Vacation Rentals in Madison, CT

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

Explore Our Range of Family-Friendly Holiday Rentals in Madison, CT

Give everyone space to stretch out, cook, and unwind together at family holiday rentals in Madison, CT.

Summer Is Filling Up-beach, Shopping And Golf - Madison, CT
10 5 reviews

Summer Is Filling Up-beach, Shopping And Golf

apartment, Clinton
This seaside Clinton holiday home is situated within 3.2km of Bailey's Dog Park and Clinton Crossing Premium Outlets, and within 4.8km of Clinton Plaza Shopping Centre and the Adam Stanton House and General Store Museum.
This three-bedroom, three-bathroom property offers 177 square metres of space, accommodating up to six guests, and features a fully equipped kitchen, garden, terrace, free Wi-Fi, on-site arcade, and barbecue facilities.
Blaidsdell House - Madison, CT
No reviews

Blaidsdell House

house, Clinton
Blaidsdell House in Clinton is located 2.7 kilometres from Clinton Town Beach, offering convenient coastal access.
This spacious 427 square metre detached house accommodates up to 19 guests with 3 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, garden, terrace with sea views, fireplace, and free Wi-Fi.
Madison Beach House:  An Oasis On The Ct Shoreline - Madison, CT
10 1 review

Madison Beach House: An Oasis On The Ct Shoreline

apartment, Madison
This Madison beach house is located on a quiet street just 1.6km from the Long Island Sound and its beautiful beaches. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This spacious five-bedroom, three-bathroom home can comfortably accommodate up to eight guests. The apartment offers a fully equipped kitchen, a relaxing porch with views of the Long Island Sound, a private garden, and a barbecue for outdoor dining, as well as direct beach access and a range of local activities.
The Killingworth Estate - Madison, CT
9.8 12 reviews

The Killingworth Estate

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.

Popular Holiday Rentals with a Swimming Pool in Madison, CT

Spend your days alternating between the sun loungers and the water at holiday rentals with a pool in Madison, CT.

Charming Beach Home, Complete With Pool & Cozy Guest House! - Madison, CT
9.8 48 reviews

Charming Beach Home, Complete With Pool & Cozy Guest House!

apartment, Clinton
This B&B is situated just 1.5 kilometres from the water in Clinton, close to the marina and town beach, offering easy access to the area's attractions. The property has received excellent user ratings and is perfect for families or groups of friends looking for a comfortable and spacious stay.
The B&B comprises a 341 square metre main house with five bedrooms and four bathrooms, accommodating up to 14 guests. The property boasts a range of amenities, including a private swimming pool, a tennis court, and a fully equipped kitchen, as well as a private garden with a fire pit and an outdoor shower, making it ideal for both relaxation and entertainment.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 11 reviews

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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

    The Madison Beach is a must-visit for families, with its shallow waters and plenty of space for kids to play. The Hammonasset Beach State Park, just a short drive away, is another great option for a family day out, with its long sandy beach, playground, and nature trails.
  • What are the best Airbnb and holiday rentals in Madison, CT?

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

    You'll find the best deals on vacation rentals in the shoulder seasons, from April to May and September to October, when the weather is still pleasant but the crowds are smaller. If you want to experience the summer buzz, then book your rental in June, July or August, but be prepared to pay a premium.
  • What are the most popular Airbnbs in Madison, CT?

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

    A walk along the scenic coastline is a great way to enjoy Madison without spending any money. The Madison Green is also a lovely spot for a picnic lunch, and there are plenty of free events and activities taking place throughout the year.
  • What are the best holiday rentals with a pool in Madison, CT?

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

    Try the Lobster Roll at the Madison Beach Cafe, or the New England Clam Chowder at the The Griswold Inn. Both are classic local dishes, and they're delicious.
  • What are the best rentals for families and kids in Madison, CT?

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

    The Shoreline Greenway Trail is a great option for both walking and cycling, offering stunning views of the Long Island Sound. The Madison Green is a lovely spot for a leisurely stroll, and there are plenty of quiet residential streets perfect for a bike ride.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, CT?

    Family House Near Hammonasset Beach State Park and Sundrenched 5 Br Home W/ Private Dock Near Beaches are the best holiday rentals or Airbnb with a jacuzzi in Madison, CT.

  • Are there pet-friendly attractions in Madison, CT?

    Yes, the Madison Beach is pet-friendly, and there are plenty of dog-walking trails in the area. The Hammonasset Beach State Park also welcomes dogs, but they must be kept on a leash.
  • What are the benefits of choosing a vacation rental in Madison, CT?

    Vacation rentals offer more space and privacy than a hotel room, and they're often more affordable, especially for families or groups. You'll also have access to a kitchen, which can save you money on dining out.
  • What are the top sports attractions and facilities in Madison, CT?

    Madison has several public parks with sports facilities, including tennis courts, basketball courts, and baseball fields. The Madison Beach is also a popular spot for swimming, kayaking, and paddleboarding.

Popular destinations

Popular Holiday Rentals with a Terrace in Madison, CT

Find holiday rentals with a balcony in Madison, CT and wake up to ocean views.

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 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.
Charming Beach Home, Complete With Pool & Cozy Guest House! - Madison, CT
9.8 48 reviews

Charming Beach Home, Complete With Pool & Cozy Guest House!

apartment, Clinton
This B&B is situated just 1.5 kilometres from the water in Clinton, close to the marina and town beach, offering easy access to the area's attractions. The property has received excellent user ratings and is perfect for families or groups of friends looking for a comfortable and spacious stay.
The B&B comprises a 341 square metre main house with five bedrooms and four bathrooms, accommodating up to 14 guests. The property boasts a range of amenities, including a private swimming pool, a tennis court, and a fully equipped kitchen, as well as a private garden with a fire pit and an outdoor shower, making it ideal for both relaxation and entertainment.
Blaidsdell House - Madison, CT
No reviews

Blaidsdell House

house, Clinton
Blaidsdell House in Clinton is located 2.7 kilometres from Clinton Town Beach, offering convenient coastal access.
This spacious 427 square metre detached house accommodates up to 19 guests with 3 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, garden, terrace with sea views, fireplace, and free Wi-Fi.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
8.8 5 reviews

Stunning Historic Waterfront Mansion With Pool

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

Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly! - Madison, CT
No reviews

Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!

apartment, Clinton
This lakefront holiday home in Clinton is located in a wooded, natural setting, a 1-minute walk from beach-style lake access and a short distance from the Adam Stanton House and General Store Museum and Scranton Memorial Library.
This four-bedroom, four-bathroom flat accommodates up to eleven guests, featuring a two-level layout with a private deck, hot tub, and fireplace, with amenities including a fridge, microwave, and air conditioning.
Spacious 5 Br Home Near Town - Madison, CT
9.6 124 reviews

Spacious 5 Br Home Near Town

apartment, Guilford
This spacious five-bedroom farmhouse is situated in the Historic Guilford neighbourhood, approximately 1.6 kilometres from Guilford town centre and offers easy access to I-95.
The two-storey property sleeps ten guests, boasting a fully equipped kitchen with dishwasher, a garden, parking, and excellent proximity to hiking trails and a Pick Your Own farm.
Waterfrontthe Obstreperous Octopus - Madison, CT
10 4 reviews

Waterfrontthe Obstreperous Octopus

apartment, Clinton
This luxury waterfront flat in Clinton offers direct sea views and is within 500 meters of the shoreline, providing easy access to Clinton's town centre and Hammonasset Beach State Park.
This four-bedroom, two-bathroom apartment sleeps eight guests and features air conditioning, a garden, parking, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, ideal for coastal activities like kayaking.
Large Charming Historic House Close To Beaches - Madison, CT
9.8 47 reviews

Large Charming Historic House Close To Beaches

apartment, Clinton
This six-bedroom, two-bathroom house in Clinton, Connecticut is situated a short 2.4km walk from Clinton Town Beach, Adam Stanton House and General Store Museum, and Indian River Marina, and within 3.2km of Clinton Plaza Shopping Centre and Clinton Crossing Premium Outlets.
Sleeping up to eleven guests, this self-catering property boasts a fully equipped kitchen with fridge, microwave, and dishwasher, a patio, laundry facilities, and a Smart TV, offering convenient access to Clinton Station (a 1.1km walk).

Guest-Favourite High-End Rentals in Madison, CT

Bask in absolute tropical privacy with upscale coastal design at luxury holiday rentals in Madison, CT.

Waterfront Home 5 Night Min. Stay In July&aug - Madison, CT
9.4 7 reviews

Waterfront Home 5 Night Min. Stay In July&aug

apartment, Guilford

Popular Holiday Rentals in the CBD of Madison, CT

Stay steps away from local fish markets, surf shops, and seashore bars at holiday rentals in the heart of Madison, CT.

Lakehouse W/ Hot Tub In Clinton, Ct - Madison, CT
10 1 review

Lakehouse W/ Hot Tub In Clinton, Ct

apartment, Clinton
Waterfront Lakehouse Getaway In Clinton W/ Hot Tub - Madison, CT
8.6 26 reviews

Waterfront Lakehouse Getaway In Clinton W/ Hot Tub

apartment, Clinton
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
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.5 2 reviews

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

house, Madison

Popular Holiday Rentals by the Sea in Madison, CT

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Madison, CT.

Newly Renovated Clinton Beach House - Madison, CT
No reviews

Newly Renovated Clinton Beach House

apartment, Clinton
1 Block From Water - Welcoming 4 Bedroom Home - Madison, CT
9.9 32 reviews

1 Block From Water - Welcoming 4 Bedroom Home

apartment, Madison

Best-Rated Holiday Rentals with a Jacuzzi in Madison, CT

Watch the stars come out over the water while soaking in a steaming outdoor hot tub at island holiday rentals in Madison, CT.

Waterfront Lakehouse Getaway In Clinton W/ Hot Tub - Madison, CT
8.6 26 reviews

Waterfront Lakehouse Getaway In Clinton W/ Hot Tub

apartment, Clinton
Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly! - Madison, CT
No reviews

Waterfront Lakehouse W/hot Tub In Clinton, Ct. Pet-friendly!

apartment, Clinton
Lakehouse W/ Hot Tub In Clinton, Ct - Madison, CT
10 1 review

Lakehouse W/ Hot Tub In Clinton, Ct

apartment, Clinton
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