Discover a selection of 253 holiday home rentals in Madison, CT, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and air conditioning. Prices start at AU$ 229 per night, and holiday houses and cottages are popular options for a stay in Madison. Either way, you'll find holiday accommodation for everyone's needs.
Destination guide

Luxury Madison will entice you

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Madison. Renowned for its fishing, aquarium and cheese shops, this city welcomes all visitors. East Rock Park and Yale Bowl are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Sightseeing in and around Madison

Are you looking for top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Madison a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (3.2 mi / 5.1 km)
  • Chamard Vineyards (4.5 mi / 7.2 km)
  • Bishops Orchard and Winery (4.6 mi / 7.4 km)
  • Connecticut Sportsplex (10.1 mi / 16.3 km)
  • Gouveia Winery (10.7 mi / 17.2 km)
  • Paradise Hills Vineyard (11.2 mi / 18 km)

Seasonal weather in Madison

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 28°F.

Natural highlights

Exploring the natural landscape of Madison

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Madison. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • East Rock Park (14.6 mi / 23.5 km)
  • Chatfield Hollow State Park (3.2 mi / 5.1 km)
  • Chaffinch Island State Park (5.1 mi / 8.2 km)
  • Hammonasset Beach State Park (5.2 mi / 8.4 km)
  • Plattwood Park (8.7 mi / 14 km)
  • Cockaponset State Forest (9.1 mi / 14.7 km)
How to get there

Travelling to and around Madison

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 14.5 mi (23.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Oxford, CT (OXC-Waterbury - Oxford), which is 28.7 mi (46.2 km) away.

How many holiday accommodation are available around Madison?

Our 2021 accommodation listings offer a large selection of 253 holiday rentals around Madison. From 225 holiday houses to 66 cottages, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Madison is on Stayz.

What are the most popular points of interest and landmarks to stay near when travelling to Madison?

Stayz offers a large selection of holiday homes near great places in Madison. From Stayz travellers, the most popular points of interest to stay near are:

  • Deacon John Grave House: 645 holiday rentals
  • Hammonasset Beach State Park: 764 holiday rentals
  • Meigs Point Nature Center: 778 holiday rentals
  • Allis-Bushnell House and Museum: 663 holiday rentals
  • Anna Mia's: 664 holiday rentals

But there are many other points of interest around Madison listed on Stayz where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Madison?

Yes, of course. Stayz offers 225 Houses in Madison. Our other popular types of Madison holiday rentals include:

  • Cottages: 66 holiday houses
  • Bungalows: 66 holiday houses
  • Cabins: 66 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Condos/Apartments and more.

Can I find a holiday accommodation with pool in Madison?

Yes, you can select your preferred holiday accommodation with pool among our 23 holiday homes with pool available in Madison. Please use our search bar to access the selection of holiday rentals available.