Photo by Shannon Willitts

Madison holiday lettings

We found 435 holiday rentals — enter your dates for availability

Select from 34 homes, 12 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:10 Oct - 17 Oct

Why visit Madison

  • Outdoor Adventures: Madison offers a plethora of outdoor activities, including national parks and picturesque beaches, perfect for nature lovers.
  • Charming Downtown: Explore the vibrant Madison Centre with friendly locals and a welcoming atmosphere, ideal for leisurely strolls.
  • Family-Friendly Vibe: The coastal regions provide a delightful setting for family outings and scenic enjoyment.
  • Relaxing Cinemas: Unwind in the evenings at local cinemas after a day of exploration.
  • Diverse Accommodation: Choose from private vacation homes, charming cottages, and stylish apartments to suit your preferences and budget.

Popular types of accommodation in Madison

If you're considering a getaway to Madison, you're in for a treat! Our most sought-after accommodation options include Houses, charming Cottages, and stylish Apartments. Whether you're looking for apartment rentals, house rentals, or cosy home rentals, we provide a wide array of rental listings in Madison to ensure you find the perfect stay. Enjoy your holiday with transparency, savings, and peace of mind.

  • Houses: The top choice for visitors in Madison, offering spacious and comfortable settings for families or groups.
  • Cottages: A charming option, these quaint retreats provide a homely atmosphere near the picturesque coastline.
  • Apartments: Ideal for solo travellers or couples, these provide a convenient and stylish base for exploring Madison.
  • Cabins: A rustic escape, perfect for those seeking a tranquil retreat surrounded by nature.
  • Condos: A modern alternative, these offer amenities and are often located in vibrant areas for easy access to local attractions.**

Top attractions in and around Madison

Madison, Connecticut, is an excellent destination for outdoor enthusiasts and adventure seekers, boasting a range of attractions such as national parks, picturesque beaches, and a railway museum. Visitors can immerse themselves in the local culture while enjoying various outdoor activities. Additionally, Madison's cinemas provide a delightful option for a relaxing evening after a day of exploration.

  • Hammonasset Beach State Park: This expansive park offers a delightful blend of outdoor adventure and stunning scenery. Enjoy hiking, picnicking, and birdwatching, or simply relax amidst the natural beauty of the Connecticut shoreline.
  • Hammonasset Beach: A lovely stretch of sandy shore, perfect for sunbathing, swimming, and beachcombing. The tranquil waters and picturesque views create a relaxing seaside atmosphere.
  • Essex Steam Train: Just 6.2km away, this charming railway museum provides a nostalgic journey through history with scenic rides aboard vintage steam locomotives, immersing you in the region's rich culture.

Things to do recommended for couples

For a romantic getaway in Madison, visit Chamard Vineyards for delightful wine tasting, indulge in a meal at Anna Mia's for a cosy atmosphere, or embrace adventure at Powder Ridge Mountain Park for skiing. Each spot offers a unique charm perfect for couples.

Things to do recommended for families

During your family vacation in Madison, Connecticut, enjoy thrilling activities such as the Connecticut Sportsplex for sports enthusiasts, Stay and Play LLC for arcade adventures, and the charming Greenport Carousel for a delightful outdoor experience with the family.

Things to do recommended for groups

Explore the Clinton Crossing Premium Outlets for a delightful shopping experience, just 1.2km from Madison. Visit RJ Julia Booksellers for a literary adventure, or head to the North Madison Shopping Centre, where you can enjoy a vibrant atmosphere filled with family-friendly options.

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming holiday? It might be worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Madison

Madison, Connecticut, offers a delightful blend of outdoor adventures and scenic beauty, ideal for a memorable getaway. Explore the charming Madison Centre and the vibrant downtown area, where you'll find friendly locals and a welcoming atmosphere. Nearby, enjoy the family-friendly vibe of the coastal regions and picturesque landscapes. Whether you're seeking luxury or a relaxing budget break, Madison promises a unique experience that caters to all tastes and preferences.

  • Westbrook: Situated approximately 4.3km from Madison, Westbrook is a charming coastal town known for its stunning outdoor experiences and romantic scenery. Visitors are drawn to its beautiful beaches, making it an ideal spot for a relaxing day by the sea. The local resorts offer a perfect getaway, while music concerts provide entertainment throughout the year. Don't miss the recreational areas where you can engage in various outdoor activities. Whether it's sunbathing on the family beach or attending an event at the conference venue, Westbrook promises a delightful escape.
  • Old Saybrook: Located around 6.2km from Madison, Old Saybrook enchants visitors with its picturesque landscapes and outdoor adventures. This quaint town is famous for its scenic beaches and tranquil lake, offering plenty of opportunities for a romantic stroll or a peaceful day by the water. Golf enthusiasts can enjoy the local courses, while music concerts in the area provide a lively atmosphere. With its charming waterfront and recreational areas, Old Saybrook is a perfect destination for those seeking both relaxation and adventure.
  • Clinton: Just 1.2km from Madison, Clinton is a vibrant town that beckons adventurers and nature lovers alike. Known for its stunning beaches and access to a national state park, Clinton offers countless outdoor activities, from hiking to swimming. Visitors can indulge in the lively music scene, enjoy delightful resort stays, and explore the recreational areas that define this coastal gem. With its proximity to Madison, Clinton is an ideal spot for a quick escape into nature and excitement.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

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

When travelling with a group, family, pets, or if you're seeking longer stays, it's essential to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Madison with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Madison with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Madison: For many families, a trip wouldn’t feel complete without their beloved four-legged companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Madison: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a lovely kitchen, or even a private pool in your search criteria.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume previous arrangements, or manage your travel itineraries. You can easily find the properties you’ve saved or booked, neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring the Trip Boards, simply visit: https://www.vrbo.com/en-gb/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:

  • Chamard Vineyards (1.6 mi / 2.6 km)
  • Chatfield Hollow State Park (4.9 mi / 8 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)
  • Sparkling Pointe (17.6 mi / 28.3 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)
  • 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 rental accommodation in Madison?
Houses are the most popular kind of holiday rental in Madison, according to our data. Even if you have a different idea in mind, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo 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 rentals in Madison?
Yes. There are. You can pick from 48 holiday rentals that allow pets in Madison. Several of our pet-friendly holiday rentals 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 Vrbo.
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 Vrbo, and then spend lazy days splashing and playing in a swimming pool that's only for you.
What are popular rental amenities in Madison?
When it comes to rental amenities that guests are searching for in Madison, an ocean view, an electric car charging station and nearby museums are the most popular. With Vrbo 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 rentals 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 rentals 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 rentals in Madison?
You can choose from two one-bedroom rentals 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 rentals 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 Vrbo.
Are there holiday rentals 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 Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Madison?
Choose from 45 holiday rentals 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 rental in Madison?
The minimum required age is usually 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred Madison stay before booking.
How long can I rent a holiday rental in Madison for?
How long you can rent a holiday rental 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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