Holiday Rentals in Madison, CT

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Madison, CT holiday rentals
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105 Holiday rentals and Airbnb in Madison, CT

Best family friendly Madison, CT holiday rentals

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

Charming Country Retreat - Madison, CT
9.5 4 reviews
Madison, CT
27/06 – 04/07
332 €/nighttotal: 2324 € (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.
Grace Island.  \Nprivate Island!  Vacations, Getaways, Weddings & Special Events. - Madison, CT
Madison, CT
24/06 – 28/06
6522 €/nighttotal: 26088 € (4 )

Grace Island. \Nprivate Island! Vacations, Getaways, Weddings & Special Events.

11 8
apartment , Branford
Grace Island, a short distance off the coast of Branford, Connecticut, offers a secluded escape just a stone's throw from Farm River State Park and West Rock Ridge State Park. This historic island, built in 1850, provides a unique blend of history and modern comfort.
The 604 square metre property boasts 11 bedrooms, 6 bathrooms, and can accommodate up to 22 guests. Grace Island offers a range of amenities including a fully equipped kitchen, a spacious garden, a tennis court, and a terrace, perfect for enjoying the island's natural beauty.
Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 24 reviews
Madison, CT
23/06 – 26/06
764 €/nighttotal: 2292 € (3 )

Daniel Boone Meets Mid Century Modern Retreat

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.
Cheerful 4br Home-7 Min Walk To Private Beach - Madison, CT
9.8 21 reviews
Madison, CT
22/11 – 29/11
500 €/nighttotal: 3500 € (7 )

Cheerful 4br Home-7 Min Walk To Private Beach

1 2
apartment , Madison
This four-bedroom, three-bathroom apartment in Kelsey Place, Madison, offers easy access to a private beach, the precise distance requiring further clarification regarding Kelsey Place's location relative to Madison landmarks.
Sleeping up to ten guests, the property features a spacious layout including a master suite with private balcony and a ground floor bedroom with en-suite bathroom, boasting modern amenities such as a dishwasher and air conditioning, alongside a garden and parking.

Best Madison, CT holiday rentals with a pool

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

Roof Top Pool, Ocean Views, Private Beach! - Madison, CT
Madison, CT
12/07 – 16/08
681 €/nighttotal: 23835 € (35 )

Roof Top Pool, Ocean Views, Private Beach!

1 3
apartment , Clinton
This Clinton flat, situated at the highest point of the shoreline, offers direct, private beach access and unparalleled panoramic ocean views, with sunrises and sunsets over the water.
Boasting old-world charm and rustic luxury, this Mediterranean-inspired dwelling accommodates up to five guests across two bathrooms, featuring a private plunge pool, outdoor shower, on-site kayaking, and potential discounts on Blue Heron Cruises.
The Killingworth Estate - Madison, CT
9.8 10 reviews
Madison, CT
24/06 – 28/06
1836 €/nighttotal: 7344 € (4 )

The Killingworth Estate

4 8
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.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
Madison, CT
22/11 – 29/11
539 €/nighttotal: 3773 € (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.
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms. - Madison, CT
Madison, CT
27/06 – 04/07
1335 €/nighttotal: 9345 € (7 )

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

4 4
houseboat , Clinton
This houseboat is situated in Clinton, Connecticut, offering convenient access to RJ Julia Booksellers, located just 300 meters away, and is within easy reach of Clinton Crossing Premium Outlets and Clinton Plaza Shopping Center.
This four-bedroom, four-bathroom vessel accommodates up to eight guests, featuring a king bed, queen bed, and two twin beds, complete with air conditioning and internet, and boasts a flybridge bar and aft deck dining area for enjoying panoramic views.

Frequently asked questions about holiday rentals in Madison, CT

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

    You definitely shouldn't miss the scenic beauty of Hammonasset Beach State Park, a popular spot for swimming, sunbathing, and picnicking. The Madison Historical Society Museum is also worth a visit, showcasing the town's rich history and culture.
  • What are the best Airbnb and holiday 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 option for a vacation rental, with its charming shops, restaurants, and proximity to the beach. It's also close to the historic town centre and offers a vibrant, lively atmosphere.
  • What are the most popular Airbnbs in Madison, CT?

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

    The Children's Museum of Southeastern Connecticut in nearby New London is a great choice for families, offering interactive exhibits and educational activities. Hammonasset Beach State Park is also a popular destination, with its sandy beach, playground, and nature trails.
  • What are the best holiday rentals with a pool in Madison, CT?

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

    To avoid peak season crowds and secure the best deals, it's recommended to book your vacation rental in Madison during the shoulder seasons, from April to May or September to October, 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?

    Madison's annual July 4th celebration is a highlight, with a parade, fireworks, and live music. The Guilford Fair, held in late August, is another popular event, featuring agricultural exhibits, live entertainment, and carnival rides.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

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

    A stroll along the scenic Madison shoreline is a free and enjoyable activity. The Madison Green is another great option, offering a tranquil setting for a picnic or simply relaxing outdoors.
  • What are the best restaurants with local dishes in Madison, CT?

    The Lobster Landing Restaurant is a local favourite, serving fresh seafood dishes, including their renowned lobster rolls. The Madison Beach Hotel also offers a fantastic dining experience with its elegant setting and locally sourced ingredients.
  • What are the best walking or cycling routes in Madison, CT?

    The Shoreline Greenway Trail, a multi-use path, offers scenic walking and cycling routes along the Connecticut coastline. The Madison Green to Hammonasset Beach State Park route is a popular choice, offering a combination of urban and coastal scenery.
  • Are there pet-friendly attractions in Madison, CT?

    Hammonasset Beach State Park welcomes leashed dogs on designated areas of the beach. The Madison Green also allows dogs on leash, providing a pleasant spot for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy compared to hotels, often with kitchens and living areas. They also provide a more home-like atmosphere and can be more budget-friendly, especially for larger groups or families.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison is home to the Madison Beach & Yacht Club, offering a variety of water sports activities, including sailing, swimming, and kayaking. The town also has several public parks with sports fields and courts for basketball, tennis, and other activities.

Destinations nearby

Best Madison, CT holiday rentals with a balcony

Cozy Garden Apartment Along The Shoreline - Madison, CT
9.6 69 reviews
Madison, CT
22/11 – 29/11
179 €/nighttotal: 1253 € (7 )

Cozy Garden Apartment Along The Shoreline

1 2
apartment , Guilford
This one-bedroom apartment is located in Guilford, Connecticut, a short drive from New Haven's City Hall and Thimble Islands, offering a peaceful retreat away from the city's bustle. Guests consistently praise the apartment's excellent cleanliness, location, and overall experience.
The apartment spans 400 square metres and includes a fully equipped kitchen, a private patio with garden views, and access to a range of amenities including a Jacuzzi, spa, and parking. Enjoy windsurfing and fishing nearby, relax on the terrace, or simply unwind with streaming services and complimentary Wi-Fi.
Bliss By The Sea - Cozy Beachside Escape - Madison, CT
10 1 review
Madison, CT
02/08 – 07/08
601 €/nighttotal: 3005 € (5 )

Bliss By The Sea - Cozy Beachside Escape

2 4
apartment , Clinton
This Clinton waterfront apartment, situated in the Harborview Beach Association community, offers easy walking or cycling access to the beach and proximity to local landmarks such as the Adam Stanton House and General Store Museum.
The two-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, Roku TVs, a spacious back deck with gas grill, and ample parking; enjoy nearby attractions like the Allis-Bushnell House and Museum and RJ Julia Booksellers.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.6 10 reviews
Madison, CT
22/11 – 29/11
417 €/nighttotal: 2919 € (7 )

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger

4 2
apartment , Killingworth
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.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
Madison, CT
23/06 – 26/06
1313 €/nighttotal: 3939 € (3 )

Stunning Historic Waterfront Mansion With Pool

5 3
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.

Best Madison, CT holiday rentals with parking

Shoreline Oasis - Madison, CT
9.2 7 reviews
Madison, CT
23/06 – 26/06
223 €/nighttotal: 669 € (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.
1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach - Madison, CT
Madison, CT
02/08 – 07/08
458 €/nighttotal: 2290 € (5 )

1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach

2 4
apartment , Westbrook
This ground-floor flat in Westbrook Centre offers convenient access, being a 4-minute drive from West Beach and less than 1 kilometre from Westbrook Outlets.
This 50 square metre apartment sleeps up to four guests and features two bedrooms, one bathroom, a kitchen with a dishwasher, air conditioning, and dedicated parking, serving as an ideal base for exploring the shoreline.
Coral Cottage - In Clinton Harbor! - Madison, CT
Madison, CT
22/11 – 29/11
384 €/nighttotal: 2688 € (7 )

Coral Cottage - In Clinton Harbor!

3 2
apartment , Clinton
This boutique cottage in Clinton, CT, is a short 300-meter walk from the harbour, boat launch, and waterfront dining establishments including Shanks, Rocky's Aqua, and Lobster Landing, offering convenient access to local attractions such as the Adam Stanton House and General Store Museum.
This 139 square meter residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and three provided kayaks for exploring the local waterways.
Cozy Maple Tree Cabin - Situated On 6 Private Acres- Enjoy Nature - Madison, CT
10 56 reviews
Madison, CT
11/12 – 12/12
709 €/nightfor 1 night

Cozy Maple Tree Cabin - Situated On 6 Private Acres- Enjoy Nature

3 6
cabin , Killingworth
This charming lodge is situated in a peaceful rural area of Killingworth, just a short drive from attractions like the Adam Stanton House and General Store, Connecticut Valley Railroad State Park Trail, and Hammonasset Beach State Park. It is a great base for exploring the local history and natural beauty of the area.
The lodge spans 158 square metres and comfortably accommodates up to 8 guests in its three bedrooms and two bathrooms. The lodge offers a fully equipped kitchen, modern amenities like free high-speed Wi-Fi and a smart TV, as well as an outdoor patio for relaxing and enjoying the fresh air.
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