Madison, CT vacation rentalscozycozy

Compare Vacation Rentals & Airbnb in Madison, CT

156 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

156 Rentals and Airbnb in Madison, CT

Fortune Retreat - Madison, CT
9.8 16 reviews
Madison, CT
5 4
$1110/nighttotal: $5550 (5 )

Fortune Retreat

apartment - Guilford
This four-bedroom, three-bathroom Guilford apartment, near the I-95, Clinton Crossing Premium Outlets, and New Haven universities, offers easy access to Hammonasset Beach State Park (approximately 32km away).
The spacious property boasts an open-plan kitchen, dining, and living area, a lower-level family room, a private garden, parking, and sleeps up to eight guests, making it ideal for families or groups visiting the Guilford area.
Waterfrontthe Obstreperous Octopus - Madison, CT
10 4 reviews
Madison, CT
5 4
$1322/nighttotal: $6610 (5 )

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.
Stunning Historic Waterfront Mansion With Pool - Madison, CT
9.0 6 reviews
Madison, CT
5 5
$3094/nighttotal: $15470 (5 )

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.
New Madison Beach House - Ocean Front- Great Views- Booking Summer 2026 - Madison, CT
10 75 reviews
Madison, CT
6 4
$1015/nighttotal: $5075 (5 )

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

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
9.9 129 reviews
Madison, CT
6 5
$1914/nighttotal: $9570 (5 )

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

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.
Madison Beach House:  An Oasis On The Ct Shoreline - Madison, CT
10 1 review
Madison, CT
5 5
$1491/nighttotal: $7455 (5 )

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.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Madison, CT
9.6 12 reviews
Madison, CT
6 4
$838/nighttotal: $4190 (5 )

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.
Tranquil Lakefront Home @ Hidden Lake - Madison, CT
9.7 52 reviews
Madison, CT
5 4
$771/nighttotal: $3855 (5 )

Tranquil Lakefront Home @ Hidden Lake

apartment - Haddam
This lakefront house in Haddam is a short distance from the town centre, offering easy access to historic landmarks and local amenities. It has received excellent ratings for its cleanliness, location, and overall experience.
This spacious home can accommodate up to eight guests in its four bedrooms and one bathroom. Guests can enjoy a range of amenities, including a fire pit, a large garden, a dock, and a dedicated workspace, ensuring a comfortable and enjoyable stay.
Historic New England Home ,Reunions Beach Pass - Madison, CT
9.2 90 reviews
Madison, CT
6 4
$1136/nighttotal: $5680 (5 )

Historic New England Home ,Reunions Beach Pass

apartment - Guilford
This four-bedroom house is located in Guilford, within a 15-minute walk of the Guilford Art Center and Hyland House Museum, and less than 2km from the Henry Whitfield State Museum and Bishops Orchard and Winery. It has received excellent ratings from previous guests.
The property spans 186 square metres and can comfortably accommodate up to six guests. It features a garden, barbecue grills, a fully equipped kitchen, free Wi-Fi, a fireplace, and a terrace, perfect for enjoying the outdoors and relaxing after exploring the local area.
Clinton Beach House & Cottage W/ Pool, Near Shore - Madison, CT
9.9 23 reviews
Madison, CT
5 5
$954/nighttotal: $4770 (5 )

Clinton Beach House & Cottage W/ Pool, Near Shore

apartment - Clinton
This five-bedroom, three-bathroom house in Clinton is located a short distance (approximately 0.24 km) from the town's marinas and beach.
Sleeping up to 14 guests, this spacious property boasts a private in-ground pool, fully fenced backyard with fire pit, and is close to Clinton's waterside attractions.
2 Mi To Dtwn: 2-acre Retreat W/ Large Yard! - Madison, CT
9.5 2 reviews
Madison, CT
6 3
$777/nighttotal: $3885 (5 )

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

house - Madison
This three-bedroom house, perfect for eleven guests, is situated in Madison, Connecticut, a two-mile (3.2km) drive from the town centre and within walking distance of Hammonasset Beach State Park.
The 372-square-metre property boasts a fully equipped kitchen, three bathrooms, free Wi-Fi, and parking, with proximity to New Haven's attractions including Yale University and Tweed-New Haven Airport.
Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.2 5 reviews
Madison, CT
6 4
$940/nighttotal: $4700 (5 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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.

Best family friendly Madison, CT vacation rentals

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

Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck. - Madison, CT
10 61 reviews
Madison, CT
6 4
$1553/nighttotal: $7765 (5 )

Steps To Beach! Custom-built House With Panoramic Ocean Views, Wrap-around Deck.

apartment - Guilford
This apartment is located directly across the street from a sandy beach with a playground, offering stunning water views of Long Island Sound and is within walking distance of restaurants, bars, and shops. It has received excellent user ratings, making it a popular choice for travellers.
The apartment has four bedrooms and three bathrooms, accommodating up to eight guests, and offers a spacious open plan layout over 251 square metres. It includes a fully equipped kitchen, a wrap-around deck, a garden, a spa, a tennis court, parking, and a range of amenities for a comfortable stay, including kayaks, beach chairs, and outdoor games.
Blaidsdell House - Madison, CT
Madison, CT
5 3
$3014/nighttotal: $15070 (5 )

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.
Spacious 5 Br Home Near Town - Madison, CT
9.6 124 reviews
Madison, CT
5 5
$501/nighttotal: $2505 (5 )

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.
The Killingworth Estate - Madison, CT
9.8 12 reviews
Madison, CT
5 4
$2866/nighttotal: $14330 (5 )

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.

Best Madison, CT vacation rentals with a pool

Among the 156 accommodations in Madison, CT, here are the 4 best rentals with a pool

Private Pool! Getaway, 14 Mi To Hammonasset Beach - Madison, CT
9.8 11 reviews
Madison, CT
5 4
$791/nighttotal: $3955 (5 )

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.
Charming Beach Home, Complete With Pool & Cozy Guest House! - Madison, CT
9.8 49 reviews
Madison, CT
6 5
$1303/nighttotal: $6515 (5 )

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
Madison, CT
6 4
$905/nighttotal: $4525 (5 )

Private Pool! Getaway, 14 Mi To Hammonasset Beach

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
6 4
$1896/nighttotal: $9480 (5 )

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

Seaside Sanctuary Steps From Long Island Sound - Madison, CT
10 2 reviews
Madison, CT
6 4
$1284/nighttotal: $6420 (5 )

Seaside Sanctuary Steps From Long Island Sound

apartment - Westbrook
This Westbrook Centre holiday home, a block from Route 1 and five minutes from Route 95, offers easy access to Westbrook's downtown area, marina, and local restaurants.
The 260 square metre (2800 square feet) property boasts four bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, outdoor shower, ample parking, and proximity to the Katharine Hepburn Cultural Arts Center and Mashantucket Pequot Museum & Research Centre.
Duckling Crossing | Beach House On The Sand - Madison, CT
9.8 87 reviews
Madison, CT
6 4
$2471/nighttotal: $12355 (5 )

Duckling Crossing | Beach House On The Sand

apartment - Westbrook
This Westbrook beach house is located just 3 kilometres from Westbrook Town Beach, Clinton Town Beach, and Indian River Marina, offering easy access to the beautiful coastline. Guests consistently rate the property excellent for its location, cleanliness, and overall experience.
The property provides a comfortable stay for up to 9 guests in its 4 bedrooms and 2 bathrooms. The house features a fully equipped kitchen, a private fenced yard, a balcony with ocean views, a fireplace, and gas grills, making it perfect for families and groups looking to enjoy both indoor and outdoor spaces.
Coastal Getaway With Water Views In Every Room - Madison, CT
10 10 reviews
Madison, CT
6 3
$1096/nighttotal: $5480 (5 )

Coastal Getaway With Water Views In Every Room

apartment - Madison
This beachfront property in Madison, Connecticut, approximately 16km from Guilford, offers spectacular views of the Long Island Sound and is close to attractions such as the Deacon John Grave House and Scranton Memorial Library.
Sleeping six comfortably, this three-bedroom, one-bathroom apartment provides a fridge, dishwasher, air conditioning, parking, internet access, and is pet-friendly, ideal for families visiting the Guilford area.

Best Madison, CT vacation rentals with parking

Zakus Lake House - Madison, CT
9.9 34 reviews
Madison, CT
6 5
$1210/nighttotal: $6050 (5 )

Zakus Lake House

apartment - Clinton
This peaceful house is located in Clinton, just a short distance from the lake, offering a tranquil retreat from the hustle and bustle of everyday life. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has five bedrooms and two bathrooms, comfortably accommodating up to ten guests. The property features a private backyard with a BBQ, fire pit, and a full deck overlooking the serene lake, perfect for enjoying the peaceful surroundings and creating memorable moments with loved ones.
Purple Button Factory Sleeps 8, Walk To Town Green - Madison, CT
9.5 159 reviews
Madison, CT
5 4
$853/nighttotal: $4265 (5 )

Purple Button Factory Sleeps 8, Walk To Town Green

apartment - Guilford
This four-bedroom, two-bathroom house in Guilford, Connecticut, a former button factory dating back to 1860, is situated on a quiet street overlooking the Meadow River, a short walk (approximately 0.8 km) from Guilford Town Green.
The 209 m² property offers a fully equipped kitchen, sunroom, large garden with fire pit, and accommodates up to six guests; mid-week specials are available.
Coast And Country Private Estate - Madison, CT
10 20 reviews
Madison, CT
6 3
$960/nighttotal: $4800 (5 )

Coast And Country Private Estate

apartment - Guilford
This secluded 3-bedroom, 3-bathroom Yankee Barn residence offers exceptional privacy on a 8.1-hectare estate, located just a few kilometres from historic Guilford's shops and restaurants.
This family-friendly property provides direct access to walking trails, a kitchen with a fridge, microwave, and dishwasher, air conditioning, parking, and an excellent user rating for 6 guests.
Private Lake Hideaway Nestled In The Woods - Madison, CT
8.9 13 reviews
Madison, CT
5 4
$809/nighttotal: $4045 (5 )

Private Lake Hideaway Nestled In The Woods

apartment - Deep River
This four-bedroom property is located in Deep River, just a short distance from the town centre and its attractions, surrounded by private woodland and bordering state forests. The accommodation has received excellent user, location and cleanliness ratings.
The property has three bathrooms and can comfortably accommodate up to eight guests. It offers a private solarium, a deck, a master suite with panoramic views, exclusive lakefront access, and a tranquil and secluded setting.
©2026 cozycozy.com