Compare Vacation Rentals & Airbnb in Madison, CT

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

Best family friendly Madison, CT vacation rentals

Among the 156 accommodations in Madison, CT, here are the 4 best family friendly rentals

@Get_yurty W/ 2 Sleeping Pods, No Cleaning/pet Fee - Madison, CT
9.9 98 reviews

@Get_yurty W/ 2 Sleeping Pods, No Cleaning/pet Fee

yurt, Killingworth
This yurt is situated in a beautiful treelined area of Killingworth, Connecticut, just a short distance from the town centre and a scenic drive from the Connecticut coastline. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The roundhouse sleeps up to four guests in two bedrooms with a full bathroom. You'll enjoy modern amenities including a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, parking, and internet access.
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 Westbrook flat is centrally located in Westbrook Centre, a four-minute drive from West Beach and less than 1 kilometre from the Westbrook Outlets.
This one-bedroom, 50-square-metre flat accommodates up to four guests and features a Level 2 EV charger, off-street parking, air conditioning, a kitchen with a fridge, microwave, and dishwasher, and a spacious living area with a 55-inch television.
Beach With Free Pass! Shopping Outlets And Golf! - Madison, CT
9.6 84 reviews

Beach With Free Pass! Shopping Outlets And Golf!

apartment, Clinton
This apartment is located in Madison, Connecticut, just a short drive from Clinton, with easy access to 15 miles of beach, downtown Madison, and premium outlets within 8 kilometres. The property has excellent user, location and cleanliness ratings, making it a highly recommended choice for travellers.
The apartment offers comfortable accommodation for up to 6 guests with multiple bedrooms, a game room and a sunroom with a deck. It comes with a fully equipped kitchen, air conditioning, a private garden, parking and internet access, providing everything you need for a relaxing and enjoyable stay.
Quiet Killingworth Rental W/ Deck & Grill! - Madison, CT
10 14 reviews

Quiet Killingworth Rental W/ Deck & Grill!

apartment, Killingworth
This Killingworth seaside flat is situated 15km from attractions including the Sundial Herb Garden and Chatfield Hollow State Park.
The 89 square metre self-catering apartment sleeps four, boasting a fully equipped kitchen, Wi-Fi, parking, and a playground nearby.

Best Madison, CT vacation rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 2 best rentals with a pool

Roof Top Pool, Ocean Views, Private Beach! - Madison, CT
8.3 6 reviews

Roof Top Pool, Ocean Views, Private Beach!

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.
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 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.

Popular destinations

Best Madison, CT vacation rentals with a balcony

Bliss By The Sea - Cozy Beachside Escape - Madison, CT
10 1 review

Bliss By The Sea - Cozy Beachside Escape

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.
Shoreline Oasis - Madison, CT
9.4 8 reviews

Shoreline Oasis

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.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.8 11 reviews

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

apartment, Haddam
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.
Daniel Boone Meets Mid Century Modern Retreat - Madison, CT
10 27 reviews

Daniel Boone Meets Mid Century Modern Retreat

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.

Best Madison, CT vacation rentals with parking

Amazing 2br Riverfront Gem - Madison, CT
9.8 182 reviews

Amazing 2br Riverfront Gem

apartment, Clinton
This charming cottage in Clinton, Connecticut is just a short distance from the beach, shops and restaurants, making it the perfect base for exploring this picturesque New England town. The property has consistently received excellent reviews from guests for its cleanliness, location and overall experience.
The cottage has two bedrooms and one bathroom, comfortably sleeping up to six guests. Guests can enjoy a well-equipped kitchen, a relaxing garden with a fairy-lit lawn and a wishing well, and a complimentary bottle of champagne on arrival.
1st Floor Westbrook Anchor | 2 Queen Beds | Ev Charger | Near Beach - Madison, CT
No reviews

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

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.
One Bedroom Apt-cristys Madison - Madison, CT
9.8 17 reviews

One Bedroom Apt-cristys Madison

apartment, Madison
This one-bedroom apartment is located just a minute's walk from two beaches and within easy walking distance of the town centre, shops and weekly events. It has excellent user, location and cleanliness ratings.
The apartment can comfortably accommodate up to four guests and features a fully equipped kitchen with a Keurig coffee machine, free cable/Roku and WiFi, a garden and parking. It also welcomes well-behaved dogs and has an on-site restaurant serving breakfast, lunch and dinner.
3br Waterfront Oasis On Joshua Cove, Private Beach - Madison, CT
10 40 reviews

3br Waterfront Oasis On Joshua Cove, Private Beach

apartment, Guilford
This waterfront flat in Guilford offers direct access to a private beach on the Long Island Sound, with unobstructed water views and stunning sunset vistas, located just 5 minutes by car from downtown Guilford.
This newly renovated three-bedroom apartment accommodates up to seven guests and features a fully equipped kitchen, a spacious living room with a fireplace, a garden with a dining area for eight, a basement game room with ping pong and cornhole, and a private gym.
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