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 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 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 rentals are available around Madison?

Our 2020 accommodation listings offer a large selection of 319 holiday lettings around Madison. From 187 houses to 92 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Madison:

  • Madison Center: 39 holiday homes
  • Downtown: 34 holiday homes
  • Westbrook Center: 67 holiday homes
  • Silver Beach: 48 holiday homes
  • Saybrook Manor: 38 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Madison? offers a large selection of holiday accommodations near great places in Madison. From travellers, the most popular points of interest to stay near are:

  • Hammonasset Beach State Park: 814 holiday lettings
  • Scranton Memorial Library: 708 holiday lettings
  • Meigs Point Nature Center: 852 holiday lettings
  • Allis-Bushnell House and Museum: 709 holiday lettings
  • Anna Mia's: 708 holiday lettings

But there are many other points of interest around Madison listed on 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. offers 187 Houses in Madison. Our other popular types of Madison holiday rentals include:

  • Cottages: 92 self catering accommodations
  • Bungalows: 92 self catering accommodations
  • Cabins: 92 self catering accommodations

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

Can I find a holiday accommodation with pool in Madison?

Yes, you can select your preferred holiday accommodation with pool among our 30 holiday homes with pool available in Madison. Please use our search bar to access the selection of holiday rentals available.

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