Destination guide

Elegant Madison will entice you

The beaches and surrounding scenery provide a peaceful ambiance to your vacation 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-sees in the area. A vacation 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 vacation home and experience everything that makes Madison a fun spot to vacation. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 83°F.

Natural features

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 vacation in Madison. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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

Traveling 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 center. 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 vacation rentals are available around Madison?

Our 2020 vacation rental listings offer a large selection of 323 house rentals around Madison. From 190 Houses to 92 Cottages, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Madison is on HomeAway.

What is the best area to stay when travelling to Madison?

Whether you're travelling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Madison:

  • Madison Center: 37 vacation rentals
  • Saybrook Manor: 35 vacation rentals
  • Momauguin: 23 vacation rentals
  • Dwight: 21 vacation rentals
  • Downtown: 27 vacation rentals

For other neighbourhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when travelling to Madison?

HomeAway offers a large selection of lodging choices near lovely places in Madison. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Hammonasset Beach State Park: 793 home rentals
  • Deacon John Grave House: 683 home rentals
  • Scranton Memorial Library: 693 home rentals
  • Meigs Point Nature Center: 829 home rentals
  • North Madison Shopping Center: 412 home rentals

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

Can I rent Houses in Madison?

Yes, of course. HomeAway has 190 Houses in Madison. Our other popular types of vacation rentals in Madison include:

  • Cottages: 92 lodging choices
  • Bungalows: 92 lodging choices
  • Condos/Apartments: 26 lodging choices

But you can also enjoy a great stay in one of our other vacation homes including Cabins and more.

Can I find a vacation rental with pool in Madison?

Yes, you can select your preferred vacation rental with pool among our 26 vacation homes with pool available in Madison.

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