Madison holiday rentals

We found 443 holiday rentals — enter your dates for availability

Select from 34 homes, 10 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.

Holiday rentals with weekly discounts – Madison

Showing deals for:2 Oct - 9 Oct

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Why visit Madison

  • Coastal Charm: Enjoy scenic views of sandy beaches and refreshing coastal walks.
  • Historic Heritage: Explore historic houses and landmarks steeped in local history.
  • Natural Escapes: Revel in outdoor adventures within nearby national and state parks.
  • Quaint Town Centre: Stroll through a charming centre offering family-friendly amenities and local treats.
  • Authentic New England Vibe: Experience a blend of luxury and rustic charm in a delightful coastal retreat.

Popular types of accommodation in Madison

Discover the charm of Madison, Connecticut, where quaint coastal views and historic landmarks create a delightful retreat. Madison holiday rentals offer a range of private holiday homes, cosy cottages, and stylish apartments, perfect for exploring local attractions and scenic walks along the coastline. Whether you're seeking a peaceful escape or a base for cultural exploration, rentals in Madison provide an ideal blend of comfort and authentic New England charm.

  • Private Holiday Homes: The most sought-after choice for visitors seeking a home away from home in Madison is private holiday homes, offering comfort and flexibility.
  • Cottages: Cottages are a charming option for those looking to experience a quaint and cosy retreat in the picturesque surroundings of Madison.
  • Apartments: For a more urban experience, apartments provide a convenient and stylish space for holidaymakers exploring Madison.
  • Cabins: Nestled in nature, cabins offer a rustic atmosphere perfect for those wanting to unwind amidst serene landscapes.
  • Condos: Condos present a modern living option, ideal for families or groups wanting shared amenities and a communal vibe.**

Top attractions near Madison

Madison, Connecticut is a charming city offering a blend of outdoor adventures and cultural experiences. Visitors can explore its scenic national and state parks, enjoy the sandy beaches, and delve into its rich history with historic houses. The local attractions promise a delightful mix of natural beauty and heritage, perfect for those seeking an adventure holiday imbued with a touch of British elegance.

  • Westbrook Town Beach: A scenic sandy retreat with a relaxed, coastal ambience located 10km from Madison, ideal for leisurely seaside strolls and picnics.
  • Clinton Town Beach: A charming beach offering a pleasant escape 5km away, perfect for sunbathing and refreshing dips in the sea.
  • Harvey's Beach: A delightful coastal spot 14km from Madison, providing a serene setting to enjoy the rhythmic sound of the waves and the gentle sea breeze.

Things to do recommended for couples

Madison, Connecticut, offers charming coastal strolls along the picturesque shoreline, perfect for couples. Enjoy a romantic picnic at Hammonasset Beach State Park, or explore the quaint shops and delightful dining options in downtown. Don't miss a sunset walk on the scenic boardwalk for an unforgettable experience together.

Things to do recommended for families

Families will enjoy exploring Madison’s scenic coastal areas, with sandy beaches perfect for picnics and seaside walks, and engaging local museums offering interactive displays for children, ensuring a delightful local experience for all ages.

Things to do recommended for groups

Experience the charm of Madison, Connecticut with local group activities and historical walks, exploring its picturesque landscapes and cosy local eateries, perfect for sharing memorable moments with your mates.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Madison

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to refine your search with the appropriate priorities. Here are some Stayz booking tips for you.

  • Traveling to Madison with a group: Consider how many bedrooms you might require, along with features like a fully equipped kitchen or an outdoor area suited for group get-togethers. Fortunately, Stayz offers filters to help you find these and many other desired amenities.
  • Traveling to Madison with young kids: Traveling with young children can prove demanding. It is essential to prioritise their comfort and safety, along with providing suitable facilities, such as a private swimming pool. Additionally, it is wise to take into account your closeness to attractions that cater to families.
  • Taking your pets with you to Madison: For many, a family holiday is simply not complete without their four-legged companion by their side. If you share this sentiment, consider exploring Stayz accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels right at home.
  • Planning for a long term stay visiting Madison: If you're seeking holiday lets with discounts for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Consider including a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Madison

Madison offers an exceptional coastal getaway experience with its scenic views and family-friendly atmosphere. Visitors can enjoy the city's charming Madison centre and a variety of local amenities, perfect for a relaxed outdoor adventure. The blend of luxury and recreational vibes, coupled with friendly locals, promises a delightful family retreat in this picturesque destination.

  • Old Saybrook: Old Saybrook is a charming city located 16km from Madison, offering a delightful blend of scenic beauty and romantic experiences. Visitors can immerse themselves in the great outdoors with activities at nearby recreational areas, or enjoy a round of golf at the local course. The city is also well known for its beachside attractions, including a family beach and a national state park that provide stunning backdrops for leisurely walks and picturesque picnics.
  • Westbrook: Westbrook, a picturesque city situated 11km from Madison, promises an engaging travel experience with an emphasis on outdoor charm, romance, and captivating scenery. Here, travellers can enjoy a variety of activities such as attending music concerts, playing golf on well-maintained courses, or simply relaxing at local resorts. The city’s appealing landmarks include a family beach and an event conference venue, making it a wonderful destination for both cultural and natural exploration.
  • Clinton: Clinton is a delightful city just 3km from Madison, offering a perfect mix of outdoor adventure, scenic views and excitement. Visitors are invited to explore expansive recreational areas, test their skills on local golf courses, or indulge in a spot of shopping at local centres. With its close proximity to a family beach and a national state park, Clinton provides an ideal setting for both leisurely strolls and more invigorating outdoor pursuits.

Best time to go to Madison

If you're planning a trip to Madison, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnyAverageModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageModerately Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyModerately HighModerately High
July73.8°F (23.2°C)Light RainMostly SunnyModerately HighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyModerately HighModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyModerately LowAverage
November45.5°F (7.5°C)Light RainMostly SunnyModerately LowAverage
December37.8°F (3.2°C)Light RainMostly SunnyModerately LowAverage

Booking with Stayz is a breeze

Are you hoping to make your next journey more affordable? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, feel free to utilise our filters to sort by price, location, and the type of holiday rental you prefer.

Stayz Trips: Planning made easy

Stayz's innovative Trip Board offers you a convenient space to plan new adventures, pick up from where you last left off, or easily view and organise your travel plans. The properties you've previously saved and booked are now conveniently categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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:

  • Chatfield Hollow State Park (4.9 mi / 8 km)
  • Gouveia Winery (13.9 mi / 22.4 km)
  • Paradise Hills Vineyard (14.4 mi / 23.2 km)
  • 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)

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)
  • Chatfield Hollow State Park (4.9 mi / 8 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)

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, Stayz 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 Stayz 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 Stayz 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 Stayz.
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 Stayz, 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 Stayz 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 Stayz.
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 Stayz 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 Stayz, 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.