Photo by Shannon Willitts

Madison holiday homes

We found 415 holiday rentals — enter your dates for availability

Select from 36 homes, 11 cottages and other holiday rentals in Madison to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Head to the luxury city of Madison

The beaches and other outdoor surroundings create an inviting atmosphere in Madison. Renowned for its fishing, aquarium and cheese shops, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Madison

Do you want to find attractions to visit in the city? Venture out of your holiday home and experience everything that makes Madison a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Powder Ridge Mountain Park and Resort (16.6 mi / 26.7 km)
  • Kontokosta Winery (16.6 mi / 26.7 km)
  • Sparkling Pointe (17.6 mi / 28.3 km)
  • Sannino's Bella Vita Vineyard (18.5 mi / 29.8 km)
  • Raphael Winery (19 mi / 30.6 km)

Exploring the natural features in Madison

Whether you're an active traveller or just want to appreciate the scenery, Madison is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Clinton Town Beach (3.5 mi / 5.6 km)
  • Hammonasset Beach (3.5 mi / 5.7 km)
  • Westbrook Town Beach (6.3 mi / 10.2 km)
  • Chalker Beach (8.9 mi / 14.3 km)
  • Harvey's Beach (9.5 mi / 15.3 km)
  • Goose Island (12 mi / 19.4 km)

Seasonal weather averages 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 21°C.

Transport to and around Madison

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 16.5 mi (26.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into New London, CT (GON-Groton - New London), which is 27.6 mi (44.4 km) away.

If you'd rather travel by train, the main station is Madison Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Madison?
Houses are the most popular kind of holiday home in Madison, according to our data. Even if you have a different idea in mind, Bookabach has properties in a variety of sizes and shapes. Take a look at our options to find your ideal match.
How much does it cost to rent a holiday home in Madison?
Length of stay, property type and time of year are some factors that can influence the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy country cottages to expansive villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Madison?
Prices for beach houses in Madison can differ depending on the size and type of the property and when you’re travelling. All you need to do is enter your travel dates into Bookabach and the number of guests to view your options and prices. From there you can use our filter tool to narrow your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Madison?
Yes. There are. You can pick from 48 holiday homes that allow pets in Madison. Several of our pet-friendly holiday homes have an outdoor space for your four-legged pal to play in, doggie beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Bookabach.
Can I rent a house with a pool in Madison?
Add another level of fun to your trip by booking your family into one of the seven houses with a private pool in Madison. Use our search filter to find the kind of property you want on Bookabach, and then spend lazy days splashing and playing in a swimming pool that’s only for you.
What are popular home amenities in Madison?
When it comes to home amenities that guests are searching for in Madison, an ocean view, an electric car charging station and nearby museums are the most popular. With Bookabach holiday homes, you’ll have options to fit your style and taste, whether you’re going on a trip with family, friends or even pets.
Are there large group holiday homes in Madison?
Madison has 10 holiday homes that can host 10 or more guests. These stays come with the space you need to share good times with friends and family.
Are there holiday homes in Madison that welcome kids?
Gather your entire family for the adventure of a lifetime in Madison at one of our 48 family-friendly properties. A lot of these stays come with amenities that are perfect for getaways with the little ones, including full kitchens, extra bedrooms and swimming pools. Simply click on the “Properties good for families” filter and pick your favourite.
What are the top attractions for families in Madison?
Keeping the kids happy during your holiday in Madison is easy with these awesome family-friendly attractions:

  • Hammonasset Beach
  • Hammonasset Beach State Park
  • Bishops Orchard and Winery

Are there one-bedroom holiday homes in Madison?
You can choose from two one-bedroom homes in Madison. Whether you want a comfy cottage or a fancy condo, our one-bedroom properties are ideal if you don’t need loads of space. One of the main perks of having your own place? You’ll never need to share your trip with strangers.
Can I find two-bedroom holiday homes in Madison?
Madison has eight two-bedroom holiday properties to select from. Discover a holiday home with all the space and comfort you’re looking for at a price that’s hard to resist on Bookabach.
Are there holiday homes with WiFi in Madison?
Whether you’d like to keep up with the news, look over emails or post a pic to social media, there are 26 holiday homes with WiFi in Madison. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Madison?
Choose from 45 holiday homes with air conditioning in Madison offering that gentle, cool breeze and extra comfort level. Just enter your chosen travel dates and then take advantage of our filters to help you book properties with air conditioning.
How old do you have to be to rent a holiday home in Madison?
The minimum required age is usually 16, 18 or 21. It can vary from property to property on Bookabach, so look at the rules of your preferred Madison stay before booking.
How long can I rent a holiday home in Madison for?
How long you can rent a holiday home in Madison differs according to the property. Just enter your preferred dates to display a list of options offering extended stays. With loads of features such as air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you’re sure to get the perfect place to call your home away from home in Madison.

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