Discover a selection of 262 holiday rentals in Madison, CT, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and air conditioning. Prices start at £ 129 per night, and houses and cottages are popular options for a stay in Madison. Either way, you'll find a rental 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 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.

Can I find a vacation rental around Madison?

Yes, our 2021 property listings offer a large selection of 262 vacation rentals near Madison. From 234 houses to 72 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Madison for a holiday or a weekend are on Vrbo.

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

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

  • Hammonasset Beach State Park: 778 vacation rentals
  • Scranton Memorial Library: 678 vacation rentals
  • Meigs Point Nature Center: 795 vacation rentals
  • Allis-Bushnell House and Museum: 681 vacation rentals
  • Anna Mia's: 678 vacation rentals

But there are many other points of interest around Madison listed on Vrbo UK 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. Vrbo UK has 234 Houses in Madison. Our other popular types of vacation rentals in Madison include:

  • Cottages: 72 rentals available
  • Bungalows: 72 rentals available
  • Cabins: 72 rentals available

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

Can I find a vacation rental with pool in Madison?

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