Postcard Cabins Machimoodus, Outdoor Collection By Marriott Bonvoy
2 4
cabin , East Haddam
This East Haddam cottage is situated in a regional park, 1.1 kilometres from Machimoodus State Park and under 10 kilometres from the Goodspeed Opera House and Comstock Bridge. The self-catering lodge offers a kitchenette with a stove, private shower, patio, and free on-site parking, perfect for exploring nearby attractions such as Gillette Castle State Park and Cockaponset State Forest.
Madison, CT
27/06 – 04/07
SG$314/nighttotal: SG$2198 (7 )
Sachem's Head Cottage, Guilford, Ct
1 4
apartment , Guilford
This historic 1883 cottage in the Sachem's Head area of Guilford offers picturesque views of pasture, salt meadow, and Long Island Sound, providing a unique glimpse into shoreline living. This 74 square meter dwelling accommodates up to four guests and features front and back screen porches, an outdoor shower, and a compact kitchen with a microwave and hotplate, perfect for exploring the nearby Sachem's Head shoreline.
9.5 29 reviews
Madison, CT
12/10 – 20/10
SG$277/nighttotal: SG$2216 (8 )
Relax In A Cabin By The Beach (Cottage No.1)
1 2
apartment , Madison
This Madison cottage is situated near Madison's beach and greenway trail, a short drive (approximately 1.6 to 3.2 km depending on the specific location within Madison) from the town centre. The self-catering property sleeps two adults and a child, boasting a queen-size bed, a mini-fridge, coffee maker, microwave, toaster, and air conditioning; a pack 'n play is available for infants.
9.2 7 reviews
Madison, CT
12/10 – 20/10
SG$279/nighttotal: SG$2232 (8 )
Shoreline Oasis
1 2
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.
9.6 9 reviews
Madison, CT
22/11 – 29/11
SG$644/nighttotal: SG$4508 (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.
10 68 reviews
Madison, CT
22/11 – 29/11
SG$1028/nighttotal: SG$7196 (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.
10 56 reviews
Madison, CT
11/12 – 12/12
SG$1054/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.
Madison, CT
27/06 – 04/07
SG$605/nighttotal: SG$4235 (7 )
New Twin Tides Retreat- Two Homes For Your Group
3 4
apartment , Clinton
This apartment in Clinton is situated just five houses from a private beach, offering convenient access to local seafood restaurants such as Lenny & Joe’s Fish Tale and Bill’s Seafood, as well as Clinton Crossing Premium Outlets. This recently updated three-bedroom, two-bathroom dwelling accommodates up to seven guests, featuring a kitchen with a fridge and microwave, air conditioning, and a garden, with the added benefit of two separate houses for enhanced privacy during your stay.
Madison, CT
12/07 – 16/08
SG$574/nighttotal: SG$20090 (35 )
Modern Home In The Trees | 5 Min To Guilford Green
1 3
apartment , Guilford
This artist-owned flat offers a secluded forest setting on a stone slope, just 5 minutes from the historic Guilford Green with its 17th-century buildings, shops, and galleries, and a short 5-minute drive to Connecticut shoreline beaches. This well-appointed two-bedroom flat accommodates four guests, featuring two king beds, two bathrooms, a fully equipped kitchen with a fridge, freezer, and dishwasher, air conditioning, Wi-Fi, and a private deck with a grill and picnic table, plus a beach pass for easy access to local beaches and proximity to Westwood Hiking Trails and Bishop's Orchards.
10 2 reviews
Madison, CT
12/10 – 20/10
SG$274/nighttotal: SG$2192 (8 )
Quiet Killingworth Rental W/ Deck & Grill!
1 2
apartment , Killingworth
This apartment is located in Killingworth, just 6 kilometres from Cockaponset State Forest, Sundial Herb Garden, and Chatfield Hollow State Park, and within 9 kilometres of Millers Pond State Park and North Madison Shopping Centre. The peaceful setting offers easy access to nature and local amenities. The self-catering apartment has a fully equipped kitchen with an oven, stovetop, and microwave, as well as a TV, ceiling fan, and iron/ironing board. Guests can enjoy complimentary Wi-Fi and parking, and the smoke-free building provides a comfortable and clean environment.
9.8 67 reviews
Madison, CT
02/08 – 07/08
SG$433/nighttotal: SG$2165 (5 )
The Davis House
3 4
apartment , Guilford
This spacious three-bedroom house is located in a peaceful neighbourhood in Guilford, Connecticut, just 1.6 kilometres from the historic town green and 0.8 kilometres from Interstate 95. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house has three bathrooms and can accommodate up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a large fenced garden, and parking. Guests can also enjoy outdoor activities such as hiking, biking, and kayaking, all within a short drive.
Madison, CT
23/06 – 26/06
SG$590/nighttotal: SG$1770 (3 )
Tranquil Two Bedroom Home Near Shoreline
1 3
apartment , Madison
This charming two-bedroom house is ideally located in the heart of Madison, just a short distance from the city's vibrant Shoreline beaches, restaurants, and shops. The surrounding area offers a mix of residential streets and local businesses, creating a peaceful yet convenient setting for your stay. The house comfortably accommodates up to four guests and features a spacious living room with a grand piano, a separate sitting room, a dining room, and a fully equipped kitchen. Enjoy the outdoor space with a back deck, patio furniture, and a gas BBQ grill, perfect for relaxing evenings and al fresco dining.
Best Madison, CT lodgings with a pool
Among the 113 accommodations in Madison, CT, here are the 4 best ones with a pool
10 7 reviews
Madison, CT
12/10 – 20/10
SG$1901/nighttotal: SG$15208 (8 )
Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond
4 2
house , Killingworth
This luxurious four-bedroom apartment is situated in Killingworth, Connecticut, just 15 kilometres from shops, restaurants, and the Connecticut shoreline. It is rated excellent by previous guests and offers a peaceful retreat in a secluded natural setting. The property spans 334 square metres and comfortably accommodates up to 10 guests. Enjoy a range of amenities, including a heated swimming pool, a Jacuzzi, a private tennis court, and a fully equipped kitchen with top-of-the-line appliances.
9.8 43 reviews
Madison, CT
12/10 – 20/10
SG$1173/nighttotal: SG$9384 (8 )
Charming Beach Home, Complete With Pool & Cozy Guest House!
5 2
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.
Madison, CT
23/06 – 26/06
SG$2029/nighttotal: SG$6087 (3 )
Luxury 75ft Yacht With Captain, Flybridge With Bar, 4 Ensuite Staterooms.
4 3
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.
Madison, CT
12/07 – 16/08
SG$189/nighttotal: SG$6615 (35 )
Stay Aboard Mini-expedition Trawler Mary South
2 3
boat , Clinton
The Mary South, a unique mini-expedition ship, is docked at Clinton Yacht Haven, offering convenient access just 1.6 kilometres from Hammonnasset Beach and State Park. This vessel provides accommodation for four guests, featuring two bedrooms and two bathrooms, with amenities including air conditioning, internet, a kitchen, and access to the yacht haven's swimming pool and clubhouse.
Best family friendly Madison, CT lodging
Among the 113 accommodations in Madison, CT, here are the 4 best for families
10 111 reviews
Madison, CT
12/10 – 20/10
SG$450/nighttotal: SG$3600 (8 )
Shabby Chic Retreat
1 2
apartment , Madison
Greenfield Cottage is located in a quiet neighbourhood in Madison, Connecticut, just 6.5km from Hammonasset State Park & Beach and close to Chatfield Hollow. The property enjoys excellent ratings for location, cleanliness, and overall user experience. This charming cottage offers a separate studio apartment with a private entrance and garden space for guests who desire privacy. The accommodation can comfortably sleep up to four people and comes equipped with a kitchen, a garden, parking, laundry facilities, and a keypad lock for easy access.
10 5 reviews
Madison, CT
12/10 – 20/10
SG$1385/nighttotal: SG$11080 (8 )
Beachfront Cottage With Panoramic Views Of Long Island Sound In Madison Ct
6 2
cottage , Madison
The Bunce Cottage, a six-bedroom holiday home in Madison, Connecticut, enjoys direct Seaview Beach access via a boardwalk and is near Hammonasset Beach State Park. This 261 square metre property sleeps twelve guests and boasts a fully equipped kitchen, three bathrooms, a large screened porch, a double lot with space for outdoor games, and a detached two-car garage; water activities such as jet skiing and kayaking are readily available nearby.
9.9 82 reviews
Madison, CT
22/11 – 29/11
SG$354/nighttotal: SG$2478 (7 )
The Rising Tide Cottage
1 2
house , Madison
The Rising Tide Cottage is situated in a peaceful neighbourhood on the Connecticut shoreline, less than 1.6 kilometres from downtown Madison. The cottage boasts excellent ratings for location, cleanliness and user experience. The cottage has one bedroom and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, Wi-Fi, and complimentary beach chairs and towels for use at the nearby Pent Road Beach.
9.7 29 reviews
Madison, CT
11/12 – 12/12
SG$756/nightfor 1 night
Perfect Cape Beach Cottage In Madison Ct!
1 6
apartment , Madison
This Madison, Connecticut beach cottage offers deeded access to a private sandy beach, located steps from the shore in a quiet neighbourhood. The two-bedroom, two-bathroom property sleeps six, features a full kitchen with freezer and dishwasher, a private backyard, patio, wraparound deck, and air conditioning; note that bedrooms are upstairs via a spiral staircase.
Frequently asked questions about accommodations in Madison, CT
What are the most convenient modes of transportation within Madison, CT?
Madison is a relatively small town, and most places are within walking distance. You can also get around by bicycle, as there are dedicated bike paths throughout the town. If you need to travel further afield, the Shoreline East train line stops in Madison and connects you to other towns along the Connecticut coast.
What outdoor activities and adventures are popular in and around Madison, CT?
Madison is a haven for outdoor enthusiasts. The coastal location offers plenty of opportunities for kayaking, paddleboarding, and sailing. The Hammonasset Beach State Park has hiking trails and a nature centre. For a more challenging adventure, try rock climbing at East Rock Park in nearby New Haven.
What are the best accommodations with a pool in Madison, CT?
What types of accommodations are available in Madison, CT?
Madison offers a range of accommodation options. There are several charming bed and breakfasts, as well as a handful of hotels and motels. If you're looking for a more private experience, you can find vacation rentals on the coast or in the countryside.
What are the best accommodations with a jacuzzi in Madison, CT?
The best time to visit Madison is during the summer months, from June to August, when the weather is warm and sunny and the beaches are bustling. However, if you prefer a quieter experience, spring or autumn can be lovely, with mild temperatures and vibrant foliage.
What are the best accommodations for families and kids in Madison, CT?
In which part of Madison, CT should you consider renting accommodation?
If you're looking to be close to the beach, consider renting accommodation in the Madison Beach area. For a more central location, the village centre on the Madison Green is a good choice. If you prefer a quieter experience, the residential neighbourhoods further inland offer a peaceful retreat.
What are the best pet friendly accommodations in Madison, CT?
The Millhouse Downtown Chester is situated in the centre of Chester, just 8km from the Goodspeed Opera House and 27km from Wesleyan University. This apartment has received excellent ratings for its location, cleanliness and overall experience. The accommodation is a 2-bedroom, 2-bathroom apartment spanning 102 square metres. The property offers a range of amenities including a fully equipped kitchen, private parking, a terrace with river views, an outdoor fireplace, and access to streaming services.
10 1 review
Madison, CT
02/08 – 07/08
SG$893/nighttotal: SG$4465 (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.
10 24 reviews
Madison, CT
23/06 – 26/06
SG$1135/nighttotal: SG$3405 (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.
10 5 reviews
Madison, CT
12/10 – 20/10
SG$650/nighttotal: SG$5200 (8 )
Newly Renovated Carriage House Near Town & Beaches
2 2
apartment , Madison
This newly renovated carriage house is located in Madison, just 11 kilometres from Hammonasset Beach and within easy reach of Thimble Islands, City Hall and Yale University. The apartment has received excellent ratings for location, cleanliness and user experience. The property offers two bedrooms and one bathroom, providing comfortable accommodation for up to four guests across 58 square metres. The apartment includes a private terrace, a garden, free Wi-Fi, a fully equipped kitchen, air conditioning and private parking.
Best Madison, CT accommodations with a kitchen
8.7 6 reviews
Madison, CT
22/11 – 29/11
SG$148/nighttotal: SG$1036 (7 )
Stylish Modern Tiny Stay Steps From The Ocean
1 2
house , Clinton
This modern guest house is located in Clinton, a short 50-meter walk from the ocean, offering easy access to local shops and beaches. This one-bedroom, one-bathroom property accommodates two guests and features air conditioning, a fridge, a microwave, and on-site parking, making it ideal for couples or solo travellers.
10 2 reviews
Madison, CT
27/06 – 04/07
SG$705/nighttotal: SG$4935 (7 )
New Coastal Cottage 2 Miles To Beach + Lake Access
2 4
apartment , Clinton
This newly refurbished flat is located 3.2 kilometres from Hammonassett Beach and downtown Madison, and a short walk to Boulder Lake Beach, also offering proximity to downtown Clinton. This two-bedroom flat accommodates up to six guests and features air conditioning, a kitchen, Wi-Fi, a screened-in porch with outdoor dining, and a fire pit for evening relaxation.
Madison, CT
23/06 – 26/06
SG$536/nighttotal: SG$1608 (3 )
New Charming Coastal Bungalow Steps From The Beach
1 3
apartment , Madison
This newly remodelled two-bedroom flat offers exceptional proximity to the beach, just 152 metres away, and is conveniently situated 2.4 kilometres from downtown Madison, providing easy access to local shops and restaurants, whilst being mere minutes from Hammonasset Beach State Park. Accommodating up to six guests, this coastal getaway features two queen beds and a pull-out sofa, a full bathroom with a walk-in shower, private driveway parking for two vehicles, and is located in a quiet, walkable neighbourhood.
10 15 reviews
Madison, CT
11/07 – 18/07
SG$443/nighttotal: SG$3101 (7 )
Enjoy A Taste Of New England In Historic Guilford Ct
2 4
apartment , Guilford
This charming house is situated in central Guilford, just a short walk from the Guilford Art Center and Hyland House Museum. It has received excellent user ratings, making it a popular choice for travellers. The property has two bedrooms and a sofa bed, comfortably accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, a patio, a garden, a spa, and parking.