chester Center, just 0.5km from the Norma Terris Theater and within 5km of several attractions including Connecticut Valley Railroad State Park Trail, Connecticut River, Chester Creek Marina, and Gillette Castle State Park. It has received excellent user ratings.
This two-bedroom, two-bathroom apartment is 93 square meters and can accommodate up to 5 guests. It offers a fully equipped kitchen, free WiFi, a terrace, a garden, a spa, parking, and access to barbecue grills.
Charming Country Retreat - Madison, CT
9.5 4 reviews
Madison, CT
27/06 – 04/07
$537/nighttotal: $3759 (7 )

Charming Country Retreat

1 4
apartment , Clinton
This three-bedroom, two-bathroom house in Clinton offers exceptional privacy, nestled within a nature preserve and accessed via a long driveway; its proximity to specific Clinton landmarks requires further location details.
Sleeping eight guests, the property boasts a spacious open-plan living area with sliding glass doors leading to a deck, a luxurious primary bathroom with a skylighted dual shower, and a fully equipped kitchen including a fridge, microwave, and dishwasher; a garden completes this family-friendly retreat.

Best Madison, CT vacation rentals with a pool

Among the 105 accommodations in Madison, CT, here are the 4 best rentals with a pool

New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 68 reviews
Madison, CT
22/11 – 29/11
$1118/nighttotal: $7826 (7 )

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

4 2
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.
Resort Style Getaway W/pool, Spa, Game Room & More - Madison, CT
9.9 119 reviews
Madison, CT
11/07 – 18/07
$2192/nighttotal: $15344 (7 )

Resort Style Getaway W/pool, Spa, Game Room & More

5 4
apartment , East Haddam
This spacious home is located just 1.6 kilometres from the charming East Haddam Center, offering easy access to the Connecticut River, Gillette Castle, and the town beach. It has received excellent ratings for user experience, location, and cleanliness.
The property spans 418 square metres and comfortably accommodates up to 14 guests. Amenities include a private resort-style patio with a pool, hot tub, fireplace, fire pit, bar and grill, 65" TV, outdoor bathroom, and shower, a game room with a pool table, ping pong table, arcade basketball, poker table, and foosball, and a kitchen with a fridge, freezer, microwave oven, and dishwasher.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 10 reviews
Madison, CT
22/11 – 29/11
$761/nighttotal: $5327 (7 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
apartment , Killingworth
This holiday home is located in Killingworth, Connecticut, just a short drive from beaches, hiking trails, and lakes. It boasts excellent user, location, and cleanliness ratings.
This spacious property can accommodate up to 8 guests across 4 bedrooms and 2 bathrooms. Guests can enjoy a private pool, deck with a gas grill, fire pit, a walking trail, and a babbling brook, perfect for relaxing and enjoying the Connecticut weather.
The Killingworth Estate - Madison, CT
9.8 10 reviews
Madison, CT
23/06 – 26/06
$2632/nighttotal: $7896 (3 )

The Killingworth Estate

4 3
house , Killingworth
This 67-acre lakefront property is located in Killingworth, a short drive from the town centre and the Connecticut shoreline. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious house has four bedrooms and can sleep up to 11 guests. The property offers a range of amenities, including a swimming pool, tennis court, and a fully equipped kitchen.

Frequently Asked Questions about vacation rentals in Madison, CT

  • What should a first-time visitor not miss in Madison, CT?

    For a first-time visit, you should definitely check out the Madison Beach & the charming shops and restaurants on Boston Post Road. The historic town green is also a must-see, with the iconic Madison Town Hall.
  • What are the best Airbnb and vacation rentals in Madison, CT?

  • Which neighborhood in Madison, CT should you consider for a vacation rental?

    The area around the Madison Green is a great choice for a vacation rental. It's close to the beach, shops, and restaurants. Alternatively, the more residential neighbourhoods of North Madison or West Madison could be good choices if you prefer a quieter setting.
  • What are the most popular Airbnbs in Madison, CT?

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

    The Hammonasset Beach State Park is a fantastic spot for families, with a large beach, a playground, and a nature centre. The Madison Surf Club is a great place to learn to surf or just enjoy the beach.
  • What are the best vacation rentals with a pool in Madison, CT?

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

    The summer months are the busiest time in Madison, so booking your vacation rental in advance is essential. You can also find some good deals in the shoulder seasons, like spring and autumn, when the weather is still pleasant but the crowds are smaller.
  • What are the best rentals for families and kids in Madison, CT?

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

    The Madison Beach & Food Festival in July is a popular event, and the annual Madison Arts Festival in September is a great way to experience the local art scene. The nearby town of Guilford also hosts a number of events throughout the year, including the Guilford Fair in August.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

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

    The Madison Green is a great place to relax and enjoy the outdoors, and it's completely free. The Madison Historical Society offers free tours of the historic town hall, and the nearby Hammonasset Beach State Park has free access to the beach and trails.
  • What are the best restaurants with local dishes in Madison, CT?

    For a taste of local seafood, try The Lobster Shack on the waterfront. The Madison Beach Cafe is another popular spot for fresh seafood, and The Griswold Inn is a historic tavern that serves classic New England cuisine.
  • What are the best walking or cycling routes in Madison, CT?

    The scenic coastal path along the shoreline is a great option for walking or cycling. The Hammonasset Beach State Park also has a network of trails for hiking and biking.
  • Are there pet-friendly attractions in Madison, CT?

    Hammonasset Beach State Park is dog-friendly, and the nearby East River Park in Guilford also allows dogs on leash. Many restaurants and shops in Madison are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy than hotels, and they often have kitchen facilities, making it easier to cook your own meals. They can also be a more budget-friendly option, especially for larger families or groups.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison is known for its sailing and boating, with the Madison Yacht Club and the Madison Surf Club offering a range of activities. The town also has several parks and recreational facilities, including the Hammonasset Beach State Park, which has a variety of trails for hiking and biking.

Destinations nearby

Best Madison, CT vacation rentals with a balcony

Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews
Madison, CT
22/11 – 29/11
$866/nighttotal: $6062 (7 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
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.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
Madison, CT
24/06 – 28/06
$2118/nighttotal: $8472 (4 )

Stunning Historic Waterfront Mansion With Pool

5 8
apartment , Clinton
This historic 5-bedroom former Clinton Country Club Clubhouse offers direct waterfront views of Clinton Harbour and Meigs Point, situated less than 1 kilometre from Clinton's shops and restaurants.
This luxury flat accommodates up to 10 guests with a chef's kitchen featuring Sub-Zero appliances, a Gunite swimming pool, multiple decks, and private nanny quarters, all equipped with air conditioning, Wi-Fi, and parking.
Daniel Boone Meets Mid Century Modern Retreat\n - Madison, CT
10 24 reviews
Madison, CT
23/06 – 26/06
$1234/nighttotal: $3702 (3 )

Daniel Boone Meets Mid Century Modern Retreat\n

5 3
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.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
Madison, CT
22/11 – 29/11
$871/nighttotal: $6097 (7 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

4 2
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.

Best Madison, CT vacation rentals with parking

Madison Cozy Studio With Private Entrance - Madison, CT
9.8 580 reviews
Madison, CT
23/06 – 26/06
$208/nighttotal: $624 (3 )

Madison Cozy Studio With Private Entrance

1 3
studio , Madison
This self-contained apartment is situated in a peaceful residential area in Madison, Connecticut, just 5 kilometres from the beach and the Shoreline East train station. The accommodation has consistently received excellent ratings for its cleanliness, location, and overall experience.
The studio has a separate entrance and bathroom, offering privacy for up to 4 guests. Amenities include a small fridge, microwave, coffee maker, Wi-Fi, air conditioning, and a private outdoor space with a fire pit and patio furniture.
Shoreline Oasis - Madison, CT
9.2 7 reviews
Madison, CT
23/06 – 26/06
$360/nighttotal: $1080 (3 )

Shoreline Oasis

1 3
apartment , Clinton
This Clinton city-centre apartment offers easy access to the waterfront, train station, and Lobster Landing, with Hammonassett State Park and Chamard Vineyards within a short 8km drive.
The 51-square-metre self-contained flat comprises one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, Netflix/Hulu access, a terrace, and private parking.
Remodeled 4 Br Waterfront Beach House With All The Comforts Of Home...and More! - Madison, CT
9.8 20 reviews
Madison, CT
11/07 – 18/07
$803/nighttotal: $5621 (7 )

Remodeled 4 Br Waterfront Beach House With All The Comforts Of Home...and More!

4 4
apartment , Clinton
This charming beach house is located directly on the sand in Clinton, just a short drive from the town centre. The property has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has four bedrooms and one bathroom, comfortably accommodating eight guests. It includes a fully equipped kitchen, a private sandy beach, a rear porch with seating, and direct access to the beach.
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.6 9 reviews
Madison, CT
22/11 – 29/11
$700/nighttotal: $4900 (7 )

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

3 2
apartment , Madison
This Madison seaside property is situated less than 2km from Hammonasset Beach State Park, the Allis-Bushnell House and Museum, and the Scranton Memorial Library, with RJ Julia Booksellers and Anna Mia's also nearby.
This 372 square metre house offers four bedrooms, three bathrooms, sleeps six guests, and boasts a fully equipped kitchen, terrace, garden, parking, and air conditioning.
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